node_modules: update (#344)

Co-authored-by: dawidd6 <9713907+dawidd6@users.noreply.github.com>

node_modules/.package-lock.json

@@ -94,9 +94,9 @@
       }
     },
     "node_modules/nodemailer": {
-      "version": "10.0.15",
+      "version": "10.1.0",
-      "resolved": "https://registry.npmjs.org/nodemailer/-/nodemailer-10.0.15.tgz",
+      "resolved": "https://registry.npmjs.org/nodemailer/-/nodemailer-10.1.0.tgz",
-      "integrity": "sha512-EUqp5PhtcsYXs9Fq/lS7s/8zlTrnBqmzZWzFFROrNikMiz+om/YRKMwqN907t+0A1KKyT8jd39CBUbFZmaZmcA==",
+      "integrity": "sha512-fXW8AulB25aOTuwfRYV6lqHyfz2VM4rr4SGXH03mE7x5znEUpzL5mu6anARUpZN7744Ziwkmr4AxSLPJsBQspg==",
       "license": "MIT-0",
       "engines": {
         "node": ">=20.0.0"

node_modules/nodemailer/CHANGELOG.md

@@ -1,5 +1,41 @@
 # CHANGELOG
 
+## [10.1.0](https://github.com/nodemailer/nodemailer/compare/v10.0.16...v10.1.0) (2026-10-10)
+
+
+### Features
+
+* harden message streams, SMTP connections and the connection pool ([8009da6](https://github.com/nodemailer/nodemailer/commit/8009da6e10bb8e10d7f0948a25d65895fdcd64f1))
+
+
+### Bug Fixes
+
+* do not read the environment or the interface table on import ([094179d](https://github.com/nodemailer/nodemailer/commit/094179d176d2ebe7a28742411ad427d3c87a3981))
+* end the SMTP session on any 421 reply and drive the envelope through one step ([5638ac1](https://github.com/nodemailer/nodemailer/commit/5638ac1914342460df270f736e7ceb0a844cf83a))
+* keep ERR_ACCESS_DENIED from the Node.js permission model ([8b33a3d](https://github.com/nodemailer/nodemailer/commit/8b33a3d4fedee3431b97da7da12af954c3c8dceb))
+* let the proxy handshake and the SMTP connection share one deadline ([91ed683](https://github.com/nodemailer/nodemailer/commit/91ed683f7a1e9ff8c56e24fb76facf16af08b162))
+* **mime-node:** decode an SMTPUTF8 domain from its A-label form ([e436f4d](https://github.com/nodemailer/nodemailer/commit/e436f4dccbc8b0fb57b4747ebaafa5bb035c15cb))
+* **mime-node:** finish an encoded part only after its output was read ([ec97d8f](https://github.com/nodemailer/nodemailer/commit/ec97d8f679a1d9d47bbebb03ea064f5fa6f58d01))
+* **qp:** encode a lone CR or LF in binary quoted-printable parts ([42b91d9](https://github.com/nodemailer/nodemailer/commit/42b91d9a0fe18eea412c9774c5c142adf5b3efc7))
+* **smtp-connection:** count the wait for the greeting against connectionTimeout ([bdcd046](https://github.com/nodemailer/nodemailer/commit/bdcd0462cab163eca3c34058d09b9981ab671c47))
+* **smtp-connection:** drop the connection when DATA is taken after a refused sender ([f90fb04](https://github.com/nodemailer/nodemailer/commit/f90fb045bc24f96a128710791b2fa443e64f55fd))
+* **smtp-connection:** refuse a second connect() call ([24ba2e0](https://github.com/nodemailer/nodemailer/commit/24ba2e0847ecb8202540f1c5e53483bd119ae4f2))
+* turn Nagle off for SMTP sockets and report an early sendmail exit as such ([fa9b8d3](https://github.com/nodemailer/nodemailer/commit/fa9b8d300bf642cd9e11f6732ebb312c09868677))
+
+
+### Performance Improvements
+
+* encode base64 and quoted-printable without per-chunk delays ([fd377bb](https://github.com/nodemailer/nodemailer/commit/fd377bbf559363860aedbedba6f107348fc152d2))
+
+## [10.0.16](https://github.com/nodemailer/nodemailer/compare/v10.0.15...v10.0.16) (2026-10-07)
+
+
+### Bug Fixes
+
+* **addressparser:** keep an escaped parenthesis inside a comment ([c4ae20d](https://github.com/nodemailer/nodemailer/commit/c4ae20d074ac0510cc2d0cbd6039ee7fab3a4ca8))
+* **fetch:** keep the case of cookie names ([#1888](https://github.com/nodemailer/nodemailer/issues/1888)) ([9f16eed](https://github.com/nodemailer/nodemailer/commit/9f16eedf8de0485e6d07969113db992ff70f89ce))
+* **fetch:** read the cookie name-value pair by position ([645e97c](https://github.com/nodemailer/nodemailer/commit/645e97c8f0586404d9fb861c9527be7572c2c832))
+
 ## [10.0.15](https://github.com/nodemailer/nodemailer/compare/v10.0.14...v10.0.15) (2026-10-05)
 
 

node_modules/nodemailer/dist/cjs/addressparser/index.js

@@ -670,7 +670,11 @@ class Tokenizer {
             this.escaped = false;
             return;
         }
-        else if (['"', "'"].includes(this.operatorExpecting) && chr === '\\') {
+        else if (['"', "'", ')'].includes(this.operatorExpecting) && chr === '\\') {
+            // A backslash escapes the next character inside a quoted string and inside a
+            // comment alike (RFC 5322 3.2.2, ccontent includes quoted-pair). Honouring it
+            // only in quoted strings let an escaped parenthesis close the comment, which
+            // released the rest of it, an address included, into the header
             this.escaped = true;
             return;
         }

node_modules/nodemailer/dist/cjs/base64/index.d.ts

@@ -24,6 +24,9 @@ export interface EncoderOptions {
 /**
  * Creates a transform stream for encoding data to base64 encoding
  *
+ * The output is the same as `wrap(encode(input), lineLength)` no matter how the input is split
+ * into chunks: every line but the last one ends with a line break, the last one does not
+ *
  * @constructor
  * @param options Stream options
  * @param [options.lineLength=76] Maximum length for lines, set to false to disable wrapping

node_modules/nodemailer/dist/cjs/base64/index.js

@@ -16,6 +16,47 @@ function encode(buffer) {
     }
     return buffer.toString('base64');
 }
+/**
+ * Turns a line length option into a whole number of characters, the default for anything unusable
+ */
+function normalizeLineLength(lineLength) {
+    const length = Math.floor(Number(lineLength));
+    return Number.isFinite(length) && length >= 1 ? length : 76;
+}
+/**
+ * Splits the bytes of `src` into lines of `lineLength` bytes, each followed by a line break. With
+ * `final` set the last line, which may be shorter, gets no line break; otherwise only complete
+ * lines are taken and the rest is left for the caller
+ *
+ * @param src Bytes to wrap
+ * @param lineLength Line length
+ * @param final Whether `src` ends the output
+ * @returns The wrapped bytes and the number of trailing bytes not taken
+ */
+function wrapBuffer(src, lineLength, final) {
+    const lines = Math.ceil(src.length / lineLength);
+    // the last line waits for more data unless this is the end: whether it gets a line break
+    // depends on whether anything follows it
+    const complete = Math.max(lines - 1, 0);
+    let rest = src.length - complete * lineLength;
+    const output = Buffer.allocUnsafe(complete * (lineLength + 2) + (final ? rest : 0));
+    let to = 0;
+    for (let from = 0; from < complete * lineLength; from += lineLength) {
+        src.copy(output, to, from, from + lineLength);
+        to += lineLength;
+        output[to++] = 0x0d;
+        output[to++] = 0x0a;
+    }
+    if (final) {
+        to += src.copy(output, to, complete * lineLength);
+        rest = 0;
+    }
+    if (to !== output.length) {
+        // never hand out bytes of the unfilled allocation
+        throw new Error('Unexpected wrapped length');
+    }
+    return { output, rest };
+}
 /**
  * Adds soft line breaks to a base64 string
  *
@@ -44,6 +85,9 @@ function wrap(str, lineLength) {
 /**
  * Creates a transform stream for encoding data to base64 encoding
  *
+ * The output is the same as `wrap(encode(input), lineLength)` no matter how the input is split
+ * into chunks: every line but the last one ends with a line break, the last one does not
+ *
  * @constructor
  * @param options Stream options
  * @param [options.lineLength=76] Maximum length for lines, set to false to disable wrapping
@@ -53,66 +97,61 @@ class Encoder extends node_stream_1.Transform {
         super();
         this.options = options || {};
         if (this.options.lineLength !== false) {
-            this.options.lineLength = this.options.lineLength || 76;
+            this.options.lineLength = normalizeLineLength(this.options.lineLength);
         }
         this._curLine = '';
         this._remainingBytes = false;
         this.inputBytes = 0;
         this.outputBytes = 0;
     }
+    /**
+     * Emits the encoded characters `b64` that follow the current line, keeping what can not be
+     * emitted yet as the new current line
+     *
+     * @internal
+     */
+    _emit(b64, final) {
+        const src = Buffer.from(this._curLine + b64, 'latin1');
+        if (!src.length) {
+            return;
+        }
+        let output = src;
+        if (this.options.lineLength) {
+            const wrapped = wrapBuffer(src, this.options.lineLength, final);
+            output = wrapped.output;
+            this._curLine = wrapped.rest ? src.toString('latin1', src.length - wrapped.rest) : '';
+        }
+        else {
+            this._curLine = '';
+        }
+        if (output.length) {
+            this.outputBytes += output.length;
+            this.push(output);
+        }
+    }
     /** @internal */
     _transform(chunk, encoding, done) {
         let buf = encoding !== 'buffer' ? Buffer.from(chunk, encoding) : chunk;
         if (!buf || !buf.length) {
-            setImmediate(done);
+            return done();
-            return;
         }
         this.inputBytes += buf.length;
-        if (this._remainingBytes && this._remainingBytes.length) {
+        if (this._remainingBytes) {
             buf = Buffer.concat([this._remainingBytes, buf], this._remainingBytes.length + buf.length);
             this._remainingBytes = false;
         }
-        if (buf.length % 3) {
+        const extra = buf.length % 3;
-            this._remainingBytes = buf.slice(buf.length - (buf.length % 3));
+        if (extra) {
-            buf = buf.slice(0, buf.length - (buf.length % 3));
+            this._remainingBytes = buf.subarray(buf.length - extra);
+            buf = buf.subarray(0, buf.length - extra);
         }
-        else {
+        this._emit(encode(buf), false);
-            this._remainingBytes = false;
+        done();
-        }
-        let b64 = this._curLine + encode(buf);
-        if (this.options.lineLength) {
-            b64 = wrap(b64, this.options.lineLength);
-            // remove last line as it is still most probably incomplete
-            const lastLF = b64.lastIndexOf('\n');
-            if (lastLF < 0) {
-                this._curLine = b64;
-                b64 = '';
-            }
-            else if (lastLF === b64.length - 1) {
-                this._curLine = '';
-            }
-            else {
-                this._curLine = b64.substring(lastLF + 1);
-                b64 = b64.substring(0, lastLF + 1);
-            }
-        }
-        if (b64) {
-            this.outputBytes += b64.length;
-            this.push(Buffer.from(b64, 'ascii'));
-        }
-        setImmediate(done);
     }
     /** @internal */
     _flush(done) {
-        if (this._remainingBytes && this._remainingBytes.length) {
+        this._emit(this._remainingBytes ? encode(this._remainingBytes) : '', true);
-            this._curLine += encode(this._remainingBytes);
+        this._remainingBytes = false;
-        }
-        if (this._curLine) {
-            this._curLine = wrap(this._curLine, this.options.lineLength);
-            this.outputBytes += this._curLine.length;
-            this.push(Buffer.from(this._curLine, 'ascii'));
-            this._curLine = '';
-        }
         done();
     }
 }

node_modules/nodemailer/dist/cjs/dkim/index.js

@@ -37,34 +37,47 @@ class DKIMSigner {
         this.output = output;
         this.output.usingCache = false;
         this.hasErrored = false;
-        this.input.on('error', err => {
+        this.input.on('error', err => this.fail(err));
+        // A consumer that goes away before the signed message was read in full destroys the
+        // output. Stop reading the input and drop the cache file instead of leaving them open
+        this.output.once('close', () => {
+            if (this.output.writableFinished) {
+                return;
+            }
+            this.hasErrored = true;
+            this.input.unpipe();
+            this.input.destroy();
+            this.cleanup();
+        });
+    }
+    /**
+     * Ends the output with an error and releases the cache file
+     */
+    fail(err) {
         this.hasErrored = true;
         this.cleanup();
-            output.emit('error', err);
+        this.output.destroy(err);
-        });
     }
     cleanup() {
         if (!this.cache || !this.cachePath) {
             return;
         }
+        const cache = this.cache;
+        this.cache = false;
+        cache.destroy();
         node_fs_1.default.unlink(this.cachePath, () => false);
     }
     createReadCache() {
         // pipe remainings to cache file
         this.cache = node_fs_1.default.createReadStream(this.cachePath);
-        this.cache.once('error', err => {
+        this.cache.once('error', err => this.fail(err));
-            this.cleanup();
-            this.output.emit('error', err);
-        });
         this.cache.once('close', () => {
             this.cleanup();
         });
         this.cache.pipe(this.output);
     }
     sendNextChunk() {
-        if (this.hasErrored) {
+        while (!this.hasErrored) {
-            return;
-        }
             if (this.readPos >= this.chunks.length) {
                 if (!this.cache) {
                     this.output.end();
@@ -79,9 +92,12 @@ class DKIMSigner {
                 });
                 return;
             }
-        setImmediate(() => this.sendNextChunk());
+        }
     }
     sendSignedOutput() {
+        if (this.hasErrored) {
+            return;
+        }
         let keyPos = 0;
         const signNextKey = () => {
             if (keyPos >= this.keys.length) {
@@ -101,9 +117,7 @@ class DKIMSigner {
                 });
             }
             catch (err) {
-                this.hasErrored = true;
+                this.fail(err);
-                this.cleanup();
-                this.output.emit('error', err);
                 return;
             }
             if (dkimField) {
@@ -122,7 +136,6 @@ class DKIMSigner {
         // pipe remainings to cache file
         this.cache = node_fs_1.default.createWriteStream(this.cachePath);
         this.cache.once('error', err => {
-            this.cleanup();
             // drain input
             this.relaxedBody.unpipe(this.cache);
             this.relaxedBody.on('readable', () => {
@@ -130,11 +143,12 @@ class DKIMSigner {
                     // do nothing
                 }
             });
-            this.hasErrored = true;
+            this.fail(err);
-            // emit error
-            this.output.emit('error', err);
         });
         this.cache.once('close', () => {
+            if (this.hasErrored) {
+                return;
+            }
             this.sendSignedOutput();
         });
         this.relaxedBody.removeAllListeners('readable');
@@ -211,7 +225,7 @@ class DKIM {
             catch (_E) {
                 // the body hash is created here, an unknown hashAlgo throws inside this timer
                 // where nothing else could catch it
-                output.emit('error', sign_js_1.default.unsupportedHashAlgoError(signer.hashAlgo));
+                signer.fail(sign_js_1.default.unsupportedHashAlgoError(signer.hashAlgo));
                 return;
             }
             if (writeValue) {

node_modules/nodemailer/dist/cjs/dkim/message-parser.js

@@ -107,7 +107,7 @@ class MessageParser extends node_stream_1.Transform {
                 const chunk = data.slice(headerPos);
                 this.bodySize += chunk.length;
                 // this would be the first chunk of data sent downstream
-                setImmediate(() => this.push(chunk));
+                this.push(chunk);
             }
             return false;
         }
@@ -136,7 +136,7 @@ class MessageParser extends node_stream_1.Transform {
             this.bodySize += chunk.length;
             this.push(chunk);
         }
-        setImmediate(callback);
+        callback();
     }
     /** @internal */
     _flush(callback) {

node_modules/nodemailer/dist/cjs/errors.d.ts

@@ -61,6 +61,19 @@ export declare const EPROXY = "EPROXY";
 export declare const EFILEACCESS = "EFILEACCESS";
 export declare const EURLACCESS = "EURLACCESS";
 export declare const EFETCH = "EFETCH";
+/**
+ * Tells whether the error ended the connection rather than rejected what was sent over it
+ */
+export declare const isTransientError: (err: {
+    code?: string | undefined;
+    responseCode?: number | undefined;
+}) => boolean;
+/**
+ * Code Node.js sets on an error when its permission model (`--permission`) denies an
+ * operation. It is not replaced with the Nodemailer code of the failing step (`ESOCKET`,
+ * `EDNS`, `EFETCH`, ...), so a missing grant such as `--allow-net` stays recognizable.
+ */
+export declare const ERR_ACCESS_DENIED = "ERR_ACCESS_DENIED";
 /**
  * An Error together with the properties Nodemailer attaches to the errors it
  * hands to callers. Every property is optional, the set that is present
@@ -84,6 +97,10 @@ export interface NodemailerError extends NodeJS.ErrnoException {
     rejected?: string[] | undefined;
     /** Per-recipient errors for the rejected addresses */
     rejectedErrors?: NodemailerError[] | undefined;
+    /** The code the error had before Nodemailer set its own, such as ECONNREFUSED for an ESOCKET error */
+    originalCode?: string | undefined;
+    /** Which wait an ETIMEDOUT error ended: connecting, the greeting, a TLS upgrade or an idle socket */
+    timeoutType?: 'CONNECT_TIMEOUT' | 'GREETING_TIMEOUT' | 'UPGRADE_TIMEOUT' | 'SOCKET_TIMEOUT' | undefined;
 }
 /**
  * Node style callback: called with an error, or with null and the result

node_modules/nodemailer/dist/cjs/errors.js

@@ -10,7 +10,7 @@
  *   err.code = errors.ECONNECTION;
  */
 Object.defineProperty(exports, "__esModule", { value: true });
-exports.EFETCH = exports.EURLACCESS = exports.EFILEACCESS = exports.EPROXY = exports.ECONFIG = exports.ESES = exports.ESENDMAIL = exports.EMAXRECIPIENTS = exports.EMAXLIMIT = exports.EOAUTH2 = exports.ENOAUTH = exports.EAUTH = exports.ESTREAM = exports.EMESSAGE = exports.EENVELOPE = exports.EPROTOCOL = exports.EREQUIRETLS = exports.ETLS = exports.EDNS = exports.ESOCKET = exports.ETIMEDOUT = exports.ECONNECTION = exports.ERROR_CODES = void 0;
+exports.ERR_ACCESS_DENIED = exports.isTransientError = exports.EFETCH = exports.EURLACCESS = exports.EFILEACCESS = exports.EPROXY = exports.ECONFIG = exports.ESES = exports.ESENDMAIL = exports.EMAXRECIPIENTS = exports.EMAXLIMIT = exports.EOAUTH2 = exports.ENOAUTH = exports.EAUTH = exports.ESTREAM = exports.EMESSAGE = exports.EENVELOPE = exports.EPROTOCOL = exports.EREQUIRETLS = exports.ETLS = exports.EDNS = exports.ESOCKET = exports.ETIMEDOUT = exports.ECONNECTION = exports.ERROR_CODES = void 0;
 /**
  * Error code descriptions for documentation and debugging
  */
@@ -68,3 +68,14 @@ exports.EPROXY = 'EPROXY';
 exports.EFILEACCESS = 'EFILEACCESS';
 exports.EURLACCESS = 'EURLACCESS';
 exports.EFETCH = 'EFETCH';
+/**
+ * Tells whether the error ended the connection rather than rejected what was sent over it
+ */
+const isTransientError = (err) => err.responseCode === 421 || err.code === exports.ECONNECTION || err.code === exports.ESOCKET || err.code === exports.ETIMEDOUT;
+exports.isTransientError = isTransientError;
+/**
+ * Code Node.js sets on an error when its permission model (`--permission`) denies an
+ * operation. It is not replaced with the Nodemailer code of the failing step (`ESOCKET`,
+ * `EDNS`, `EFETCH`, ...), so a missing grant such as `--allow-net` stays recognizable.
+ */
+exports.ERR_ACCESS_DENIED = 'ERR_ACCESS_DENIED';

node_modules/nodemailer/dist/cjs/fetch/cookies.js

@@ -130,19 +130,31 @@ class Cookies {
      */
     parse(cookieStr) {
         const cookie = {};
+        let hasNameValue = false;
         (cookieStr || '')
             .toString()
             .split(';')
             .forEach(cookiePart => {
-            const valueParts = cookiePart.split('=');
+            if (!cookiePart.trim()) {
-            const key = valueParts.shift().trim().toLowerCase();
-            let value = valueParts.join('=').trim();
-            let domain;
-            if (!key) {
                 // skip empty parts
                 return;
             }
-            switch (key) {
+            const valueParts = cookiePart.split('=');
+            const name = valueParts.shift().trim();
+            let value = valueParts.join('=').trim();
+            let domain;
+            // the first part is always the name-value pair, so a cookie named
+            // like an attribute is not mistaken for one (RFC 6265 section 5.2)
+            if (!hasNameValue) {
+                hasNameValue = true;
+                if (name) {
+                    // cookie names are case-sensitive, only attribute names are not
+                    cookie.name = name;
+                    cookie.value = value;
+                }
+                return;
+            }
+            switch (name.toLowerCase()) {
                 case 'expires': {
                     const expires = new Date(value);
                     // ignore date if can not parse it
@@ -170,11 +182,6 @@ class Cookies {
                 case 'httponly':
                     cookie.httponly = true;
                     break;
-                default:
-                    if (!cookie.name) {
-                        cookie.name = key;
-                        cookie.value = value;
-                    }
             }
         });
         return cookie;

node_modules/nodemailer/dist/cjs/fetch/index.js

@@ -81,6 +81,17 @@ const TLS_OPTION_KEYS = [
     'sessionIdContext',
     'sigalgs'
 ];
+/**
+ * Marks an error of the request as a fetch error, unless it is a permission model
+ * denial, which keeps its own code (see ERR_ACCESS_DENIED)
+ *
+ * @param err Error to mark
+ */
+function setFetchCode(err) {
+    if (err.code !== errors.ERR_ACCESS_DENIED) {
+        err.code = errors.EFETCH;
+    }
+}
 /**
  * Resolves a URL only if it is one this module is willing to request.
  *
@@ -177,7 +188,7 @@ function nmfetch(url, options) {
                     return;
                 }
                 finished = true;
-                err.code = errors.EFETCH;
+                setFetchCode(err);
                 err.sourceUrl = url;
                 fetchRes.emit('error', err);
             });
@@ -250,7 +261,7 @@ function nmfetch(url, options) {
     catch (E) {
         finished = true;
         setImmediate(() => {
-            E.code = errors.EFETCH;
+            setFetchCode(E);
             E.sourceUrl = url;
             fetchRes.emit('error', E);
         });
@@ -262,7 +273,7 @@ function nmfetch(url, options) {
             return;
         }
         finished = true;
-        err.code = errors.EFETCH;
+        setFetchCode(err);
         err.sourceUrl = sourceUrl;
         fetchRes.emit('error', err);
         req.abort();
@@ -272,6 +283,15 @@ function nmfetch(url, options) {
         req.setTimeout(timeout, () => fail(new Error('Request Timeout')));
     }
     req.on('error', (err) => fail(err));
+    // a consumer that destroys the response stream before it ended does not want the rest of
+    // the body, release the request now instead of when the timeout fires
+    fetchRes.once('close', () => {
+        if (finished || fetchRes.readableEnded) {
+            return;
+        }
+        finished = true;
+        req.destroy();
+    });
     req.on('response', res => {
         let inflate;
         if (finished) {

node_modules/nodemailer/dist/cjs/mailer/index.js

@@ -157,6 +157,11 @@ class Mail extends node_events_1.EventEmitter {
             this.getSocket = false;
         }
         const mail = new mail_message_js_1.default(this, data);
+        // a failed message is not going to be read anymore, release its content streams
+        const fail = (err) => {
+            mail.releaseStreams();
+            done(err);
+        };
         this.logger.debug({
             tnx: 'transport',
             name: this.transporter.name,
@@ -170,7 +175,7 @@ class Mail extends node_events_1.EventEmitter {
                     tnx: 'plugin',
                     action: 'compile'
                 }, 'PluginCompile Error: %s', err.message);
-                return done(err);
+                return fail(err);
             }
             let recipientCount;
             try {
@@ -187,7 +192,7 @@ class Mail extends node_events_1.EventEmitter {
                     tnx: 'transport',
                     action: 'send'
                 }, 'Compile Error: %s', err.message);
-                return done(err);
+                return fail(err);
             }
             const maxRecipients = mail.data.maxRecipients === undefined ? DEFAULT_MAX_RECIPIENTS : mail.data.maxRecipients;
             if (maxRecipients && recipientCount > maxRecipients) {
@@ -198,7 +203,7 @@ class Mail extends node_events_1.EventEmitter {
                     tnx: 'transport',
                     action: 'send'
                 }, 'Send Error: %s', err.message);
-                return done(err);
+                return fail(err);
             }
             this._processPlugins('stream', mail, err => {
                 if (err) {
@@ -207,7 +212,7 @@ class Mail extends node_events_1.EventEmitter {
                         tnx: 'plugin',
                         action: 'stream'
                     }, 'PluginStream Error: %s', err.message);
-                    return done(err);
+                    return fail(err);
                 }
                 if (mail.data.dkim || this.dkim) {
                     mail.message.processFunc(input => {
@@ -222,6 +227,7 @@ class Mail extends node_events_1.EventEmitter {
                 }
                 this.transporter.send(mail, (...args) => {
                     if (args[0]) {
+                        mail.releaseStreams();
                         this.logger.error({
                             err: args[0],
                             tnx: 'transport',
@@ -289,6 +295,11 @@ class Mail extends node_events_1.EventEmitter {
         // setup socket handler for the mailer object
         this.getSocket = (options, callback) => {
             const protocol = proxy.protocol.replace(/:$/, '').toLowerCase();
+            // The proxy handshake is a part of connecting and draws from the same deadline as the
+            // SMTP connection that follows it: whatever the proxy takes, the connection does not get
+            const configuredTimeout = Number(this.options.connectionTimeout) || 0;
+            const connectStartedAt = Number(options.connectStartedAt) || Date.now();
+            const connectionTimeout = configuredTimeout ? Math.max(connectStartedAt + configuredTimeout - Date.now(), 1) : undefined;
             if (this.meta.has('proxy_handler_' + protocol)) {
                 return this.meta.get('proxy_handler_' + protocol)(proxy, options, callback);
             }
@@ -296,7 +307,7 @@ class Mail extends node_events_1.EventEmitter {
                 // Connect using a HTTP CONNECT method
                 case 'http':
                 case 'https':
-                    (0, http_proxy_client_js_1.default)(proxy.href, options.port, options.host, this.options.tls || {}, (err, socket) => {
+                    (0, http_proxy_client_js_1.default)(proxy.href, options.port, options.host, connectionTimeout ? Object.assign({}, this.options.tls, { timeout: connectionTimeout }) : this.options.tls || {}, (err, socket) => {
                         if (err) {
                             return callback(err);
                         }
@@ -330,6 +341,9 @@ class Mail extends node_events_1.EventEmitter {
                             },
                             command: 'connect'
                         };
+                        if (connectionTimeout) {
+                            connectionOpts.timeout = connectionTimeout;
+                        }
                         if (proxy.username || proxy.password) {
                             const username = proxy.username || '';
                             const password = proxy.password || '';
@@ -359,11 +373,13 @@ class Mail extends node_events_1.EventEmitter {
                     if (node_net_1.default.isIP(proxy.hostname)) {
                         return connect(proxy.hostname);
                     }
-                    return node_dns_1.default.resolve(proxy.hostname, (err, address) => {
+                    // lookup goes through the hosts file and returns an IPv6 address as well,
+                    // the same way a connection to the proxy host would be resolved otherwise
+                    return node_dns_1.default.lookup(proxy.hostname, (err, address) => {
                         if (err) {
                             return callback(err);
                         }
-                        connect(Array.isArray(address) ? address[0] : address);
+                        connect(address);
                     });
                 }
             }

node_modules/nodemailer/dist/cjs/mailer/mail-message.d.ts

@@ -90,6 +90,11 @@ export default class MailMessage<T = SentMessageInfo> {
         [key: string]: any;
     }, key: string | number, options?: ResolveContentOptions | false): Promise<any>;
     resolveAll(callback: MailMessageDataCallback): void;
+    /**
+     * Destroys the content streams of the message once sending failed. A stream that was not
+     * read to the end would otherwise keep the file or the socket behind it open
+     */
+    releaseStreams(): void;
     normalize(callback: MailMessageDataCallback): void;
     setMailerHeader(): void;
     setPriorityHeaders(): void;

node_modules/nodemailer/dist/cjs/mailer/mail-message.js

@@ -174,6 +174,26 @@ class MailMessage {
         };
         setImmediate(() => resolveNext());
     }
+    /**
+     * Destroys the content streams of the message once sending failed. A stream that was not
+     * read to the end would otherwise keep the file or the socket behind it open
+     */
+    releaseStreams() {
+        const data = this.data;
+        const values = [data.html, data.text, data.watchHtml, data.amp, data.raw, data.icalEvent];
+        for (const key of ['attachments', 'alternatives']) {
+            if (Array.isArray(data[key])) {
+                values.push(...data[key]);
+            }
+        }
+        for (const value of values) {
+            if (value && typeof value === 'object') {
+                shared.destroyStream(value);
+                shared.destroyStream(value.content);
+                shared.destroyStream(value.raw);
+            }
+        }
+    }
     normalize(callback) {
         const envelope = this.message.getEnvelope();
         const messageId = this.message.messageId();

node_modules/nodemailer/dist/cjs/mime-node/index.d.ts

@@ -181,7 +181,7 @@ declare class MimeNode {
     childNodes: MimeNode[];
     /** Filename for this node. Useful with attachments */
     filename?: string | undefined;
-    /** Body content, or the error a content stream emitted before it was read */
+    /** Body content */
     content?: MimeNodeContent | Error | undefined;
     /** Lowercase content type, set when the headers are built */
     contentType?: string | undefined;

node_modules/nodemailer/dist/cjs/mime-node/index.js

@@ -71,6 +71,14 @@ const PLAIN_ADDRESS = /^[^\s"(),:;<>@[\\\]]+@[^\s"(),:;<>@[\\\]]+$/;
 // unroutable garbage into mail for a domain the sender never named. None of these
 // characters are legal in a domain, so keep them away from the mapper.
 const URL_PARSER_UNSAFE = /[/\\?#%\x00-\x20\x7F]/;
+// pipeline() needs a callback to not throw, the errors it sees reach the last stream anyway
+const PIPELINE_NOOP = () => false;
+// The error a node streaming into an output that was destroyed stops with
+function abortedError() {
+    const err = new Error('Message stream was closed before the message was generated');
+    err.code = errors.ESTREAM;
+    return err;
+}
 /**
  * Encodes a domain the way browsers, the WHATWG URL Standard and DNS facing resolvers do,
  * which is with UTS-46 mapping applied before the Punycode step.
@@ -90,9 +98,14 @@ const URL_PARSER_UNSAFE = /[/\\?#%\x00-\x20\x7F]/;
  */
 function normalizeDomain(domain, toUnicode) {
     // domainToASCII and domainToUnicode landed in Node 7, the bundled codec covers Node 6
-    const mapper = toUnicode ? node_url_1.default.domainToUnicode : node_url_1.default.domainToASCII;
+    if (typeof node_url_1.default.domainToASCII === 'function' &&
-    if (typeof mapper === 'function' && !URL_PARSER_UNSAFE.test(domain)) {
+        typeof node_url_1.default.domainToUnicode === 'function' &&
-        const mapped = mapper(domain);
+        !URL_PARSER_UNSAFE.test(domain)) {
+        // The U-label form is decoded from the A-label form rather than from the input:
+        // Deno's domainToASCII returns an empty string for a label it cannot decode, while
+        // its domainToUnicode returns the label with U+FFFD in place of the bad part
+        const ascii = node_url_1.default.domainToASCII(domain);
+        const mapped = ascii && toUnicode ? node_url_1.default.domainToUnicode(ascii) : ascii;
         if (mapped) {
             return mapped;
         }
@@ -444,11 +457,7 @@ class MimeNode {
         if (typeof this.content.pipe === 'function') {
             // pre-stream handler. might be triggered if a stream is set as content
             // and 'error' fires before anything is done with this stream
-            this._contentErrorHandler = err => {
+            shared.recordStreamErrors(this.content);
-                this.content.removeListener('error', this._contentErrorHandler);
-                this.content = err;
-            };
-            this.content.once('error', this._contentErrorHandler);
         }
         else if (typeof this.content === 'string') {
             this._isPlainText = mimeFuncs.isPlainText(this.content);
@@ -660,40 +669,45 @@ class MimeNode {
     createReadStream(options) {
         options = options || {};
         const stream = new node_stream_1.PassThrough(options);
-        let outputStream = stream;
-        let transform;
         this.stream(stream, options, err => {
             if (err) {
-                outputStream.emit('error', err);
+                stream.destroy(err);
                 return;
             }
             stream.end();
         });
-        for (let i = 0, len = this._transforms.length; i < len; i++) {
+        // the content streams of the nodes the message did not get to are not going to be read
-            transform =
+        stream.once('close', () => {
-                typeof this._transforms[i] === 'function' ? this._transforms[i]() : this._transforms[i];
+            if (!stream.writableFinished) {
-            outputStream.once('error', err => {
+                this._destroyContentStreams();
-                transform.emit('error', err);
+            }
         });
-            outputStream = outputStream.pipe(transform);
+        // The stages are joined with pipeline, which destroys all of them when any one fails
+        // or is destroyed. An error anywhere reaches the returned stream exactly once, and a
+        // consumer that destroys the returned stream stops the tree from reading its sources
+        const stages = [stream];
+        for (const transform of this._transforms) {
+            stages.push(typeof transform === 'function' ? transform() : transform);
         }
         // ensure terminating newline after possible user transforms
-        transform = new last_newline_js_1.default();
+        stages.push(new last_newline_js_1.default());
-        outputStream.once('error', err => {
+        let outputStream = (0, node_stream_1.pipeline)(stages, PIPELINE_NOOP);
-            transform.emit('error', err);
+        // dkim and stuff. A process function reads its input itself and reports the errors of
+        // that input on its output, so only a consumer abort has to be carried back upstream
+        for (const processFunc of this._processFuncs) {
+            const input = outputStream;
+            outputStream = processFunc(input);
+            if (outputStream !== input) {
+                (0, node_stream_1.finished)(outputStream, err => {
+                    if (err) {
+                        input.destroy();
+                    }
                 });
-        outputStream = outputStream.pipe(transform);
+            }
-        // dkim and stuff
-        for (let i = 0, len = this._processFuncs.length; i < len; i++) {
-            transform = this._processFuncs[i];
-            outputStream = transform(outputStream);
         }
         if (this.newline) {
             const winbreak = ['win', 'windows', 'dos', '\r\n'].includes(this.newline.toString().toLowerCase());
-            const newlineTransform = winbreak ? new le_windows_js_1.default() : new le_unix_js_1.default();
+            outputStream = (0, node_stream_1.pipeline)(outputStream, winbreak ? new le_windows_js_1.default() : new le_unix_js_1.default(), PIPELINE_NOOP);
-            const stream = outputStream.pipe(newlineTransform);
-            outputStream.on('error', err => stream.emit('error', err));
-            return stream;
         }
         return outputStream;
     }
@@ -719,8 +733,10 @@ class MimeNode {
     }
     stream(outputStream, options, done) {
         const transferEncoding = this.getTransferEncoding();
-        let contentStream;
+        // the streams this node is reading from. A consumer that goes away mid-message destroys
-        let localStream;
+        // the output, and these are released with it instead of staying paused with a file or a
+        // socket open behind them
+        let activeStreams = [];
         // protect actual callback against multiple triggering
         let returned = false;
         const callback = (err) => {
@@ -728,13 +744,39 @@ class MimeNode {
                 return;
             }
             returned = true;
+            outputStream.removeListener('close', onOutputClose);
             done(err);
         };
+        function onOutputClose() {
+            for (const stream of activeStreams) {
+                stream.destroy();
+            }
+            return callback(abortedError());
+        }
+        // reads the streams into the output. The listener is only attached while the node reads
+        // something, a deeply nested tree would otherwise stack one per level on the output
+        const readInto = (...streams) => {
+            if (!activeStreams.length) {
+                outputStream.once('close', onOutputClose);
+            }
+            activeStreams = streams;
+        };
+        // stops here if the output was destroyed in the meantime
+        const aborted = () => {
+            if (outputStream.destroyed) {
+                callback(abortedError());
+                return true;
+            }
+            return false;
+        };
         // for multipart nodes, push child nodes
         // for content nodes end the stream
         const finalize = () => {
             let childId = 0;
             const processChildNode = () => {
+                if (aborted()) {
+                    return;
+                }
                 if (childId >= this.childNodes.length) {
                     outputStream.write('\r\n--' + this.boundary + '--\r\n');
                     return callback();
@@ -757,89 +799,80 @@ class MimeNode {
         };
         // pushes node content
         const sendContent = () => {
-            if (this.content) {
+            if (aborted()) {
-                if (Object.prototype.toString.call(this.content) === '[object Error]') {
+                return;
-                    // content is already errored
-                    return callback(this.content);
             }
-                if (typeof this.content.pipe === 'function') {
+            if (!this.content) {
-                    this.content.removeListener('error', this._contentErrorHandler);
+                return setImmediate(finalize);
-                    this._contentErrorHandler = err => callback(err);
-                    this.content.once('error', this._contentErrorHandler);
             }
             const createStream = () => {
+                if (aborted()) {
+                    return;
+                }
+                const contentError = this._takeStreamContent(this.content);
+                if (contentError) {
+                    return callback(contentError);
+                }
+                const localStream = this._getStream(this.content);
                 if (['quoted-printable', 'base64'].includes(transferEncoding)) {
-                        contentStream = new (transferEncoding === 'base64' ? base64 : qp).Encoder(options);
+                    const contentStream = transferEncoding === 'base64'
+                        ? new base64.Encoder(options)
+                        : // outside of text a lone CR or LF is data, encoding it keeps it from being
+                            // turned into a line break by a newline transform or the receiving side
+                            new qp.Encoder(Object.assign({}, options, { binary: !/^text\//i.test(this.contentType || '') }));
+                    readInto(localStream, contentStream);
                     contentStream.pipe(outputStream, {
                         end: false
                     });
-                        contentStream.once('end', finalize);
+                    // pipeline reports errors and tears both streams down. It calls back once the
-                        contentStream.once('error', err => callback(err));
+                    // encoder took all of its input, the encoded output may still be waiting to
-                        localStream = this._getStream(this.content);
+                    // be read, so the node is only done once the encoder's readable side ended
-                        localStream.pipe(contentStream);
+                    (0, node_stream_1.pipeline)(localStream, contentStream, err => err && callback(err));
+                    (0, node_stream_1.finished)(contentStream, { writable: false }, err => (err ? callback(err) : finalize()));
                 }
                 else {
                     // anything that is not QP or Base54 passes as-is
-                        localStream = this._getStream(this.content);
+                    readInto(localStream);
                     localStream.pipe(outputStream, {
                         end: false
                     });
-                        localStream.once('end', finalize);
+                    (0, node_stream_1.finished)(localStream, { writable: false }, err => (err ? callback(err) : finalize()));
                 }
-                    localStream.once('error', err => callback(err));
             };
             if (this.content._resolve) {
-                    const chunks = [];
-                    let chunklen = 0;
-                    let returned = false;
                 const sourceStream = this._getStream(this.content);
-                    sourceStream.on('error', err => {
+                readInto(sourceStream);
+                shared.resolveStream(sourceStream, (err, value) => {
+                    if (err) {
+                        return callback(err);
+                    }
                     if (returned) {
                         return;
                     }
-                        returned = true;
-                        callback(err);
-                    });
-                    sourceStream.on('readable', () => {
-                        let chunk;
-                        while ((chunk = sourceStream.read()) !== null) {
-                            chunks.push(chunk);
-                            chunklen += chunk.length;
-                        }
-                    });
-                    sourceStream.on('end', () => {
-                        if (returned) {
-                            return;
-                        }
-                        returned = true;
                     this.content._resolve = false;
-                        this.content._resolvedValue = Buffer.concat(chunks, chunklen);
+                    this.content._resolvedValue = value;
                     setImmediate(createStream);
                 });
             }
             else {
                 setImmediate(createStream);
             }
-                return;
-            }
-            return setImmediate(finalize);
         };
         if (this._raw) {
             setImmediate(() => {
-                if (Object.prototype.toString.call(this._raw) === '[object Error]') {
+                if (aborted()) {
-                    // content is already errored
+                    return;
-                    return callback(this._raw);
                 }
-                // remove default error handler (if set)
+                const rawError = this._takeStreamContent(this._raw);
-                if (typeof this._raw.pipe === 'function') {
+                if (rawError) {
-                    this._raw.removeListener('error', this._contentErrorHandler);
+                    return callback(rawError);
                 }
                 const raw = this._getStream(this._raw);
+                readInto(raw);
                 raw.pipe(outputStream, {
                     end: false
                 });
-                raw.on('error', err => outputStream.emit('error', err));
+                (0, node_stream_1.finished)(raw, { writable: false }, err => (err ? callback(err) : finalize()));
-                raw.on('end', finalize);
             });
         }
         else {
@@ -955,11 +988,7 @@ class MimeNode {
         if (this._raw && typeof this._raw.pipe === 'function') {
             // pre-stream handler. might be triggered if a stream is set as content
             // and 'error' fires before anything is done with this stream
-            this._contentErrorHandler = err => {
+            shared.recordStreamErrors(this._raw);
-                this._raw.removeListener('error', this._contentErrorHandler);
-                this._raw = err;
-            };
-            this._raw.once('error', this._contentErrorHandler);
         }
         return this;
     }
@@ -985,6 +1014,37 @@ class MimeNode {
         }
         return false;
     }
+    /**
+     * Destroys the content streams of this node and of every node below it
+     *
+     * @internal
+     */
+    _destroyContentStreams() {
+        shared.destroyStream(this.content);
+        shared.destroyStream(this._raw);
+        for (const child of this.childNodes) {
+            child._destroyContentStreams();
+        }
+    }
+    /**
+     * Checks that a content value can still be read before the node streams it. A stream is
+     * refused once it errored, ended or was destroyed: piping it would either never finish or
+     * produce an empty body without any error
+     *
+     * @param content Node content or raw value
+     * @returns The error to stop with, or null when the content can be read
+     * @internal
+     */
+    _takeStreamContent(content) {
+        if (Object.prototype.toString.call(content) === '[object Error]') {
+            return content;
+        }
+        if (!content || typeof content.pipe !== 'function' || content._resolvedValue) {
+            // the value of a resolved stream is read from the buffered copy
+            return null;
+        }
+        return shared.unreadableStreamError(content);
+    }
     /**
      * Detects and returns handle to a stream related with the content.
      *

node_modules/nodemailer/dist/cjs/nodemailer.js

@@ -50,10 +50,12 @@ const index_js_7 = __importDefault(require("./ses-transport/index.js"));
 const errors = __importStar(require("./errors.js"));
 const index_js_8 = __importDefault(require("./fetch/index.js"));
 const packageData = __importStar(require("./package-info.js"));
-const ETHEREAL_API = (process.env.ETHEREAL_API || 'https://api.nodemailer.com').replace(/\/+$/, '');
+// Read on use rather than at load, so that importing the module does not touch the
-const ETHEREAL_WEB = (process.env.ETHEREAL_WEB || 'https://ethereal.email').replace(/\/+$/, '');
+// environment (Deno refuses that without --allow-env, even for apps that never use Ethereal)
-const ETHEREAL_API_KEY = (process.env.ETHEREAL_API_KEY || '').replace(/\s*/g, '') || null;
+const etherealApi = () => (process.env.ETHEREAL_API || 'https://api.nodemailer.com').replace(/\/+$/, '');
-const ETHEREAL_CACHE = ['true', 'yes', 'y', '1'].includes((process.env.ETHEREAL_CACHE || 'yes').toString().trim().toLowerCase());
+const etherealWeb = () => (process.env.ETHEREAL_WEB || 'https://ethereal.email').replace(/\/+$/, '');
+const etherealApiKey = () => (process.env.ETHEREAL_API_KEY || '').replace(/\s*/g, '') || null;
+const etherealCache = () => ['true', 'yes', 'y', '1'].includes((process.env.ETHEREAL_CACHE || 'yes').toString().trim().toLowerCase());
 let testAccount = false;
 function createTransport(transporter, defaults) {
     let options;
@@ -114,11 +116,11 @@ function createTestAccount(apiUrl, callback) {
         });
     }
     const done = callback;
-    if (ETHEREAL_CACHE && testAccount) {
+    if (etherealCache() && testAccount) {
         setImmediate(() => done(null, testAccount));
         return promise;
     }
-    apiUrl = apiUrl || ETHEREAL_API;
+    apiUrl = apiUrl || etherealApi();
     const chunks = [];
     let chunklen = 0;
     const requestHeaders = {};
@@ -126,8 +128,9 @@ function createTestAccount(apiUrl, callback) {
         requestor: packageData.name,
         version: packageData.version
     };
-    if (ETHEREAL_API_KEY) {
+    const apiKey = etherealApiKey();
-        requestHeaders.Authorization = 'Bearer ' + ETHEREAL_API_KEY;
+    if (apiKey) {
+        requestHeaders.Authorization = 'Bearer ' + apiKey;
     }
     const fetchOptions = {
         contentType: 'application/json',
@@ -195,7 +198,7 @@ function getTestMessageUrl(info) {
         }
     }
     if (infoProps.has('STATUS') && infoProps.has('MSGID')) {
-        return ((testAccount && testAccount.web) || ETHEREAL_WEB) + '/message/' + infoProps.get('MSGID');
+        return ((testAccount && testAccount.web) || etherealWeb()) + '/message/' + infoProps.get('MSGID');
     }
     return false;
 }

node_modules/nodemailer/dist/cjs/package-info.d.ts

@@ -1,3 +1,3 @@
 export declare const name = "nodemailer";
-export declare const version = "10.0.15";
+export declare const version = "10.1.0";
 export declare const homepage = "https://nodemailer.com/";

node_modules/nodemailer/dist/cjs/package-info.js

@@ -3,5 +3,5 @@
 Object.defineProperty(exports, "__esModule", { value: true });
 exports.homepage = exports.version = exports.name = void 0;
 exports.name = 'nodemailer';
-exports.version = '10.0.15';
+exports.version = '10.1.0';
 exports.homepage = 'https://nodemailer.com/';

node_modules/nodemailer/dist/cjs/qp/index.d.ts

@@ -14,6 +14,8 @@ export declare function wrap(str: string, lineLength?: number): string;
 export interface QPEncoderOptions {
     /** Maximum length for lines, set to false to disable wrapping */
     lineLength?: number | false | undefined;
+    /** The input is binary data: a CR or LF that is not part of a CRLF pair is encoded */
+    binary?: boolean | undefined;
 }
 /** The name @types/nodemailer used for QPEncoderOptions */
 export type EncoderOptions = QPEncoderOptions;

node_modules/nodemailer/dist/cjs/qp/index.js

@@ -21,23 +21,52 @@ const QP_RANGES = [
     [0x20, 0x3c], // <SP>!"#$%&'()*+,-./0123456789:;
     [0x3e, 0x7e] // >?@ABCDEFGHIJKLMNOPQRSTUVWXYZ[\]^_`abcdefghijklmnopqrstuvwxyz{|}
 ];
-function encode(buffer) {
+// 1 for every byte value that is written as is, see QP_RANGES
-    if (typeof buffer === 'string') {
+const QP_LITERAL = new Uint8Array(256);
-        buffer = Buffer.from(buffer, 'utf-8');
+for (let i = 0; i < 256; i++) {
+    QP_LITERAL[i] = checkRanges(i, QP_RANGES) ? 1 : 0;
 }
-    let result = '';
+const HEX_DIGITS = Buffer.from('0123456789ABCDEF', 'latin1');
-    let ord;
+const isWhitespace = (c) => c === 0x20 || c === 0x09;
-    for (let i = 0, len = buffer.length; i < len; i++) {
+function encode(buffer) {
-        ord = buffer[i];
+    return encodeBytes(typeof buffer === 'string' ? Buffer.from(buffer, 'utf-8') : buffer);
+}
+/**
+ * Encodes bytes that may be followed by more input
+ *
+ * @param buffer Bytes to encode
+ * @param [next] The byte that follows the buffer, whitespace before it is kept literal unless it
+ *        is a line break. Without it the buffer ends the input and its trailing whitespace is encoded
+ * @param [binary] Keep only CRLF pairs literal. A lone CR or LF is data, not a line break, and
+ *        anything that rewrites line endings on the way would change it
+ * @param [previous] The byte before the buffer, for a buffer that starts with LF
+ * @returns Quoted-Printable encoded string
+ */
+function encodeBytes(buffer, next, binary, previous) {
+    const len = buffer.length;
+    // every byte takes three characters at most
+    const output = Buffer.allocUnsafe(len * 3);
+    let pos = 0;
+    for (let i = 0; i < len; i++) {
+        const ord = buffer[i];
+        const following = i + 1 < len ? buffer[i + 1] : next;
+        const lineBreakByte = binary && (ord === 0x0d || ord === 0x0a)
+            ? ord === 0x0d
+                ? following === 0x0a
+                : (i > 0 ? buffer[i - 1] : previous) === 0x0d
+            : true;
         // if the char is in allowed range, then keep as is, unless it is a WS in the end of a line
-        if (checkRanges(ord, QP_RANGES) &&
+        if (QP_LITERAL[ord] &&
-            !((ord === 0x20 || ord === 0x09) && (i === len - 1 || buffer[i + 1] === 0x0a || buffer[i + 1] === 0x0d))) {
+            lineBreakByte &&
-            result += String.fromCharCode(ord);
+            !(isWhitespace(ord) && (following === undefined || following === 0x0a || following === 0x0d))) {
+            output[pos++] = ord;
             continue;
         }
-        result += '=' + (ord < 0x10 ? '0' : '') + ord.toString(16).toUpperCase();
+        output[pos++] = 0x3d; // =
+        output[pos++] = HEX_DIGITS[Math.floor(ord / 16)];
+        output[pos++] = HEX_DIGITS[ord % 16];
     }
-    return result;
+    return output.toString('latin1', 0, pos);
 }
 /**
  * Adds soft line breaks to a Quoted-Printable string
@@ -148,6 +177,10 @@ function checkRanges(nr, ranges) {
     }
     return false;
 }
+// Input is encoded and wrapped this many bytes at a time. wrap() works on strings, and a large
+// chunk handed over at once, such as a whole Buffer attachment, would be held several times over
+// as intermediate strings
+const ENCODE_SLICE_SIZE = 64 * 1024;
 /**
  * Creates a transform stream for encoding data to Quoted-Printable encoding
  *
@@ -163,45 +196,82 @@ class Encoder extends node_stream_1.Transform {
             this.options.lineLength = this.options.lineLength || 76;
         }
         this._curLine = '';
+        this._remainingBytes = false;
+        this._lastByte = undefined;
         this.inputBytes = 0;
         this.outputBytes = 0;
     }
     /** @internal */
     _transform(chunk, encoding, done) {
-        let qp;
+        let buf = encoding !== 'buffer' ? Buffer.from(chunk, encoding) : chunk;
-        if (encoding !== 'buffer') {
+        if (!buf || !buf.length) {
-            chunk = Buffer.from(chunk, encoding);
-        }
-        if (!chunk || !chunk.length) {
             return done();
         }
-        this.inputBytes += chunk.length;
+        this.inputBytes += buf.length;
-        if (this.options.lineLength) {
+        if (this._remainingBytes) {
-            qp = this._curLine + encode(chunk);
+            buf = Buffer.concat([this._remainingBytes, buf], this._remainingBytes.length + buf.length);
-            qp = wrap(qp, this.options.lineLength);
+            this._remainingBytes = false;
-            qp = qp.replace(/(^|\n)([^\n]*)$/, (match, lineBreak, lastLine) => {
-                this._curLine = lastLine;
-                return lineBreak;
-            });
-            if (qp) {
-                this.outputBytes += qp.length;
-                this.push(qp);
         }
+        // Whitespace is encoded when it ends a line, and the end of the input counts as one. Hold
+        // back the whitespace a chunk ends with until it is known what follows it, so the output
+        // does not depend on where the input was split
+        let end = buf.length;
+        // a binary CR can only be written once it is known whether LF follows
+        while (end > 0 && (isWhitespace(buf[end - 1]) || (this.options.binary && buf[end - 1] === 0x0d))) {
+            end--;
         }
-        else {
+        if (buf.length - end <= ENCODE_SLICE_SIZE) {
-            qp = encode(chunk);
+            this._remainingBytes = end < buf.length ? Buffer.from(buf.subarray(end)) : false;
-            this.outputBytes += qp.length;
+            buf = buf.subarray(0, end);
-            this.push(qp, 'ascii');
         }
+        this._encodeSlices(buf);
         done();
     }
     /** @internal */
     _flush(done) {
+        if (this._remainingBytes) {
+            this._encodeSlices(this._remainingBytes);
+            this._remainingBytes = false;
+        }
         if (this._curLine) {
             this.outputBytes += this._curLine.length;
             this.push(this._curLine, 'ascii');
+            this._curLine = '';
         }
         done();
     }
+    /**
+     * Encodes the input in slices of ENCODE_SLICE_SIZE bytes. Each slice is told the byte that
+     * follows it, so a slice that ends in whitespace is encoded as if it was not split
+     *
+     * @internal
+     */
+    _encodeSlices(buf) {
+        for (let start = 0; start < buf.length; start += ENCODE_SLICE_SIZE) {
+            const end = Math.min(start + ENCODE_SLICE_SIZE, buf.length);
+            this._encodeSlice(buf.subarray(start, end), end < buf.length ? buf[end] : undefined);
+            this._lastByte = buf[end - 1];
+        }
+    }
+    /** @internal */
+    _encodeSlice(buf, next) {
+        let qp;
+        if (this.options.lineLength) {
+            qp = wrap(this._curLine + encodeBytes(buf, next, this.options.binary, this._lastByte), this.options.lineLength);
+            // the last line is kept until it is known whether it needs a soft break
+            const lastLF = qp.lastIndexOf('\n');
+            this._curLine = qp.substring(lastLF + 1);
+            qp = qp.substring(0, lastLF + 1);
+            if (qp) {
+                this.outputBytes += qp.length;
+                this.push(qp, 'ascii');
+            }
+        }
+        else {
+            qp = encodeBytes(buf, next, this.options.binary, this._lastByte);
+            this.outputBytes += qp.length;
+            this.push(qp, 'ascii');
+        }
+    }
 }
 exports.Encoder = Encoder;

node_modules/nodemailer/dist/cjs/sendmail-transport/index.js

@@ -37,11 +37,14 @@ var __importDefault = (this && this.__importDefault) || function (mod) {
 };
 Object.defineProperty(exports, "__esModule", { value: true });
 const node_child_process_1 = require("node:child_process");
+const node_stream_1 = require("node:stream");
 const packageData = __importStar(require("../package-info.js"));
 const shared = __importStar(require("../shared/index.js"));
 const errors = __importStar(require("../errors.js"));
 const le_windows_js_1 = __importDefault(require("../mime-node/le-windows.js"));
 const le_unix_js_1 = __importDefault(require("../mime-node/le-unix.js"));
+// how long an stdin error waits for the exit code of the process before it is reported
+const STDIN_ERROR_EXIT_WAIT = 1000;
 /**
  * Generates a Transport object for Sendmail
  *
@@ -139,37 +142,75 @@ class SendmailTransport {
             return callback(E);
         }
         if (sendmail) {
+            let stream;
+            // ended once the whole message was handed to stdin
+            const messageWritten = () => !!stream && stream.readableEnded;
+            // an EPIPE says less than the exit code that usually follows it, so it is only
+            // reported when the process exits without one
+            let stdinError = null;
+            // releases whatever the message is still being read from
+            const release = () => {
+                if (stream && !messageWritten()) {
+                    stream.destroy();
+                }
+            };
+            const fail = (err) => {
+                release();
+                callback(err);
+            };
             sendmail.on('error', err => {
                 this.logger.error({
                     err,
                     tnx: 'spawn',
                     messageId
                 }, 'Error occurred when sending message %s. %s', messageId, err.message);
-                callback(err);
+                fail(err);
             });
-            sendmail.once('exit', code => {
+            // 'close' follows 'exit' with the same arguments, it is only listened to in case the
-                if (!code) {
+            // process ends without an 'exit' event
+            const onExit = (code, signal) => {
+                let err = null;
+                if (code) {
+                    err = new Error(code === 127 ? 'Sendmail command not found, process exited with code ' + code : 'Sendmail exited with code ' + code);
+                }
+                else if (signal) {
+                    err = new Error('Sendmail was terminated by ' + signal);
+                }
+                else if (!messageWritten()) {
+                    // exiting with 0 before the message was written does not mean it was queued
+                    err = new Error('Sendmail exited before the message was written');
+                }
+                else if (stdinError) {
+                    err = stdinError;
+                }
+                if (!err) {
                     return callback();
                 }
-                const err = new Error(code === 127 ? 'Sendmail command not found, process exited with code ' + code : 'Sendmail exited with code ' + code);
+                err.code = err.code || errors.ESENDMAIL;
-                err.code = errors.ESENDMAIL;
                 this.logger.error({
                     err,
                     tnx: 'stdin',
                     messageId
                 }, 'Error sending message %s to sendmail. %s', messageId, err.message);
-                callback(err);
+                fail(err);
-            });
+            };
-            // the close listener is handed the exit code as its first argument, so a non-zero
+            sendmail.once('exit', onExit);
-            // code reaching it before the exit listener did counts as the error value
+            sendmail.once('close', onExit);
-            sendmail.once('close', callback);
             sendmail.stdin.on('error', err => {
                 this.logger.error({
                     err,
                     tnx: 'stdin',
                     messageId
                 }, 'Error occurred when piping message %s to sendmail. %s', messageId, err.message);
-                callback(err);
+                if (stdinError) {
+                    return;
+                }
+                stdinError = err;
+                release();
+                // a process that closed its stdin normally exits right after, with a code that
+                // tells more than the EPIPE. Report the EPIPE if it does not
+                const exitTimer = setTimeout(() => fail(err), STDIN_ERROR_EXIT_WAIT);
+                sendmail.once('exit', () => clearTimeout(exitTimer));
             });
             const recipients = [].concat(envelope.to || []);
             if (recipients.length > 3) {
@@ -180,12 +221,11 @@ class SendmailTransport {
                 messageId
             }, 'Sending message %s to <%s>', messageId, recipients.join(', '));
             const sourceStream = mail.message.createReadStream();
-            let stream = sourceStream;
+            stream = sourceStream;
             if (this.options.newline) {
                 // apply the transport-level line ending transform; the message-level
                 // `newline` option is handled by MimeNode in createReadStream()
-                stream = sourceStream.pipe(this.winbreak ? new le_windows_js_1.default() : new le_unix_js_1.default());
+                stream = (0, node_stream_1.pipeline)(sourceStream, this.winbreak ? new le_windows_js_1.default() : new le_unix_js_1.default(), () => false);
-                sourceStream.once('error', err => stream.emit('error', err));
             }
             stream.once('error', err => {
                 this.logger.error({

node_modules/nodemailer/dist/cjs/shared/index.d.ts

@@ -1,6 +1,7 @@
+import type { NodemailerError } from '../errors.js';
 import { isProtoKey, copyOwnKeys } from './objects.js';
 import os from 'node:os';
-import type { Readable } from 'node:stream';
+import { type Readable } from 'node:stream';
 import type { OutgoingHttpHeaders } from 'node:http';
 export { isProtoKey, copyOwnKeys };
 /**
@@ -258,3 +259,33 @@ export declare const assign: (...args: ({
     [key: string]: any;
 };
 export declare const encodeXText: (str: string) => string;
+/**
+ * Keeps the first error a content stream emits before it is read, so the error is reported
+ * when the stream is read instead of being thrown as unhandled. The listener stays attached
+ * for good, a stream that emits 'error' more than once never throws the later ones either
+ *
+ * @param stream Readable stream
+ */
+export declare function recordStreamErrors(stream: Readable): void;
+/**
+ * Destroys a value if it is a readable stream that was not destroyed yet
+ *
+ * @param value Any content value
+ */
+export declare function destroyStream(value: unknown): void;
+/**
+ * Tells why a stream can not be read from start to end anymore. A stream that ended or was
+ * destroyed before anyone read it would never emit 'end' to a new reader, or, when piped, would
+ * end the destination right away and turn into an empty value without any error
+ *
+ * @param stream Readable stream
+ * @returns The error the stream failed with, an ESTREAM error, or null when it can be read
+ */
+export declare function unreadableStreamError(stream: Readable): NodemailerError | null;
+/**
+ * Streams a stream value into a Buffer
+ *
+ * @param stream Readable stream
+ * @param callback Callback function with (err, value)
+ */
+export declare function resolveStream(stream: Readable, callback: (err: Error | null, value?: Buffer) => void): void;

node_modules/nodemailer/dist/cjs/shared/index.js

@@ -37,8 +37,12 @@ var __importDefault = (this && this.__importDefault) || function (mod) {
     return (mod && mod.__esModule) ? mod : { "default": mod };
 };
 Object.defineProperty(exports, "__esModule", { value: true });
-exports.encodeXText = exports.assign = exports.parseDataURI = exports.callbackPromise = exports.getLogger = exports._logFunc = exports.parseConnectionUrl = exports.resolveHostname = exports.dnsCache = exports.networkInterfaces = exports._resetCacheCleanup = exports._lastCacheCleanup = exports.copyOwnKeys = exports.isProtoKey = void 0;
+exports.encodeXText = exports.assign = exports.parseDataURI = exports.callbackPromise = exports.getLogger = exports._logFunc = exports.parseConnectionUrl = exports.resolveHostname = exports.dnsCache = exports._readNetworkInterfaces = exports.networkInterfaces = exports._resetCacheCleanup = exports._lastCacheCleanup = exports.copyOwnKeys = exports.isProtoKey = void 0;
 exports.resolveContent = resolveContent;
+exports.recordStreamErrors = recordStreamErrors;
+exports.destroyStream = destroyStream;
+exports.unreadableStreamError = unreadableStreamError;
+exports.resolveStream = resolveStream;
 const urllib = __importStar(require("./url.js"));
 const node_util_1 = __importDefault(require("node:util"));
 const node_fs_1 = __importDefault(require("node:fs"));
@@ -50,6 +54,7 @@ Object.defineProperty(exports, "copyOwnKeys", { enumerable: true, get: function
 const node_dns_1 = __importDefault(require("node:dns"));
 const node_net_1 = __importDefault(require("node:net"));
 const node_os_1 = __importDefault(require("node:os"));
+const node_stream_1 = require("node:stream");
 const DNS_TTL = 5 * 60 * 1000;
 const CACHE_CLEANUP_INTERVAL = 30 * 1000; // Minimum 30 seconds between cleanups
 const MAX_CACHE_SIZE = 1000; // Maximum number of entries in cache
@@ -62,14 +67,25 @@ const _resetCacheCleanup = () => {
     lastCacheCleanup = 0;
 };
 exports._resetCacheCleanup = _resetCacheCleanup;
+let networkInterfacesRead = false;
+// Read on first use rather than at load, so that importing the module does not ask for
+// the interface table (Deno prompts for --allow-sys on it)
+/** @internal */
+const _readNetworkInterfaces = () => {
+    if (!networkInterfacesRead) {
+        networkInterfacesRead = true;
         try {
             exports.networkInterfaces = node_os_1.default.networkInterfaces();
         }
         catch (_err) {
             // fails on some systems
         }
+    }
+    return exports.networkInterfaces;
+};
+exports._readNetworkInterfaces = _readNetworkInterfaces;
 const isFamilySupported = (family, allowInternal) => {
-    const addresses = Object.values(exports.networkInterfaces || {}).flat();
+    const addresses = Object.values((0, exports._readNetworkInterfaces)() || {}).flat();
     if (!addresses.length) {
         // hope for the best. Runtimes without an interface table (Cloudflare
         // Workers) report an empty object rather than throwing
@@ -80,7 +96,8 @@ const isFamilySupported = (family, allowInternal) => {
 const resolve = (family, hostname, options, callback) => {
     options = options || {};
     if (!isFamilySupported(family, options.allowInternalNetworkInterfaces)) {
-        return callback(null, []);
+        callback(null, []);
+        return null;
     }
     const dnsResolver = node_dns_1.default.Resolver ? new node_dns_1.default.Resolver(options) : node_dns_1.default;
     dnsResolver['resolve' + family](hostname, (err, addresses) => {
@@ -99,6 +116,7 @@ const resolve = (family, hostname, options, callback) => {
         }
         return callback(null, Array.isArray(addresses) ? addresses : [].concat(addresses || []));
     });
+    return node_dns_1.default.Resolver ? dnsResolver : null;
 };
 exports.dnsCache = new Map();
 const formatDNSValue = (value, extra) => {
@@ -162,24 +180,59 @@ const resolveHostname = (options, callback) => {
             }));
         }
     }
-    // Resolve both IPv4 and IPv6 addresses for fallback support
+    // The timeout limits the lookup as a whole. It is also handed to the resolver, but there
+    // it applies to every query attempt on its own, and the resolver retries a few times
+    let responded = false;
+    let deadline;
+    const respond = (err, result) => {
+        if (responded) {
+            return;
+        }
+        responded = true;
+        clearTimeout(deadline);
+        callback(err, result);
+    };
+    // a stale cached value is still better than no value at all
+    const respondCached = (error) => {
+        if (!cached) {
+            return false;
+        }
+        exports.dnsCache.set(host, {
+            value: cached.value,
+            expires: Date.now() + (options.dnsTtl || DNS_TTL)
+        });
+        respond(null, formatDNSValue(cached.value, {
+            servername,
+            cached: true,
+            error
+        }));
+        return true;
+    };
+    const resolvers = [];
+    const timeout = Number(options.timeout) || 0;
+    if (timeout > 0) {
+        deadline = setTimeout(() => {
+            for (const resolver of resolvers) {
+                if (typeof resolver.cancel === 'function') {
+                    resolver.cancel();
+                }
+            }
+            const err = new Error('DNS lookup for ' + host + ' timed out');
+            err.code = node_dns_1.default.TIMEOUT;
+            if (!respondCached(err)) {
+                respond(err);
+            }
+        }, timeout);
+    }
+    // Resolve both IPv4 and IPv6 addresses for fallback support, at the same time
     let ipv4Addresses = [];
     let ipv6Addresses = [];
     let ipv4Error = null;
     let ipv6Error = null;
-    resolve(4, options.host, options, (err, addresses) => {
+    let pending = 2;
-        if (err) {
+    const onResolved = () => {
-            ipv4Error = err;
+        if (--pending || responded) {
-        }
+            return;
-        else {
-            ipv4Addresses = addresses || [];
-        }
-        resolve(6, host, options, (err, addresses) => {
-            if (err) {
-                ipv6Error = err;
-            }
-            else {
-                ipv6Addresses = addresses || [];
         }
         // Combine addresses: IPv4 first, then IPv6
         const allAddresses = ipv4Addresses.concat(ipv6Addresses);
@@ -191,41 +244,23 @@ const resolveHostname = (options, callback) => {
                 value,
                 expires: Date.now() + (options.dnsTtl || DNS_TTL)
             });
-                return callback(null, formatDNSValue(value, {
+            return respond(null, formatDNSValue(value, {
                 servername,
                 cached: false
             }));
         }
         // No addresses from resolve4/resolve6, try dns.lookup as fallback
-            if (ipv4Error && ipv6Error) {
+        if (ipv4Error && ipv6Error && respondCached(ipv4Error)) {
             // Both resolvers had errors
-                if (cached) {
+            return;
-                    exports.dnsCache.set(host, {
-                        value: cached.value,
-                        expires: Date.now() + (options.dnsTtl || DNS_TTL)
-                    });
-                    return callback(null, formatDNSValue(cached.value, {
-                        servername,
-                        cached: true,
-                        error: ipv4Error
-                    }));
-                }
         }
         try {
             node_dns_1.default.lookup(host, { all: true }, (err, addresses) => {
                 if (err) {
-                        if (cached) {
+                    if (respondCached(err)) {
-                            exports.dnsCache.set(host, {
+                        return;
-                                value: cached.value,
-                                expires: Date.now() + (options.dnsTtl || DNS_TTL)
-                            });
-                            return callback(null, formatDNSValue(cached.value, {
-                                servername,
-                                cached: true,
-                                error: err
-                            }));
                     }
-                        return callback(err);
+                    return respond(err);
                 }
                 // Get all supported addresses from dns.lookup
                 const supportedAddresses = addresses
@@ -237,7 +272,7 @@ const resolveHostname = (options, callback) => {
                 }
                 if (!supportedAddresses.length && cached) {
                     // nothing was found, fallback to cached value
-                        return callback(null, formatDNSValue(cached.value, {
+                    return respond(null, formatDNSValue(cached.value, {
                         servername,
                         cached: true
                     }));
@@ -249,28 +284,35 @@ const resolveHostname = (options, callback) => {
                     value,
                     expires: Date.now() + (options.dnsTtl || DNS_TTL)
                 });
-                    return callback(null, formatDNSValue(value, {
+                return respond(null, formatDNSValue(value, {
                     servername,
                     cached: false
                 }));
             });
         }
         catch (lookupErr) {
-                if (cached) {
+            if (respondCached(lookupErr)) {
-                    exports.dnsCache.set(host, {
+                return;
-                        value: cached.value,
-                        expires: Date.now() + (options.dnsTtl || DNS_TTL)
-                    });
-                    return callback(null, formatDNSValue(cached.value, {
-                        servername,
-                        cached: true,
-                        error: lookupErr
-                    }));
             }
-                return callback(ipv4Error || ipv6Error || lookupErr);
+            return respond(ipv4Error || ipv6Error || lookupErr);
         }
+    };
+    for (const family of [4, 6]) {
+        const resolver = resolve(family, host, options, (err, addresses) => {
+            if (family === 4) {
+                ipv4Error = err;
+                ipv4Addresses = addresses || [];
+            }
+            else {
+                ipv6Error = err;
+                ipv6Addresses = addresses || [];
+            }
+            onResolved();
         });
-    });
+        if (resolver) {
+            resolvers.push(resolver);
+        }
+    }
 };
 exports.resolveHostname = resolveHostname;
 /**
@@ -597,6 +639,53 @@ const encodeXText = (str) => {
     return result;
 };
 exports.encodeXText = encodeXText;
+// The first error a stream emitted, see recordStreamErrors
+const streamErrors = new WeakMap();
+/**
+ * Keeps the first error a content stream emits before it is read, so the error is reported
+ * when the stream is read instead of being thrown as unhandled. The listener stays attached
+ * for good, a stream that emits 'error' more than once never throws the later ones either
+ *
+ * @param stream Readable stream
+ */
+function recordStreamErrors(stream) {
+    stream.on('error', err => {
+        if (!streamErrors.has(stream)) {
+            streamErrors.set(stream, err);
+        }
+    });
+}
+/**
+ * Destroys a value if it is a readable stream that was not destroyed yet
+ *
+ * @param value Any content value
+ */
+function destroyStream(value) {
+    const stream = value;
+    if (stream && typeof stream.pipe === 'function' && typeof stream.destroy === 'function' && !stream.destroyed) {
+        stream.destroy();
+    }
+}
+/**
+ * Tells why a stream can not be read from start to end anymore. A stream that ended or was
+ * destroyed before anyone read it would never emit 'end' to a new reader, or, when piped, would
+ * end the destination right away and turn into an empty value without any error
+ *
+ * @param stream Readable stream
+ * @returns The error the stream failed with, an ESTREAM error, or null when it can be read
+ */
+function unreadableStreamError(stream) {
+    const err = streamErrors.get(stream) || stream.errored;
+    if (err) {
+        return err;
+    }
+    if (stream.readableEnded || stream.destroyed) {
+        const unreadable = new Error('Content stream was already read or destroyed');
+        unreadable.code = errors.ESTREAM;
+        return unreadable;
+    }
+    return null;
+}
 /**
  * Streams a stream value into a Buffer
  *
@@ -605,35 +694,43 @@ exports.encodeXText = encodeXText;
  */
 function resolveStream(stream, callback) {
     let responded = false;
+    const respond = (err, value) => {
+        if (responded) {
+            return;
+        }
+        responded = true;
+        callback(err, value);
+    };
+    const unreadable = unreadableStreamError(stream);
+    if (unreadable) {
+        // absorbs a later 'error' from the stream, there is nobody left to report it to
+        stream.on('error', () => false);
+        setImmediate(() => respond(unreadable));
+        return;
+    }
     const chunks = [];
     let chunklen = 0;
-    stream.on('error', err => {
+    stream.on('data', (chunk) => {
-        if (responded) {
+        if (typeof chunk === 'string') {
-            return;
+            chunk = Buffer.from(chunk);
         }
-        responded = true;
-        callback(err);
-    });
-    stream.on('readable', () => {
-        let chunk;
-        while ((chunk = stream.read()) !== null) {
         chunks.push(chunk);
         chunklen += chunk.length;
-        }
     });
-    stream.on('end', () => {
+    // finished() also reports a stream that is destroyed before 'end', which would otherwise
-        if (responded) {
+    // leave the callback waiting forever
-            return;
+    (0, node_stream_1.finished)(stream, { writable: false }, err => {
+        if (err) {
+            return respond(err);
         }
-        responded = true;
         let value;
         try {
             value = Buffer.concat(chunks, chunklen);
         }
         catch (E) {
-            return callback(E);
+            return respond(E);
         }
-        callback(null, value);
+        respond(null, value);
     });
 }
 /**

node_modules/nodemailer/dist/cjs/smtp-connection/http-proxy-client.d.ts

@@ -9,6 +9,8 @@ import type { Callback } from '../errors.js';
 export interface HttpProxyClientOptions {
     /** Set to false to accept a proxy certificate that fails validation (e.g. self-signed) */
     rejectUnauthorized?: boolean | undefined;
+    /** Time in milliseconds the CONNECT handshake may take, defaults to httpProxyClient.timeout or 30 seconds */
+    timeout?: number | undefined;
 }
 /**
  * Receives the proxied socket once the CONNECT handshake has succeeded, or the error that prevented it
@@ -38,7 +40,7 @@ declare function httpProxyClient(proxyUrl: string, destinationPort: number | str
  */
 declare function httpProxyClient(proxyUrl: string, destinationPort: number | string, destinationHost: string, tlsOptions: HttpProxyClientOptions | undefined, callback: HttpProxyClientCallback): void;
 /**
- * Socket timeout in milliseconds while the CONNECT handshake is in progress, defaults to 30 seconds.
+ * Time in milliseconds the CONNECT handshake may take when the call does not set one, defaults to 30 seconds.
  * Settable on the function itself, the same way the CommonJS module exposed it.
  */
 declare namespace httpProxyClient {

node_modules/nodemailer/dist/cjs/smtp-connection/http-proxy-client.js

@@ -46,6 +46,8 @@ const errors = __importStar(require("../errors.js"));
 // Cap the CONNECT response we buffer before the header terminator, so a proxy that
 // never sends \r\n\r\n cannot grow memory unboundedly before the socket times out.
 const MAX_RESPONSE_HEADER_BYTES = 64 * 1024;
+// URL hostnames keep the brackets around an IPv6 literal, socket options and net.isIPv6 take it without
+const unbracket = (host) => typeof host === 'string' && host.startsWith('[') && host.endsWith(']') ? host.slice(1, -1) : host;
 function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions, callback) {
     if (typeof tlsOptions === 'function') {
         callback = tlsOptions;
@@ -65,6 +67,8 @@ function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions,
         return;
     }
     const proxy = urllib.parse(proxyUrl);
+    // the CONNECT request line and the Host header take an IPv6 destination in brackets
+    const authority = (node_net_1.default.isIPv6(unbracket(destinationHost)) ? '[' + unbracket(destinationHost) + ']' : destinationHost) + ':' + destinationPort;
     const connectOptions = {
         host: proxy.hostname,
         port: Number(proxy.port) ? Number(proxy.port) : proxy.protocol === 'https:' ? 443 : 80
@@ -80,15 +84,27 @@ function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions,
     else {
         connect = node_net_1.default.connect.bind(node_net_1.default);
     }
+    // The handshake is bounded as a whole, a proxy that keeps sending a byte now and then can
+    // not hold the connection open past it
+    const timeout = Number(tlsOptions.timeout) || httpProxyClient.timeout || 30 * 1000;
     let socket;
-    // Error harness for initial connection. Once connection is established, the responsibility
+    // Single settlement path for the handshake: every temporary listener and the timer are
-    // to handle errors is passed to whoever uses this socket
+    // dropped exactly once. Once the tunnel is up, the responsibility to handle errors is passed
+    // to whoever uses this socket
     let finished = false;
-    const tempSocketErr = (err) => {
+    let timer;
+    const cleanup = () => {
+        clearTimeout(timer);
+        socket.removeListener('data', onSocketData);
+        socket.removeListener('error', fail);
+        socket.removeListener('close', onEarlyClose);
+    };
+    function fail(err) {
         if (finished) {
             return;
         }
         finished = true;
+        cleanup();
         try {
             socket.destroy();
         }
@@ -96,44 +112,19 @@ function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions,
             // ignore
         }
         done(err);
-    };
-    const timeoutErr = () => {
-        const err = new Error('Proxy socket timed out');
-        err.code = 'ETIMEDOUT';
-        tempSocketErr(err);
-    };
-    socket = connect(connectOptions, () => {
-        if (finished) {
-            return;
     }
-        const reqHeaders = {
+    function onEarlyClose() {
-            Host: destinationHost + ':' + destinationPort,
+        const err = new Error('Proxy closed the connection before the tunnel was established');
-            Connection: 'close'
+        err.code = errors.EPROXY;
-        };
+        fail(err);
-        if (proxy.auth) {
-            reqHeaders['Proxy-Authorization'] = 'Basic ' + Buffer.from(proxy.auth).toString('base64');
     }
-        socket.write(
-        // HTTP method
-        'CONNECT ' +
-            destinationHost +
-            ':' +
-            destinationPort +
-            ' HTTP/1.1\r\n' +
-            // HTTP request headers
-            Object.keys(reqHeaders)
-                .map(key => key + ': ' + reqHeaders[key])
-                .join('\r\n') +
-            // End request
-            '\r\n\r\n');
     // The response is collected as chunks and only the bytes that just arrived, together
     // with the three before them, are searched for the end of the headers. Appending to a
     // string and searching all of it again re-read the whole response on every chunk.
     const chunks = [];
     let received = 0;
     let tail = '';
-        const onSocketData = (chunk) => {
+    function onSocketData(chunk) {
-            let match;
         if (finished) {
             return;
         }
@@ -142,47 +133,76 @@ function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions,
         chunks.push(chunk);
         received += chunk.length;
         tail = window.slice(-3);
-            if (windowEnd >= 0) {
+        if (windowEnd < 0) {
+            if (received > MAX_RESPONSE_HEADER_BYTES) {
+                const err = new Error('Proxy response headers too large');
+                err.code = errors.EPROXY;
+                fail(err);
+            }
+            return;
+        }
+        // Stop reading before anything is put back. A socket that keeps flowing would emit the
+        // bytes after the headers, a greeting the proxy sent together with its own response,
+        // before the next owner of the socket has a listener for them
         socket.removeListener('data', onSocketData);
+        socket.pause();
         const headerEnd = received - window.length + windowEnd;
-                const response = Buffer.concat(chunks, received).toString('binary');
+        const response = Buffer.concat(chunks, received);
-                const headers = response.substr(0, headerEnd);
+        if (response.length > headerEnd + 4) {
-                const remainder = response.substr(headerEnd + 4);
+            socket.unshift(response.subarray(headerEnd + 4));
-                if (remainder) {
+        }
-                    socket.unshift(Buffer.from(remainder, 'binary'));
+        // check response code
+        const match = response.toString('binary', 0, headerEnd).match(/^HTTP\/\d+\.\d+ (\d+)/i);
+        if (!match || (match[1] || '').charAt(0) !== '2') {
+            const err = new Error('Invalid response from proxy' + ((match && ': ' + match[1]) || ''));
+            err.code = errors.EPROXY;
+            return fail(err);
         }
         // proxy connection is now established
         finished = true;
-                // check response code
+        cleanup();
-                match = headers.match(/^HTTP\/\d+\.\d+ (\d+)/i);
+        // A fresh socket starts flowing once something listens for 'data', a paused one would
-                if (!match || (match[1] || '').charAt(0) !== '2') {
+        // not. Keep that behaviour for the next owner of the socket
-                    try {
+        const resumeOnData = (event) => {
-                        socket.destroy();
+            if (event === 'data') {
-                    }
+                socket.removeListener('newListener', resumeOnData);
-                    catch (_E) {
+                socket.resume();
-                        // ignore
-                    }
-                    const err = new Error('Invalid response from proxy' + ((match && ': ' + match[1]) || ''));
-                    err.code = errors.EPROXY;
-                    return done(err);
-                }
-                socket.removeListener('error', tempSocketErr);
-                socket.removeListener('timeout', timeoutErr);
-                socket.setTimeout(0);
-                return done(null, socket);
-            }
-            if (received > MAX_RESPONSE_HEADER_BYTES) {
-                socket.removeListener('data', onSocketData);
-                const err = new Error('Proxy response headers too large');
-                err.code = errors.EPROXY;
-                return tempSocketErr(err);
             }
         };
+        socket.on('newListener', resumeOnData);
+        return done(null, socket);
+    }
+    socket = connect(connectOptions, () => {
+        if (finished) {
+            return;
+        }
+        const reqHeaders = {
+            Host: authority,
+            Connection: 'close'
+        };
+        if (proxy.auth) {
+            reqHeaders['Proxy-Authorization'] = 'Basic ' + Buffer.from(proxy.auth).toString('base64');
+        }
+        socket.write(
+        // HTTP method
+        'CONNECT ' +
+            authority +
+            ' HTTP/1.1\r\n' +
+            // HTTP request headers
+            Object.keys(reqHeaders)
+                .map(key => key + ': ' + reqHeaders[key])
+                .join('\r\n') +
+            // End request
+            '\r\n\r\n');
         socket.on('data', onSocketData);
     });
-    socket.setTimeout(httpProxyClient.timeout || 30 * 1000);
+    timer = setTimeout(() => {
-    socket.on('timeout', timeoutErr);
+        const err = new Error('Proxy socket timed out');
-    socket.once('error', tempSocketErr);
+        err.code = errors.ETIMEDOUT;
+        fail(err);
+    }, timeout);
+    socket.once('error', fail);
+    socket.once('close', onEarlyClose);
 }
 exports.default = httpProxyClient;
 module.exports = exports.default;

node_modules/nodemailer/dist/cjs/smtp-connection/index.d.ts

@@ -3,7 +3,7 @@ import net from 'node:net';
 import tls from 'node:tls';
 import { type Readable } from 'node:stream';
 import * as shared from '../shared/index.js';
-import type { Callback, NodemailerError } from '../errors.js';
+import { type Callback, type NodemailerError } from '../errors.js';
 import type XOAuth2 from '../xoauth2/index.js';
 import type { XOAuth2Options } from '../xoauth2/index.js';
 /**
@@ -275,6 +275,12 @@ export interface SMTPConnectionConnectOptions extends tls.ConnectionOptions {
     allowInternalNetworkInterfaces?: boolean | undefined;
     /** DNS lookup timeout in ms */
     timeout?: number | undefined;
+    /** Try the resolved addresses in turn, see net.connect */
+    autoSelectFamily?: boolean | undefined;
+    /** Time in ms an address gets before the next one is tried, see net.connect */
+    autoSelectFamilyAttemptTimeout?: number | undefined;
+    /** Hands the resolved addresses to net.connect */
+    lookup?: net.LookupFunction | undefined;
 }
 /**
  * A queued handler for the next server response

node_modules/nodemailer/dist/cjs/smtp-connection/index.js

@@ -45,12 +45,30 @@ const node_crypto_1 = __importDefault(require("node:crypto"));
 const data_stream_js_1 = __importDefault(require("./data-stream.js"));
 const node_stream_1 = require("node:stream");
 const shared = __importStar(require("../shared/index.js"));
+const errors_js_1 = require("../errors.js");
 // default timeout values in ms
 const CONNECTION_TIMEOUT = 2 * 60 * 1000; // how much to wait for the connection to be established
 const SOCKET_TIMEOUT = 10 * 60 * 1000; // how much to wait for socket inactivity before disconnecting the client
 const GREETING_TIMEOUT = 30 * 1000; // how much to wait after connection is established but SMTP greeting is not receieved
 const DNS_TIMEOUT = 30 * 1000; // how much to wait for resolveHostname
+const CLOSE_TIMEOUT = 5 * 1000; // how much to wait for the server to close its side after we closed ours
+const KEEPALIVE_DELAY = 30 * 1000; // idle time before TCP keepalive probes start, keeps NAT mappings of idle connections alive
 const TEARDOWN_NOOP = () => { }; // reusable no-op handler for absorbing errors during socket teardown
+// Random order, so that connections spread over the addresses of a host
+function shuffle(list) {
+    const result = list.slice();
+    for (let i = result.length - 1; i > 0; i--) {
+        const j = Math.floor(Math.random() * (i + 1));
+        [result[i], result[j]] = [result[j], result[i]];
+    }
+    return result;
+}
+// Every timeout is reported with the ETIMEDOUT code, timeoutType tells which one it was
+function timeoutError(message, timeoutType) {
+    const err = new Error(message);
+    err.timeoutType = timeoutType;
+    return err;
+}
 // how many bytes a single server response may occupy while it is still being received.
 // Generous compared to any real reply, it only stops a peer that never completes one
 const MAX_RESPONSE_SIZE = 1024 * 1024;
@@ -173,8 +191,8 @@ class SMTPConnection extends node_events_1.EventEmitter {
         this._maxAllowedSize = 0;
         this._responseActions = [];
         this._recipientQueue = [];
-        this._greetingTimeout = false;
+        this._phaseTimer = false;
-        this._connectionTimeout = false;
+        this._plaintextEhlo = false;
         this._destroyed = false;
         this._closing = false;
         this._currentDataStream = false;
@@ -185,14 +203,25 @@ class SMTPConnection extends node_events_1.EventEmitter {
         this._onSocketClose = () => this._onClose();
         this._onSocketEnd = () => this._onEnd();
         this._onSocketTimeout = () => this._onTimeout();
-        this._onConnectionSocketError = err => this._onConnectionError(err, 'ESOCKET');
+        this._onConnectionSocketError = err => this._onError(err, 'ESOCKET', false, 'CONN');
-        this._connectionAttemptId = 0;
     }
     /**
      * Creates a connection to a SMTP server and sets up connection
      * listener
      */
     connect(connectCallback) {
+        if (this._connectCalled && !this._destroyed) {
+            // A connection is opened once. A second call would open a second socket over the
+            // first one and run the session handlers of both against the same state
+            const err = this._formatError('Cannot connect - connect() was already called for this connection', 'ECONNECTION', false, 'API');
+            if (typeof connectCallback === 'function') {
+                setImmediate(() => connectCallback(err));
+                return;
+            }
+            this.logger.warn({ tnx: 'smtp' }, '%s', err.message);
+            return;
+        }
+        this._connectCalled = true;
         if (typeof connectCallback === 'function') {
             this._connectCallback = connectCallback;
             this.once('connect', () => {
@@ -207,11 +236,15 @@ class SMTPConnection extends node_events_1.EventEmitter {
                 return connectCallback(this._formatError(isDestroyedMessage, 'ECONNECTION', false, 'CONN'));
             }
         }
+        // connectionTimeout covers the whole of connecting: the DNS lookup and every address tried
+        const connectionTimeout = this.options.connectionTimeout || CONNECTION_TIMEOUT;
+        // a transport that first opened a proxy connection for this one sets when that started
+        this._connectionDeadline = (this._connectStartedAt || Date.now()) + connectionTimeout;
         let opts = {
             port: this.port,
             host: this.host,
             allowInternalNetworkInterfaces: this.allowInternalNetworkInterfaces,
-            timeout: this.options.dnsTimeout || DNS_TIMEOUT
+            timeout: Math.min(this.options.dnsTimeout || DNS_TIMEOUT, connectionTimeout)
         };
         if (this.options.localAddress) {
             opts.localAddress = this.options.localAddress;
@@ -240,7 +273,6 @@ class SMTPConnection extends node_events_1.EventEmitter {
             return this._resolveAndConnect(opts, _resolved => {
                 try {
                     this._socket.connect(this.port, this.host, () => {
-                        this._socket.setKeepAlive(true);
                         // a `secure` connection over a caller-provided socket must still
                         // perform the TLS handshake, otherwise AUTH and the message body
                         // would be sent in cleartext despite the caller requesting TLS
@@ -272,9 +304,40 @@ class SMTPConnection extends node_events_1.EventEmitter {
                 }
             }
             return this._resolveAndConnect(opts, resolved => {
-                // Store fallback addresses for retry on connection failure
+                let addresses = resolved._addresses || [];
-                this._fallbackAddresses = (resolved._addresses || []).filter(addr => addr !== opts.host);
+                if (opts.localAddress) {
-                this._connectOpts = Object.assign({}, opts);
+                    // a socket bound to an address of one family can not reach the other one
+                    const localFamily = node_net_1.default.isIPv6(opts.localAddress) ? 6 : 4;
+                    const sameFamily = addresses.filter(addr => node_net_1.default.isIP(addr) === localFamily);
+                    addresses = sameFamily.length ? sameFamily : addresses;
+                }
+                if (addresses.length > 1) {
+                    // net.connect tries the addresses in turn and moves on to the next one when an
+                    // attempt fails or takes too long. With both families it starts on IPv6 and
+                    // alternates (RFC 8305), so a host with a broken IPv6 path costs a fraction of
+                    // a second instead of a whole connection timeout
+                    const ipv6 = addresses.filter(addr => node_net_1.default.isIPv6(addr));
+                    const ipv4 = addresses.filter(addr => !node_net_1.default.isIPv6(addr));
+                    const ordered = shuffle(ipv6).concat(shuffle(ipv4));
+                    opts.host = this.host;
+                    opts.autoSelectFamily = true;
+                    if (!ipv6.length || !ipv4.length) {
+                        // a slow address of the only family gets its share of the time, not the
+                        // quarter second meant for an address family that does not work
+                        const remaining = this._connectionDeadline - Date.now();
+                        opts.autoSelectFamilyAttemptTimeout = Math.max(Math.floor(remaining / ordered.length), 10);
+                    }
+                    opts.lookup = ((hostname, lookupOptions, callback) => {
+                        if (lookupOptions && lookupOptions.all) {
+                            const all = ordered.map(address => ({ address, family: node_net_1.default.isIPv6(address) ? 6 : 4 }));
+                            return setImmediate(() => callback(null, all));
+                        }
+                        setImmediate(() => callback(null, ordered[0], node_net_1.default.isIPv6(ordered[0]) ? 6 : 4));
+                    });
+                }
+                else if (addresses.length) {
+                    opts.host = addresses[0];
+                }
                 this._connectToHost(opts, this.secureConnection);
             });
         }
@@ -321,20 +384,11 @@ class SMTPConnection extends node_events_1.EventEmitter {
         if (this._destroyed || this._closing) {
             return;
         }
-        this._connectionAttemptId++;
-        const currentAttemptId = this._connectionAttemptId;
         const connectFn = secure
             ? node_tls_1.default.connect
             : node_net_1.default.connect;
         try {
-            this._socket = connectFn(opts, () => {
+            this._socket = connectFn(opts, () => this._onConnect());
-                // Ignore callback if this is a stale connection attempt
-                if (this._connectionAttemptId !== currentAttemptId) {
-                    return;
-                }
-                this._socket.setKeepAlive(true);
-                this._onConnect();
-            });
             this._setupConnectionHandlers();
         }
         catch (E) {
@@ -347,51 +401,37 @@ class SMTPConnection extends node_events_1.EventEmitter {
      * @internal
      */
     _setupConnectionHandlers() {
-        this._connectionTimeout = setTimeout(() => {
+        this._startPhase(Math.max((this._connectionDeadline || Date.now()) - Date.now(), 0), timeoutError('Connection timeout', 'CONNECT_TIMEOUT'));
-            this._onConnectionError('Connection timeout', 'ETIMEDOUT');
-        }, this.options.connectionTimeout || CONNECTION_TIMEOUT);
         this._socket.on('error', this._onConnectionSocketError);
     }
     /**
-     * Handles connection errors with fallback to alternative addresses
+     * Starts the timer of a connection phase: connecting, waiting for the greeting or a TLS
+     * upgrade. The phases follow one another, so starting one ends the one before
      *
-     * @param err Error object or message
+     * @param timeout Time the phase may take
-     * @param code Error code
+     * @param err Error to fail with when it takes longer
      * @internal
      */
-    _onConnectionError(err, code) {
+    _startPhase(timeout, err) {
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
-        // Check if we have fallback addresses to try
+        this._phaseTimer = setTimeout(() => {
-        const canFallback = this._fallbackAddresses && this._fallbackAddresses.length && this.stage === 'init' && !this._destroyed;
+            this._phaseTimer = false;
-        if (!canFallback) {
+            this._onError(err, 'ETIMEDOUT', false, 'CONN');
-            // No more fallback addresses, report the error
+        }, timeout);
-            this._onError(err, code, false, 'CONN');
-            return;
     }
-        const nextHost = this._fallbackAddresses.shift();
+    /**
-        this.logger.info({
+     * Time the greeting or a STARTTLS upgrade may take: greetingTimeout, cut short by what is left
-            tnx: 'network',
+     * of connectionTimeout
-            failedHost: this._connectOpts.host,
+     *
-            nextHost,
+     * @internal
-            error: err.message || err
+     */
-        }, 'Connection to %s failed, trying %s', this._connectOpts.host, nextHost);
+    _remainingSetupTime() {
-        // Clean up current socket
+        return Math.min(this.options.greetingTimeout || GREETING_TIMEOUT, Math.max((this._connectionDeadline || Infinity) - Date.now(), 1));
-        if (this._socket) {
-            try {
-                this._socket.removeListener('error', this._onConnectionSocketError);
-                // Absorb any late teardown error (e.g. a TLS fallback socket emitting
-                // after destroy), mirroring the guard used in close()
-                this._socket.on('error', TEARDOWN_NOOP);
-                this._socket.destroy();
     }
-            catch (_E) {
+    /** @internal */
-                // ignore
+    _clearPhase() {
-            }
+        clearTimeout(this._phaseTimer);
-            this._socket = null;
+        this._phaseTimer = false;
-        }
-        // Update host and retry
-        this._connectOpts.host = nextHost;
-        this._connectToHost(this._connectOpts, this.secureConnection);
     }
     /**
      * Sends QUIT
@@ -404,8 +444,7 @@ class SMTPConnection extends node_events_1.EventEmitter {
      * Closes the connection to the server
      */
     close() {
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
-        clearTimeout(this._greetingTimeout);
         this._responseActions = [];
         // allow to run this function only once
         if (this._closing) {
@@ -428,13 +467,15 @@ class SMTPConnection extends node_events_1.EventEmitter {
             }
             this._currentDataStream = false;
         }
-        // Detach from the message stream as well. The listener is swapped for a no-op rather than
+        // Detach from the message stream as well and release whatever it reads from, the message
-        // removed, a stream destroyed with an error later on would otherwise throw it as unhandled
+        // can not be sent over this connection anymore. The listener is swapped for a no-op rather
+        // than removed, a stream destroyed with an error would otherwise throw it as unhandled
         if (this._pendingSend) {
             const { stream, onStreamError } = this._pendingSend;
             if (stream) {
                 stream.removeListener('error', onStreamError);
                 stream.on('error', TEARDOWN_NOOP);
+                stream.destroy();
             }
             this._pendingSend = false;
         }
@@ -453,6 +494,15 @@ class SMTPConnection extends node_events_1.EventEmitter {
                 // sending cleartext after TLS shutdown triggers ERR_SSL_BAD_RECORD_TYPE)
                 socket.on('error', TEARDOWN_NOOP);
                 socket[closeMethod]();
+                if (closeMethod === 'end') {
+                    // end() only closes our side, a server that never closes its own would keep
+                    // the socket, and the process with it, around for good
+                    const closeTimer = setTimeout(() => socket.destroy(), CLOSE_TIMEOUT);
+                    if (typeof closeTimer.unref === 'function') {
+                        closeTimer.unref();
+                    }
+                    socket.once('close', () => clearTimeout(closeTimer));
+                }
             }
             catch (_E) {
                 // just ignore
@@ -657,14 +707,9 @@ class SMTPConnection extends node_events_1.EventEmitter {
         const startTime = Date.now();
         this._setEnvelope(envelope, (err, info) => {
             if (err) {
-                // create passthrough stream to consume to prevent OOM
+                // the message is not going to be sent, release whatever the stream reads from
-                const stream = new node_stream_1.PassThrough();
+                if (typeof message.destroy === 'function') {
-                if (typeof message.pipe === 'function') {
+                    message.destroy();
-                    message.pipe(stream);
-                }
-                else {
-                    stream.write(message);
-                    stream.end();
                 }
                 return callback(err);
             }
@@ -718,7 +763,7 @@ class SMTPConnection extends node_events_1.EventEmitter {
      */
     _onConnect() {
         const socket = this._socket;
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
         this.logger.info({
             tnx: 'network',
             localAddress: socket.localAddress,
@@ -748,16 +793,42 @@ class SMTPConnection extends node_events_1.EventEmitter {
         socket.once('end', this._onSocketEnd);
         socket.setTimeout(this.options.socketTimeout || SOCKET_TIMEOUT);
         socket.on('timeout', this._onSocketTimeout);
-        this._greetingTimeout = setTimeout(() => {
+        // keepalive also covers sockets handed over by a proxy or by the caller
-            // if still waiting for greeting, give up
+        if (typeof socket.setKeepAlive === 'function') {
-            if (this._socket && !this._destroyed && this._responseActions[0] === this._actionGreeting) {
+            socket.setKeepAlive(true, KEEPALIVE_DELAY);
-                this._onError('Greeting never received', 'ETIMEDOUT', false, 'CONN');
         }
-        }, this.options.greetingTimeout || GREETING_TIMEOUT);
+        // Commands are written in the batches they belong to (see cork() for PIPELINING), Nagle
+        // would only hold a write back until the server acknowledged the previous one. Against a
+        // server that delays its ACKs that costs 40ms on every message
+        if (typeof socket.setNoDelay === 'function') {
+            socket.setNoDelay(true);
+        }
+        // bounded by greetingTimeout and by what is left of connectionTimeout, which covers setting
+        // the session up from the DNS lookup to the end of a STARTTLS upgrade
+        this._startPhase(this._remainingSetupTime(), timeoutError('Greeting never received', 'GREETING_TIMEOUT'));
         this._responseActions.push(this._actionGreeting);
         // we have a 'data' listener set up so resume socket if it was paused
         socket.resume();
     }
+    /**
+     * Ends the session after a 421 reply. The replies queued for commands sent along with the
+     * answered one are not going to come, so the message in flight is failed here
+     *
+     * @param str The 421 reply
+     * @internal
+     */
+    _onServerClosing(str) {
+        if (this._destroyed) {
+            return;
+        }
+        const pendingSend = this._pendingSend;
+        const envelope = this._envelope;
+        this._responseActions = [];
+        this.close();
+        if (pendingSend) {
+            pendingSend.callback((envelope && envelope.mailError) || this._formatError('Server closed the connection', 'ECONNECTION', str, 'CONN'));
+        }
+    }
     /**
      * 'data' listener for data coming from the server
      *
@@ -832,8 +903,7 @@ class SMTPConnection extends node_events_1.EventEmitter {
      * @internal
      */
     _onError(err, type, data, command) {
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
-        clearTimeout(this._greetingTimeout);
         if (this._destroyed) {
             // just ignore, already closed
             // this might happen when a socket is canceled because of reached timeout
@@ -841,12 +911,12 @@ class SMTPConnection extends node_events_1.EventEmitter {
             return;
         }
         err = this._formatError(err, type, data, command);
-        const transientCodes = ['ETIMEDOUT', 'ESOCKET', 'ECONNECTION'];
+        // the message carries the server response, it is an argument and not the format string
-        if (transientCodes.includes(err.code)) {
+        if ((0, errors_js_1.isTransientError)(err)) {
-            this.logger.warn(data, err.message);
+            this.logger.warn({ tnx: 'smtp', err }, '%s', err.message);
         }
         else {
-            this.logger.error(data, err.message);
+            this.logger.error({ tnx: 'smtp', err }, '%s', err.message);
         }
         // close() forgets the send in flight, it is completed with this same error afterwards so
         // a late message stream error has nothing left to report
@@ -866,7 +936,12 @@ class SMTPConnection extends node_events_1.EventEmitter {
         else {
             err = new Error(message);
         }
-        if (type && type !== 'Error') {
+        // a permission model denial keeps its own code, see ERR_ACCESS_DENIED
+        if (type && type !== 'Error' && err.code !== errors_js_1.ERR_ACCESS_DENIED) {
+            // the code of a system error, such as ECONNREFUSED, still tells what happened
+            if (err.code && err.code !== type && !err.originalCode) {
+                err.originalCode = err.code;
+            }
             err.code = type;
         }
         if (response) {
@@ -918,6 +993,19 @@ class SMTPConnection extends node_events_1.EventEmitter {
             this.close();
             return;
         }
+        if (!failureResponse &&
+            this.stage === 'connected' &&
+            !this._responseActions.length &&
+            !this._pendingSend &&
+            !this._destroyed &&
+            !this._closing) {
+            // nothing was waiting for the server, so this is the server ending an idle session
+            // (usually after its idle timeout), not a failure
+            this.logger.info({
+                tnx: 'network'
+            }, 'Server closed the idle connection');
+            return this._destroy();
+        }
         if (failureResponse || (this._responseActions[0] !== this.close && !this._destroyed)) {
             return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', failureResponse, 'CONN');
         }
@@ -943,7 +1031,7 @@ class SMTPConnection extends node_events_1.EventEmitter {
      * @internal
      */
     _onTimeout() {
-        return this._onError(new Error('Timeout'), 'ETIMEDOUT', false, 'CONN');
+        return this._onError(timeoutError('Timeout', 'SOCKET_TIMEOUT'), 'ETIMEDOUT', false, 'CONN');
     }
     /**
      * Destroys the client, emits 'end'
@@ -958,10 +1046,7 @@ class SMTPConnection extends node_events_1.EventEmitter {
         this.destroyed = true;
         // a connection the server dropped before the greeting would otherwise keep
         // the greeting timer, and with it the process, alive until it fires
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
-        clearTimeout(this._greetingTimeout);
-        this._connectionTimeout = false;
-        this._greetingTimeout = false;
         this.emit('end');
     }
     /**
@@ -978,6 +1063,15 @@ class SMTPConnection extends node_events_1.EventEmitter {
         // inject plaintext bytes after the "220" reply (e.g. a CRLF-free fragment that
         // would otherwise be prepended to the first post-TLS response and parsed as
         // part of the secured EHLO capabilities). STARTTLS response injection.
+        const discarded = this._remainder.length + this._responseQueue.reduce((total, response) => total + response.length, 0);
+        if (discarded) {
+            // a server does not send anything here on its own, this is worth knowing about
+            this.logger.warn({
+                tnx: 'smtp',
+                discarded
+            }, 'Discarded %s bytes received in plaintext after the STARTTLS response', discarded);
+        }
+        this._plaintextEhlo = false;
         this._remainder = '';
         this._responseQueue = [];
         this._responsePartial = false;
@@ -987,6 +1081,7 @@ class SMTPConnection extends node_events_1.EventEmitter {
         const socketPlain = this._socket;
         socketPlain.removeListener('data', this._onSocketData); // incoming data is going to be gibberish from this point onwards
         socketPlain.removeListener('timeout', this._onSocketTimeout); // timeout will be re-set for the new socket object
+        socketPlain.setTimeout(0);
         const opts = Object.assign({
             socket: socketPlain,
             host: this.host
@@ -1007,9 +1102,14 @@ class SMTPConnection extends node_events_1.EventEmitter {
             socketPlain.removeListener('error', this._onConnectionSocketError);
         };
         this.upgrading = true;
+        // the socket timeout only notices a server that sends nothing at all, a handshake that
+        // trickles along would otherwise hold the connection for as long as the server likes
+        // STARTTLS is the last step of setting the session up
+        this._startPhase(this._remainingSetupTime(), timeoutError('TLS handshake timed out', 'UPGRADE_TIMEOUT'));
         // tls.connect is not an asynchronous function however it may still throw errors and requires to be wrapped with try/catch
         try {
             this._socket = node_tls_1.default.connect(opts, () => {
+                this._clearPhase();
                 this.secure = true;
                 this.upgrading = false;
                 this._socket.on('data', this._onSocketData);
@@ -1018,6 +1118,7 @@ class SMTPConnection extends node_events_1.EventEmitter {
             });
         }
         catch (err) {
+            this._clearPhase();
             removePlainSocketListeners();
             return callback(err);
         }
@@ -1058,10 +1159,24 @@ class SMTPConnection extends node_events_1.EventEmitter {
             }, str.replace(/\r?\n$/, ''));
         }
         const action = this._responseActions.shift();
+        // RFC 5321 4.2: 421 means the server is about to close the connection, whatever it answers
+        const closing = /^421[ -]/.test(str);
         if (typeof action === 'function') {
+            // the command gets its own error first, the code tells which step failed
             action.call(this, str);
+            if (closing) {
+                return this._onServerClosing(str);
+            }
             setImmediate(() => this._processResponse());
         }
+        else if (closing && !this._pendingSend && this.stage === 'connected') {
+            // RFC 5321 4.2: a server may send 421 at any time when it is about to close the
+            // connection. Nothing was waiting for a reply, so this ends an idle session
+            this.logger.info({
+                tnx: 'smtp'
+            }, 'Server closed the idle connection: %s', str);
+            this.close();
+        }
         else {
             return this._onError(new Error('Unexpected Response'), 'EPROTOCOL', str, 'CONN');
         }
@@ -1156,6 +1271,9 @@ class SMTPConnection extends node_events_1.EventEmitter {
                 return callback(this._formatError('Server does not support REQUIRETLS extension (RFC 8689)', 'EREQUIRETLS', false, 'MAIL FROM'));
             }
         }
+        // RFC 2920: with PIPELINING the whole envelope and DATA go out without waiting for the
+        // replies in between, which saves two round trips for every message
+        this._envelope.pipelined = this._supportedExtensions.includes('PIPELINING');
         this._responseActions.push(str => {
             this._actionMAIL(str, callback);
         });
@@ -1193,7 +1311,38 @@ class SMTPConnection extends node_events_1.EventEmitter {
         if (this._envelope.requireTLSExtensionEnabled) {
             args.push('REQUIRETLS');
         }
-        this._sendCommand('MAIL FROM:<' + this._envelope.from + '>' + (args.length ? ' ' + args.join(' ') : ''));
+        const mailFrom = 'MAIL FROM:<' + this._envelope.from + '>' + (args.length ? ' ' + args.join(' ') : '');
+        this._recipientQueue = [];
+        if (!this._envelope.pipelined) {
+            this._sendCommand(mailFrom);
+            return;
+        }
+        // corked, so the batch leaves in one segment instead of the first command alone
+        const socket = this._socket;
+        socket.cork();
+        this._sendCommand(mailFrom);
+        while (this._envelope.rcptQueue.length) {
+            this._sendRcpt(this._envelope.rcptQueue.shift(), callback);
+        }
+        this._responseActions.push(str => {
+            this._actionDATA(str, callback);
+        });
+        this._sendCommand('DATA');
+        socket.uncork();
+    }
+    /**
+     * Sends RCPT TO for a recipient and queues the handler for the reply
+     *
+     * @param recipient Recipient address
+     * @param callback Callback to run once the envelope is processed
+     * @internal
+     */
+    _sendRcpt(recipient, callback) {
+        this._recipientQueue.push(recipient);
+        this._responseActions.push(str => {
+            this._actionRCPT(str, callback);
+        });
+        this._sendCommand('RCPT TO:<' + recipient + '>' + this._getDsnRcptToArgs());
     }
     /** @internal */
     _setDsnEnvelope(params) {
@@ -1309,7 +1458,7 @@ class SMTPConnection extends node_events_1.EventEmitter {
      * @internal
      */
     _actionGreeting(str) {
-        clearTimeout(this._greetingTimeout);
+        this._clearPhase();
         if (str.substr(0, 3) !== '220') {
             this._onError(new Error('Invalid greeting. response=' + str), 'EPROTOCOL', str, 'CONN');
             return;
@@ -1347,7 +1496,6 @@ class SMTPConnection extends node_events_1.EventEmitter {
      * @internal
      */
     _actionEHLO(str) {
-        let match;
         if (str.substr(0, 3) === '421') {
             this._onError(new Error('Server terminates connection. response=' + str), 'ECONNECTION', str, 'EHLO');
             return;
@@ -1362,17 +1510,30 @@ class SMTPConnection extends node_events_1.EventEmitter {
             this._sendCommand('HELO ' + this.name);
             return;
         }
+        // Detect if the server supports STARTTLS
+        if (!this.secure && !this.options.ignoreTLS && (/[ -]STARTTLS\b/im.test(str) || this.options.requireTLS)) {
+            // kept for opportunisticTLS, a session that stays in plaintext still has these extensions
+            this._plaintextEhlo = str;
+            this._sendCommand('STARTTLS');
+            this._responseActions.push(this._actionSTARTTLS);
+            return;
+        }
+        this._parseEhloExtensions(str);
+        this.emit('connect');
+    }
+    /**
+     * Reads the extensions and the authentication mechanisms out of an EHLO response
+     *
+     * @param str EHLO response from the server
+     * @internal
+     */
+    _parseEhloExtensions(str) {
+        let match;
         this._ehloLines = str
             .split(/\r?\n/)
             .map(line => line.replace(/^\d+[ -]/, '').trim())
             .filter(line => line)
             .slice(1);
-        // Detect if the server supports STARTTLS
-        if (!this.secure && !this.options.ignoreTLS && (/[ -]STARTTLS\b/im.test(str) || this.options.requireTLS)) {
-            this._sendCommand('STARTTLS');
-            this._responseActions.push(this._actionSTARTTLS);
-            return;
-        }
         // Detect if the server supports SMTPUTF8
         if (/[ -]SMTPUTF8\b/im.test(str)) {
             this._supportedExtensions.push('SMTPUTF8');
@@ -1422,7 +1583,6 @@ class SMTPConnection extends node_events_1.EventEmitter {
             this._supportedExtensions.push('SIZE');
             this._maxAllowedSize = Number(match[1]) || 0;
         }
-        this.emit('connect');
     }
     /**
      * Handles server response for HELO command. If it yielded in
@@ -1454,6 +1614,14 @@ class SMTPConnection extends node_events_1.EventEmitter {
                 this.logger.info({
                     tnx: 'smtp'
                 }, 'Failed STARTTLS upgrade, continuing unencrypted');
+                // the plaintext session goes on with what the server announced for it, except for
+                // AUTH: credentials are not sent over a connection that failed to encrypt
+                if (this._plaintextEhlo) {
+                    this._parseEhloExtensions(this._plaintextEhlo);
+                    this._plaintextEhlo = false;
+                    this.allowsAuth = false;
+                    this._supportedAuth = [];
+                }
                 this.emit('connect');
                 return;
             }
@@ -1634,21 +1802,9 @@ class SMTPConnection extends node_events_1.EventEmitter {
             const message = this._usingSmtpUtf8 && /^550 /.test(str) && /[\x80-\uFFFF]/.test(envelope.from)
                 ? 'Internationalized mailbox name not allowed'
                 : 'Mail command failed';
-            return callback(this._formatError(message, 'EENVELOPE', str, 'MAIL FROM'));
+            envelope.mailError = this._formatError(message, 'EENVELOPE', str, 'MAIL FROM');
         }
-        if (!envelope.rcptQueue.length) {
+        this._advanceEnvelope(str, callback);
-            return callback(this._formatError("Can't send mail - no recipients defined", 'EENVELOPE', false, 'API'));
-        }
-        this._recipientQueue = [];
-        const usePipelining = this._supportedExtensions.includes('PIPELINING');
-        do {
-            const curRecipient = envelope.rcptQueue.shift();
-            this._recipientQueue.push(curRecipient);
-            this._responseActions.push(str => {
-                this._actionRCPT(str, callback);
-            });
-            this._sendCommand('RCPT TO:<' + curRecipient + '>' + this._getDsnRcptToArgs());
-        } while (usePipelining && envelope.rcptQueue.length);
     }
     /**
      * Handle response for a RCPT TO: command
@@ -1675,32 +1831,67 @@ class SMTPConnection extends node_events_1.EventEmitter {
         else {
             envelope.accepted.push(curRecipient);
         }
-        if (!envelope.rcptQueue.length && !this._recipientQueue.length) {
+        this._advanceEnvelope(str, callback);
-            if (envelope.rejected.length < envelope.to.length) {
+    }
+    /**
+     * Moves the envelope on after a reply to MAIL FROM or RCPT TO. A pipelined envelope sent every
+     * command at once and is decided by the reply to DATA. Otherwise the commands go one at a
+     * time: the next recipient, or once every reply is in, DATA or the error that ends the message
+     *
+     * @param str The reply that was handled
+     * @param callback Callback to run once the envelope is processed
+     * @internal
+     */
+    _advanceEnvelope(str, callback) {
+        const envelope = this._envelope;
+        if (envelope.pipelined) {
+            return;
+        }
+        if (envelope.mailError) {
+            return callback(envelope.mailError);
+        }
+        if (envelope.rcptQueue.length) {
+            return this._sendRcpt(envelope.rcptQueue.shift(), callback);
+        }
+        if (this._recipientQueue.length) {
+            // replies still to come
+            return;
+        }
+        const err = this._envelopeError(str);
+        if (err) {
+            return callback(err);
+        }
         this._responseActions.push(str => {
             this._actionDATA(str, callback);
         });
         this._sendCommand('DATA');
     }
-            else {
+    /**
+     * Decides how the envelope went once every reply to MAIL FROM and RCPT TO is in. Called after
+     * the last RCPT TO reply, or with PIPELINING on the reply to the DATA command sent along
+     *
+     * @param str The reply being handled
+     * @returns The error to fail the message with, or null when DATA can go ahead
+     * @internal
+     */
+    _envelopeError(str) {
+        const envelope = this._envelope;
+        if (envelope.mailError) {
+            return envelope.mailError;
+        }
+        if (envelope.accepted.length) {
+            return null;
+        }
         // report a temporary rejection when there is one, taking the last reply would mark the
         // whole message as permanently failed although some recipients were only deferred
         const deferred = envelope.rejectedErrors.find(rejectedErr => rejectedErr.responseCode && rejectedErr.responseCode < 500);
-                const reply = deferred?.response ?? str;
+        const lastRejected = envelope.rejectedErrors[envelope.rejectedErrors.length - 1];
-                err = this._formatError("Can't send mail - all recipients were rejected", 'EENVELOPE', reply, 'RCPT TO');
+        const reply = deferred?.response ?? (envelope.pipelined && lastRejected ? lastRejected.response : str);
+        // every recipient was rejected
+        const err = this._formatError("Can't send mail - all recipients were rejected", 'EENVELOPE', reply, 'RCPT TO');
         err.rejected = envelope.rejected;
         err.rejectedErrors = envelope.rejectedErrors;
-                return callback(err);
+        return err;
-            }
-        }
-        else if (envelope.rcptQueue.length) {
-            const nextRecipient = envelope.rcptQueue.shift();
-            this._recipientQueue.push(nextRecipient);
-            this._responseActions.push(str => {
-                this._actionRCPT(str, callback);
-            });
-            this._sendCommand('RCPT TO:<' + nextRecipient + '>' + this._getDsnRcptToArgs());
-        }
     }
     /**
      * Handle response for a DATA command
@@ -1711,6 +1902,27 @@ class SMTPConnection extends node_events_1.EventEmitter {
      */
     _actionDATA(str, callback) {
         const envelope = this._envelope;
+        if (envelope.pipelined) {
+            const err = this._envelopeError(str);
+            if (err) {
+                if (/^3/.test(str)) {
+                    if (envelope.mailError) {
+                        // A server that refused the sender has no transaction to end, one that
+                        // took DATA anyway can not be trusted with an empty message either.
+                        // Drop the connection instead of answering it
+                        this.close();
+                        return callback(err);
+                    }
+                    // A server must refuse DATA without an accepted recipient, this one took it
+                    // anyway. End the empty message, it has nobody to go to, so the session
+                    // stays usable
+                    this._responseActions.push(() => callback(err));
+                    this._sendCommand('.');
+                    return;
+                }
+                return callback(err);
+            }
+        }
         // response should be 354 but according to this issue https://github.com/eleith/emailjs/issues/24
         // some servers might use 250 instead, so lets check for 2 or 3 as the first digit
         if (!/^[23]/.test(str)) {

node_modules/nodemailer/dist/cjs/smtp-pool/index.d.ts

@@ -19,6 +19,8 @@ export interface SMTPPoolOptions extends SMTPTransportOptions {
     rateDelta?: number | undefined;
     /** How many times a message is requeued when its connection closes while sending, defaults to 5, a negative value means unlimited */
     maxRequeues?: number | undefined;
+    /** Time in milliseconds a connection may stay idle before it is closed, defaults to 4 minutes, 0 keeps it open until the server closes it */
+    idleTimeout?: number | undefined;
 }
 /**
  * The pool options once the constructor has applied the defaults
@@ -27,6 +29,7 @@ export type SMTPPoolResolvedOptions = SMTPPoolOptions & {
     maxConnections: number;
     maxMessages: number;
     maxRequeues: number;
+    idleTimeout: number;
 };
 /**
  * Result of a message sent through the pool, same as for the SMTP transport

node_modules/nodemailer/dist/cjs/smtp-pool/index.js

@@ -80,6 +80,9 @@ class SMTPPool extends node_events_1.EventEmitter {
         this.options.maxMessages = this.options.maxMessages || 100;
         // a default bound, a server that closes every connection before the greeting would otherwise be retried forever
         this.options.maxRequeues = typeof this.options.maxRequeues === 'number' ? this.options.maxRequeues : 5;
+        // below the 5 minutes RFC 5321 asks servers to wait at least, the connection is closed by us
+        // and not by the server in the middle of handing it a message
+        this.options.idleTimeout = typeof this.options.idleTimeout === 'number' ? this.options.idleTimeout : 4 * 60 * 1000;
         this.logger = shared.getLogger(this.options, {
             component: this.options.component || 'smtp-pool'
         });
@@ -486,7 +489,9 @@ class SMTPPool extends node_events_1.EventEmitter {
         // the error paths hand over the error alone
         const done = callback;
         const auth = new pool_resource_js_1.default(this).auth;
-        this.getSocket(this.options, (err, socketOptions) => {
+        // the proxy handshake, if any, counts against connectionTimeout as well
+        const connectStartedAt = Date.now();
+        this.getSocket(Object.assign({}, this.options, { connectStartedAt }), (err, socketOptions) => {
             if (err) {
                 return done(err);
             }
@@ -503,6 +508,7 @@ class SMTPPool extends node_events_1.EventEmitter {
                 options = Object.assign(shared.assign(false, options), socketOptions);
             }
             const connection = new index_js_1.default(options);
+            connection._connectStartedAt = connectStartedAt;
             let returned = false;
             connection.once('error', err => {
                 if (returned) {

node_modules/nodemailer/dist/cjs/smtp-pool/pool-resource.js

@@ -90,6 +90,8 @@ class PoolResource extends node_events_1.EventEmitter {
         this.messages = 0;
         this.available = true;
         this._failed = false;
+        this._sending = false;
+        this._idleTimer = false;
     }
     /**
      * Emits 'error' for the first failure only. A dead resource can report the same failure more
@@ -109,7 +111,9 @@ class PoolResource extends node_events_1.EventEmitter {
      * @param callback Callback function to run once the connection is established or failed
      */
     connect(callback) {
-        this.pool.getSocket(this.options, (err, socketOptions) => {
+        // the proxy handshake, if any, counts against connectionTimeout as well
+        const connectStartedAt = Date.now();
+        this.pool.getSocket(Object.assign({}, this.options, { connectStartedAt }), (err, socketOptions) => {
             if (err) {
                 // nothing was connected, so no 'close' event is coming that would free the
                 // slot this resource holds in the pool, report the failure the way a failed
@@ -131,7 +135,21 @@ class PoolResource extends node_events_1.EventEmitter {
                 options = Object.assign((0, index_js_2.assign)(false, options), socketOptions);
             }
             this.connection = new index_js_1.default(options);
-            this.connection.on('error', err => {
+            this.connection._connectStartedAt = connectStartedAt;
+            this.connection.on('error', (err) => {
+                if (this._sending) {
+                    // the send callback gets the same error and decides what it means for the message
+                    return;
+                }
+                if (this._connected && errors.isTransientError(err)) {
+                    // the server ended a connection that had nothing in flight, usually after it
+                    // was idle for a while. The 'end' that follows closes this resource
+                    this.logger.info({
+                        tnx: 'pool',
+                        cid: this.id
+                    }, 'Connection #%s was closed by the server: %s', this.id, err.message);
+                    return;
+                }
                 this._fail(err);
                 if (returned) {
                     return;
@@ -209,9 +227,39 @@ class PoolResource extends node_events_1.EventEmitter {
         if (mail.data.requireTLSExtensionEnabled) {
             envelope.requireTLSExtensionEnabled = mail.data.requireTLSExtensionEnabled;
         }
-        this.connection.send(envelope, mail.message.createReadStream(), (err, info) => {
+        this._sending = true;
+        // a connection that sent messages before may have been dropped by the server in between
+        const reused = this.messages > 0;
+        const messageStream = mail.message.createReadStream();
+        this.connection.send(envelope, messageStream, (err, info) => {
+            this._sending = false;
             this.messages++;
             if (err) {
+                if (reused && messageStream.readableDidRead === false && errors.isTransientError(err)) {
+                    // Not a byte of the message was sent, so it can go out over another
+                    // connection. The pool requeues the message when this resource closes
+                    this.logger.info({
+                        tnx: 'pool',
+                        cid: this.id,
+                        messageId
+                    }, 'Connection #%s was closed by the server before message %s was sent: %s', this.id, messageId, err.message);
+                    this.connection.close();
+                    return;
+                }
+                if ((err.code === errors.EENVELOPE || err.code === errors.EMESSAGE) &&
+                    err.responseCode !== 421 &&
+                    !this.connection._destroyed) {
+                    // The server refused this message, the connection itself is fine. Reset the
+                    // session and keep using it instead of opening a new one
+                    this.connection.reset(resetErr => {
+                        if (resetErr) {
+                            this.connection.close();
+                            return;
+                        }
+                        this._release();
+                    });
+                    return callback(err);
+                }
                 this.connection.close();
                 this._fail(err);
                 return callback(err);
@@ -221,28 +269,69 @@ class PoolResource extends node_events_1.EventEmitter {
                 to: envelope.to
             };
             info.messageId = messageId;
-            setImmediate(() => {
+            setImmediate(() => this._release());
+            callback(null, info);
+        });
+    }
+    /**
+     * Makes the connection available for the next message, or closes it once it has sent
+     * maxMessages messages
+     *
+     * @internal
+     */
+    _release() {
         if (this.messages >= this.options.maxMessages) {
             const err = new Error('Resource exhausted');
             err.code = errors.EMAXLIMIT;
             this.connection.close();
             this._fail(err);
+            return;
         }
-                else {
         this.pool._checkRateLimit(() => {
             this.available = true;
+            this._startIdleTimer();
             this.emit('available');
         });
     }
-            });
+    /** @internal */
-            callback(null, info);
+    _startIdleTimer() {
-        });
+        if (!this.options.idleTimeout || this.options.idleTimeout < 0) {
+            return;
+        }
+        // one timer per connection, restarted every time the connection becomes available. A
+        // connection that is busy when it fires is simply not closed
+        if (this._idleTimer && typeof this._idleTimer.refresh === 'function') {
+            this._idleTimer.refresh();
+            return;
+        }
+        clearTimeout(this._idleTimer);
+        this._idleTimer = setTimeout(() => {
+            if (!this.available) {
+                return;
+            }
+            this.logger.debug({
+                tnx: 'pool',
+                cid: this.id
+            }, 'Closing connection #%s after it was idle for %sms', this.id, this.options.idleTimeout);
+            // not handed another message while it says goodbye
+            this.available = false;
+            this.connection.quit();
+        }, this.options.idleTimeout);
+        if (typeof this._idleTimer.unref === 'function') {
+            this._idleTimer.unref();
+        }
+    }
+    /** @internal */
+    _stopIdleTimer() {
+        clearTimeout(this._idleTimer);
+        this._idleTimer = false;
     }
     /**
      * Closes the connection
      */
     close() {
         this._connected = false;
+        this._stopIdleTimer();
         if (this.auth && this.auth.oauth2) {
             this.auth.oauth2.removeAllListeners();
         }

node_modules/nodemailer/dist/cjs/smtp-transport/index.js

@@ -142,7 +142,9 @@ class SMTPTransport extends node_events_1.EventEmitter {
      * @param callback Callback function
      */
     send(mail, callback) {
-        this.getSocket(this.options, (err, socketOptions) => {
+        // the proxy handshake, if any, counts against connectionTimeout as well
+        const connectStartedAt = Date.now();
+        this.getSocket(Object.assign({}, this.options, { connectStartedAt }), (err, socketOptions) => {
             if (err) {
                 return callback(err);
             }
@@ -161,6 +163,7 @@ class SMTPTransport extends node_events_1.EventEmitter {
                 options = Object.assign(shared.assign(false, options), socketOptions);
             }
             const connection = new index_js_1.default(options);
+            connection._connectStartedAt = connectStartedAt;
             let perCallAuth;
             const cleanupPerCallAuth = () => {
                 if (perCallAuth && perCallAuth !== this.auth && perCallAuth.oauth2) {
@@ -266,7 +269,9 @@ class SMTPTransport extends node_events_1.EventEmitter {
         }
         // the error paths hand over the error alone
         const done = callback;
-        this.getSocket(this.options, (err, socketOptions) => {
+        // the proxy handshake, if any, counts against connectionTimeout as well
+        const connectStartedAt = Date.now();
+        this.getSocket(Object.assign({}, this.options, { connectStartedAt }), (err, socketOptions) => {
             if (err) {
                 return done(err);
             }
@@ -283,6 +288,7 @@ class SMTPTransport extends node_events_1.EventEmitter {
                 options = Object.assign(shared.assign(false, options), socketOptions);
             }
             const connection = new index_js_1.default(options);
+            connection._connectStartedAt = connectStartedAt;
             let returned = false;
             let perCallAuth;
             const cleanupPerCallAuth = () => {

node_modules/nodemailer/dist/esm/addressparser/index.js

@@ -668,7 +668,11 @@ class Tokenizer {
             this.escaped = false;
             return;
         }
-        else if (['"', "'"].includes(this.operatorExpecting) && chr === '\\') {
+        else if (['"', "'", ')'].includes(this.operatorExpecting) && chr === '\\') {
+            // A backslash escapes the next character inside a quoted string and inside a
+            // comment alike (RFC 5322 3.2.2, ccontent includes quoted-pair). Honouring it
+            // only in quoted strings let an escaped parenthesis close the comment, which
+            // released the rest of it, an address included, into the header
             this.escaped = true;
             return;
         }

node_modules/nodemailer/dist/esm/base64/index.d.ts

@@ -24,6 +24,9 @@ export interface EncoderOptions {
 /**
  * Creates a transform stream for encoding data to base64 encoding
  *
+ * The output is the same as `wrap(encode(input), lineLength)` no matter how the input is split
+ * into chunks: every line but the last one ends with a line break, the last one does not
+ *
  * @constructor
  * @param options Stream options
  * @param [options.lineLength=76] Maximum length for lines, set to false to disable wrapping

node_modules/nodemailer/dist/esm/base64/index.js

@@ -11,6 +11,47 @@ export function encode(buffer) {
     }
     return buffer.toString('base64');
 }
+/**
+ * Turns a line length option into a whole number of characters, the default for anything unusable
+ */
+function normalizeLineLength(lineLength) {
+    const length = Math.floor(Number(lineLength));
+    return Number.isFinite(length) && length >= 1 ? length : 76;
+}
+/**
+ * Splits the bytes of `src` into lines of `lineLength` bytes, each followed by a line break. With
+ * `final` set the last line, which may be shorter, gets no line break; otherwise only complete
+ * lines are taken and the rest is left for the caller
+ *
+ * @param src Bytes to wrap
+ * @param lineLength Line length
+ * @param final Whether `src` ends the output
+ * @returns The wrapped bytes and the number of trailing bytes not taken
+ */
+function wrapBuffer(src, lineLength, final) {
+    const lines = Math.ceil(src.length / lineLength);
+    // the last line waits for more data unless this is the end: whether it gets a line break
+    // depends on whether anything follows it
+    const complete = Math.max(lines - 1, 0);
+    let rest = src.length - complete * lineLength;
+    const output = Buffer.allocUnsafe(complete * (lineLength + 2) + (final ? rest : 0));
+    let to = 0;
+    for (let from = 0; from < complete * lineLength; from += lineLength) {
+        src.copy(output, to, from, from + lineLength);
+        to += lineLength;
+        output[to++] = 0x0d;
+        output[to++] = 0x0a;
+    }
+    if (final) {
+        to += src.copy(output, to, complete * lineLength);
+        rest = 0;
+    }
+    if (to !== output.length) {
+        // never hand out bytes of the unfilled allocation
+        throw new Error('Unexpected wrapped length');
+    }
+    return { output, rest };
+}
 /**
  * Adds soft line breaks to a base64 string
  *
@@ -39,6 +80,9 @@ export function wrap(str, lineLength) {
 /**
  * Creates a transform stream for encoding data to base64 encoding
  *
+ * The output is the same as `wrap(encode(input), lineLength)` no matter how the input is split
+ * into chunks: every line but the last one ends with a line break, the last one does not
+ *
  * @constructor
  * @param options Stream options
  * @param [options.lineLength=76] Maximum length for lines, set to false to disable wrapping
@@ -48,66 +92,61 @@ export class Encoder extends Transform {
         super();
         this.options = options || {};
         if (this.options.lineLength !== false) {
-            this.options.lineLength = this.options.lineLength || 76;
+            this.options.lineLength = normalizeLineLength(this.options.lineLength);
         }
         this._curLine = '';
         this._remainingBytes = false;
         this.inputBytes = 0;
         this.outputBytes = 0;
     }
+    /**
+     * Emits the encoded characters `b64` that follow the current line, keeping what can not be
+     * emitted yet as the new current line
+     *
+     * @internal
+     */
+    _emit(b64, final) {
+        const src = Buffer.from(this._curLine + b64, 'latin1');
+        if (!src.length) {
+            return;
+        }
+        let output = src;
+        if (this.options.lineLength) {
+            const wrapped = wrapBuffer(src, this.options.lineLength, final);
+            output = wrapped.output;
+            this._curLine = wrapped.rest ? src.toString('latin1', src.length - wrapped.rest) : '';
+        }
+        else {
+            this._curLine = '';
+        }
+        if (output.length) {
+            this.outputBytes += output.length;
+            this.push(output);
+        }
+    }
     /** @internal */
     _transform(chunk, encoding, done) {
         let buf = encoding !== 'buffer' ? Buffer.from(chunk, encoding) : chunk;
         if (!buf || !buf.length) {
-            setImmediate(done);
+            return done();
-            return;
         }
         this.inputBytes += buf.length;
-        if (this._remainingBytes && this._remainingBytes.length) {
+        if (this._remainingBytes) {
             buf = Buffer.concat([this._remainingBytes, buf], this._remainingBytes.length + buf.length);
             this._remainingBytes = false;
         }
-        if (buf.length % 3) {
+        const extra = buf.length % 3;
-            this._remainingBytes = buf.slice(buf.length - (buf.length % 3));
+        if (extra) {
-            buf = buf.slice(0, buf.length - (buf.length % 3));
+            this._remainingBytes = buf.subarray(buf.length - extra);
+            buf = buf.subarray(0, buf.length - extra);
         }
-        else {
+        this._emit(encode(buf), false);
-            this._remainingBytes = false;
+        done();
-        }
-        let b64 = this._curLine + encode(buf);
-        if (this.options.lineLength) {
-            b64 = wrap(b64, this.options.lineLength);
-            // remove last line as it is still most probably incomplete
-            const lastLF = b64.lastIndexOf('\n');
-            if (lastLF < 0) {
-                this._curLine = b64;
-                b64 = '';
-            }
-            else if (lastLF === b64.length - 1) {
-                this._curLine = '';
-            }
-            else {
-                this._curLine = b64.substring(lastLF + 1);
-                b64 = b64.substring(0, lastLF + 1);
-            }
-        }
-        if (b64) {
-            this.outputBytes += b64.length;
-            this.push(Buffer.from(b64, 'ascii'));
-        }
-        setImmediate(done);
     }
     /** @internal */
     _flush(done) {
-        if (this._remainingBytes && this._remainingBytes.length) {
+        this._emit(this._remainingBytes ? encode(this._remainingBytes) : '', true);
-            this._curLine += encode(this._remainingBytes);
+        this._remainingBytes = false;
-        }
-        if (this._curLine) {
-            this._curLine = wrap(this._curLine, this.options.lineLength);
-            this.outputBytes += this._curLine.length;
-            this.push(Buffer.from(this._curLine, 'ascii'));
-            this._curLine = '';
-        }
         done();
     }
 }

node_modules/nodemailer/dist/esm/dkim/index.js

@@ -32,34 +32,47 @@ class DKIMSigner {
         this.output = output;
         this.output.usingCache = false;
         this.hasErrored = false;
-        this.input.on('error', err => {
+        this.input.on('error', err => this.fail(err));
+        // A consumer that goes away before the signed message was read in full destroys the
+        // output. Stop reading the input and drop the cache file instead of leaving them open
+        this.output.once('close', () => {
+            if (this.output.writableFinished) {
+                return;
+            }
+            this.hasErrored = true;
+            this.input.unpipe();
+            this.input.destroy();
+            this.cleanup();
+        });
+    }
+    /**
+     * Ends the output with an error and releases the cache file
+     */
+    fail(err) {
         this.hasErrored = true;
         this.cleanup();
-            output.emit('error', err);
+        this.output.destroy(err);
-        });
     }
     cleanup() {
         if (!this.cache || !this.cachePath) {
             return;
         }
+        const cache = this.cache;
+        this.cache = false;
+        cache.destroy();
         fs.unlink(this.cachePath, () => false);
     }
     createReadCache() {
         // pipe remainings to cache file
         this.cache = fs.createReadStream(this.cachePath);
-        this.cache.once('error', err => {
+        this.cache.once('error', err => this.fail(err));
-            this.cleanup();
-            this.output.emit('error', err);
-        });
         this.cache.once('close', () => {
             this.cleanup();
         });
         this.cache.pipe(this.output);
     }
     sendNextChunk() {
-        if (this.hasErrored) {
+        while (!this.hasErrored) {
-            return;
-        }
             if (this.readPos >= this.chunks.length) {
                 if (!this.cache) {
                     this.output.end();
@@ -74,9 +87,12 @@ class DKIMSigner {
                 });
                 return;
             }
-        setImmediate(() => this.sendNextChunk());
+        }
     }
     sendSignedOutput() {
+        if (this.hasErrored) {
+            return;
+        }
         let keyPos = 0;
         const signNextKey = () => {
             if (keyPos >= this.keys.length) {
@@ -96,9 +112,7 @@ class DKIMSigner {
                 });
             }
             catch (err) {
-                this.hasErrored = true;
+                this.fail(err);
-                this.cleanup();
-                this.output.emit('error', err);
                 return;
             }
             if (dkimField) {
@@ -117,7 +131,6 @@ class DKIMSigner {
         // pipe remainings to cache file
         this.cache = fs.createWriteStream(this.cachePath);
         this.cache.once('error', err => {
-            this.cleanup();
             // drain input
             this.relaxedBody.unpipe(this.cache);
             this.relaxedBody.on('readable', () => {
@@ -125,11 +138,12 @@ class DKIMSigner {
                     // do nothing
                 }
             });
-            this.hasErrored = true;
+            this.fail(err);
-            // emit error
-            this.output.emit('error', err);
         });
         this.cache.once('close', () => {
+            if (this.hasErrored) {
+                return;
+            }
             this.sendSignedOutput();
         });
         this.relaxedBody.removeAllListeners('readable');
@@ -206,7 +220,7 @@ class DKIM {
             catch (_E) {
                 // the body hash is created here, an unknown hashAlgo throws inside this timer
                 // where nothing else could catch it
-                output.emit('error', sign.unsupportedHashAlgoError(signer.hashAlgo));
+                signer.fail(sign.unsupportedHashAlgoError(signer.hashAlgo));
                 return;
             }
             if (writeValue) {

node_modules/nodemailer/dist/esm/dkim/message-parser.js

@@ -105,7 +105,7 @@ class MessageParser extends Transform {
                 const chunk = data.slice(headerPos);
                 this.bodySize += chunk.length;
                 // this would be the first chunk of data sent downstream
-                setImmediate(() => this.push(chunk));
+                this.push(chunk);
             }
             return false;
         }
@@ -134,7 +134,7 @@ class MessageParser extends Transform {
             this.bodySize += chunk.length;
             this.push(chunk);
         }
-        setImmediate(callback);
+        callback();
     }
     /** @internal */
     _flush(callback) {

node_modules/nodemailer/dist/esm/errors.d.ts

@@ -61,6 +61,19 @@ export declare const EPROXY = "EPROXY";
 export declare const EFILEACCESS = "EFILEACCESS";
 export declare const EURLACCESS = "EURLACCESS";
 export declare const EFETCH = "EFETCH";
+/**
+ * Tells whether the error ended the connection rather than rejected what was sent over it
+ */
+export declare const isTransientError: (err: {
+    code?: string | undefined;
+    responseCode?: number | undefined;
+}) => boolean;
+/**
+ * Code Node.js sets on an error when its permission model (`--permission`) denies an
+ * operation. It is not replaced with the Nodemailer code of the failing step (`ESOCKET`,
+ * `EDNS`, `EFETCH`, ...), so a missing grant such as `--allow-net` stays recognizable.
+ */
+export declare const ERR_ACCESS_DENIED = "ERR_ACCESS_DENIED";
 /**
  * An Error together with the properties Nodemailer attaches to the errors it
  * hands to callers. Every property is optional, the set that is present
@@ -84,6 +97,10 @@ export interface NodemailerError extends NodeJS.ErrnoException {
     rejected?: string[] | undefined;
     /** Per-recipient errors for the rejected addresses */
     rejectedErrors?: NodemailerError[] | undefined;
+    /** The code the error had before Nodemailer set its own, such as ECONNREFUSED for an ESOCKET error */
+    originalCode?: string | undefined;
+    /** Which wait an ETIMEDOUT error ended: connecting, the greeting, a TLS upgrade or an idle socket */
+    timeoutType?: 'CONNECT_TIMEOUT' | 'GREETING_TIMEOUT' | 'UPGRADE_TIMEOUT' | 'SOCKET_TIMEOUT' | undefined;
 }
 /**
  * Node style callback: called with an error, or with null and the result

node_modules/nodemailer/dist/esm/errors.js

@@ -65,3 +65,13 @@ export const EPROXY = 'EPROXY';
 export const EFILEACCESS = 'EFILEACCESS';
 export const EURLACCESS = 'EURLACCESS';
 export const EFETCH = 'EFETCH';
+/**
+ * Tells whether the error ended the connection rather than rejected what was sent over it
+ */
+export const isTransientError = (err) => err.responseCode === 421 || err.code === ECONNECTION || err.code === ESOCKET || err.code === ETIMEDOUT;
+/**
+ * Code Node.js sets on an error when its permission model (`--permission`) denies an
+ * operation. It is not replaced with the Nodemailer code of the failing step (`ESOCKET`,
+ * `EDNS`, `EFETCH`, ...), so a missing grant such as `--allow-net` stays recognizable.
+ */
+export const ERR_ACCESS_DENIED = 'ERR_ACCESS_DENIED';

node_modules/nodemailer/dist/esm/fetch/cookies.js

@@ -92,19 +92,31 @@ class Cookies {
      */
     parse(cookieStr) {
         const cookie = {};
+        let hasNameValue = false;
         (cookieStr || '')
             .toString()
             .split(';')
             .forEach(cookiePart => {
-            const valueParts = cookiePart.split('=');
+            if (!cookiePart.trim()) {
-            const key = valueParts.shift().trim().toLowerCase();
-            let value = valueParts.join('=').trim();
-            let domain;
-            if (!key) {
                 // skip empty parts
                 return;
             }
-            switch (key) {
+            const valueParts = cookiePart.split('=');
+            const name = valueParts.shift().trim();
+            let value = valueParts.join('=').trim();
+            let domain;
+            // the first part is always the name-value pair, so a cookie named
+            // like an attribute is not mistaken for one (RFC 6265 section 5.2)
+            if (!hasNameValue) {
+                hasNameValue = true;
+                if (name) {
+                    // cookie names are case-sensitive, only attribute names are not
+                    cookie.name = name;
+                    cookie.value = value;
+                }
+                return;
+            }
+            switch (name.toLowerCase()) {
                 case 'expires': {
                     const expires = new Date(value);
                     // ignore date if can not parse it
@@ -132,11 +144,6 @@ class Cookies {
                 case 'httponly':
                     cookie.httponly = true;
                     break;
-                default:
-                    if (!cookie.name) {
-                        cookie.name = key;
-                        cookie.value = value;
-                    }
             }
         });
         return cookie;

node_modules/nodemailer/dist/esm/fetch/index.js

@@ -43,6 +43,17 @@ const TLS_OPTION_KEYS = [
     'sessionIdContext',
     'sigalgs'
 ];
+/**
+ * Marks an error of the request as a fetch error, unless it is a permission model
+ * denial, which keeps its own code (see ERR_ACCESS_DENIED)
+ *
+ * @param err Error to mark
+ */
+function setFetchCode(err) {
+    if (err.code !== errors.ERR_ACCESS_DENIED) {
+        err.code = errors.EFETCH;
+    }
+}
 /**
  * Resolves a URL only if it is one this module is willing to request.
  *
@@ -139,7 +150,7 @@ function nmfetch(url, options) {
                     return;
                 }
                 finished = true;
-                err.code = errors.EFETCH;
+                setFetchCode(err);
                 err.sourceUrl = url;
                 fetchRes.emit('error', err);
             });
@@ -212,7 +223,7 @@ function nmfetch(url, options) {
     catch (E) {
         finished = true;
         setImmediate(() => {
-            E.code = errors.EFETCH;
+            setFetchCode(E);
             E.sourceUrl = url;
             fetchRes.emit('error', E);
         });
@@ -224,7 +235,7 @@ function nmfetch(url, options) {
             return;
         }
         finished = true;
-        err.code = errors.EFETCH;
+        setFetchCode(err);
         err.sourceUrl = sourceUrl;
         fetchRes.emit('error', err);
         req.abort();
@@ -234,6 +245,15 @@ function nmfetch(url, options) {
         req.setTimeout(timeout, () => fail(new Error('Request Timeout')));
     }
     req.on('error', (err) => fail(err));
+    // a consumer that destroys the response stream before it ended does not want the rest of
+    // the body, release the request now instead of when the timeout fires
+    fetchRes.once('close', () => {
+        if (finished || fetchRes.readableEnded) {
+            return;
+        }
+        finished = true;
+        req.destroy();
+    });
     req.on('response', res => {
         let inflate;
         if (finished) {

node_modules/nodemailer/dist/esm/mailer/index.js

@@ -119,6 +119,11 @@ class Mail extends EventEmitter {
             this.getSocket = false;
         }
         const mail = new MailMessage(this, data);
+        // a failed message is not going to be read anymore, release its content streams
+        const fail = (err) => {
+            mail.releaseStreams();
+            done(err);
+        };
         this.logger.debug({
             tnx: 'transport',
             name: this.transporter.name,
@@ -132,7 +137,7 @@ class Mail extends EventEmitter {
                     tnx: 'plugin',
                     action: 'compile'
                 }, 'PluginCompile Error: %s', err.message);
-                return done(err);
+                return fail(err);
             }
             let recipientCount;
             try {
@@ -149,7 +154,7 @@ class Mail extends EventEmitter {
                     tnx: 'transport',
                     action: 'send'
                 }, 'Compile Error: %s', err.message);
-                return done(err);
+                return fail(err);
             }
             const maxRecipients = mail.data.maxRecipients === undefined ? DEFAULT_MAX_RECIPIENTS : mail.data.maxRecipients;
             if (maxRecipients && recipientCount > maxRecipients) {
@@ -160,7 +165,7 @@ class Mail extends EventEmitter {
                     tnx: 'transport',
                     action: 'send'
                 }, 'Send Error: %s', err.message);
-                return done(err);
+                return fail(err);
             }
             this._processPlugins('stream', mail, err => {
                 if (err) {
@@ -169,7 +174,7 @@ class Mail extends EventEmitter {
                         tnx: 'plugin',
                         action: 'stream'
                     }, 'PluginStream Error: %s', err.message);
-                    return done(err);
+                    return fail(err);
                 }
                 if (mail.data.dkim || this.dkim) {
                     mail.message.processFunc(input => {
@@ -184,6 +189,7 @@ class Mail extends EventEmitter {
                 }
                 this.transporter.send(mail, (...args) => {
                     if (args[0]) {
+                        mail.releaseStreams();
                         this.logger.error({
                             err: args[0],
                             tnx: 'transport',
@@ -251,6 +257,11 @@ class Mail extends EventEmitter {
         // setup socket handler for the mailer object
         this.getSocket = (options, callback) => {
             const protocol = proxy.protocol.replace(/:$/, '').toLowerCase();
+            // The proxy handshake is a part of connecting and draws from the same deadline as the
+            // SMTP connection that follows it: whatever the proxy takes, the connection does not get
+            const configuredTimeout = Number(this.options.connectionTimeout) || 0;
+            const connectStartedAt = Number(options.connectStartedAt) || Date.now();
+            const connectionTimeout = configuredTimeout ? Math.max(connectStartedAt + configuredTimeout - Date.now(), 1) : undefined;
             if (this.meta.has('proxy_handler_' + protocol)) {
                 return this.meta.get('proxy_handler_' + protocol)(proxy, options, callback);
             }
@@ -258,7 +269,7 @@ class Mail extends EventEmitter {
                 // Connect using a HTTP CONNECT method
                 case 'http':
                 case 'https':
-                    httpProxyClient(proxy.href, options.port, options.host, this.options.tls || {}, (err, socket) => {
+                    httpProxyClient(proxy.href, options.port, options.host, connectionTimeout ? Object.assign({}, this.options.tls, { timeout: connectionTimeout }) : this.options.tls || {}, (err, socket) => {
                         if (err) {
                             return callback(err);
                         }
@@ -292,6 +303,9 @@ class Mail extends EventEmitter {
                             },
                             command: 'connect'
                         };
+                        if (connectionTimeout) {
+                            connectionOpts.timeout = connectionTimeout;
+                        }
                         if (proxy.username || proxy.password) {
                             const username = proxy.username || '';
                             const password = proxy.password || '';
@@ -321,11 +335,13 @@ class Mail extends EventEmitter {
                     if (net.isIP(proxy.hostname)) {
                         return connect(proxy.hostname);
                     }
-                    return dns.resolve(proxy.hostname, (err, address) => {
+                    // lookup goes through the hosts file and returns an IPv6 address as well,
+                    // the same way a connection to the proxy host would be resolved otherwise
+                    return dns.lookup(proxy.hostname, (err, address) => {
                         if (err) {
                             return callback(err);
                         }
-                        connect(Array.isArray(address) ? address[0] : address);
+                        connect(address);
                     });
                 }
             }

node_modules/nodemailer/dist/esm/mailer/mail-message.d.ts

@@ -90,6 +90,11 @@ export default class MailMessage<T = SentMessageInfo> {
         [key: string]: any;
     }, key: string | number, options?: ResolveContentOptions | false): Promise<any>;
     resolveAll(callback: MailMessageDataCallback): void;
+    /**
+     * Destroys the content streams of the message once sending failed. A stream that was not
+     * read to the end would otherwise keep the file or the socket behind it open
+     */
+    releaseStreams(): void;
     normalize(callback: MailMessageDataCallback): void;
     setMailerHeader(): void;
     setPriorityHeaders(): void;

node_modules/nodemailer/dist/esm/mailer/mail-message.js

@@ -136,6 +136,26 @@ export default class MailMessage {
         };
         setImmediate(() => resolveNext());
     }
+    /**
+     * Destroys the content streams of the message once sending failed. A stream that was not
+     * read to the end would otherwise keep the file or the socket behind it open
+     */
+    releaseStreams() {
+        const data = this.data;
+        const values = [data.html, data.text, data.watchHtml, data.amp, data.raw, data.icalEvent];
+        for (const key of ['attachments', 'alternatives']) {
+            if (Array.isArray(data[key])) {
+                values.push(...data[key]);
+            }
+        }
+        for (const value of values) {
+            if (value && typeof value === 'object') {
+                shared.destroyStream(value);
+                shared.destroyStream(value.content);
+                shared.destroyStream(value.raw);
+            }
+        }
+    }
     normalize(callback) {
         const envelope = this.message.getEnvelope();
         const messageId = this.message.messageId();

node_modules/nodemailer/dist/esm/mime-node/index.d.ts

@@ -181,7 +181,7 @@ declare class MimeNode {
     childNodes: MimeNode[];
     /** Filename for this node. Useful with attachments */
     filename?: string | undefined;
-    /** Body content, or the error a content stream emitted before it was read */
+    /** Body content */
     content?: MimeNodeContent | Error | undefined;
     /** Lowercase content type, set when the headers are built */
     contentType?: string | undefined;

node_modules/nodemailer/dist/esm/mime-node/index.js

@@ -2,7 +2,7 @@
 import crypto from 'node:crypto';
 import fs from 'node:fs';
 import * as punycode from '../punycode/index.js';
-import { PassThrough } from 'node:stream';
+import { PassThrough, finished, pipeline } from 'node:stream';
 import * as shared from '../shared/index.js';
 import urlModule from 'node:url';
 import * as mimeFuncs from '../mime-funcs/index.js';
@@ -33,6 +33,14 @@ const PLAIN_ADDRESS = /^[^\s"(),:;<>@[\\\]]+@[^\s"(),:;<>@[\\\]]+$/;
 // unroutable garbage into mail for a domain the sender never named. None of these
 // characters are legal in a domain, so keep them away from the mapper.
 const URL_PARSER_UNSAFE = /[/\\?#%\x00-\x20\x7F]/;
+// pipeline() needs a callback to not throw, the errors it sees reach the last stream anyway
+const PIPELINE_NOOP = () => false;
+// The error a node streaming into an output that was destroyed stops with
+function abortedError() {
+    const err = new Error('Message stream was closed before the message was generated');
+    err.code = errors.ESTREAM;
+    return err;
+}
 /**
  * Encodes a domain the way browsers, the WHATWG URL Standard and DNS facing resolvers do,
  * which is with UTS-46 mapping applied before the Punycode step.
@@ -52,9 +60,14 @@ const URL_PARSER_UNSAFE = /[/\\?#%\x00-\x20\x7F]/;
  */
 function normalizeDomain(domain, toUnicode) {
     // domainToASCII and domainToUnicode landed in Node 7, the bundled codec covers Node 6
-    const mapper = toUnicode ? urlModule.domainToUnicode : urlModule.domainToASCII;
+    if (typeof urlModule.domainToASCII === 'function' &&
-    if (typeof mapper === 'function' && !URL_PARSER_UNSAFE.test(domain)) {
+        typeof urlModule.domainToUnicode === 'function' &&
-        const mapped = mapper(domain);
+        !URL_PARSER_UNSAFE.test(domain)) {
+        // The U-label form is decoded from the A-label form rather than from the input:
+        // Deno's domainToASCII returns an empty string for a label it cannot decode, while
+        // its domainToUnicode returns the label with U+FFFD in place of the bad part
+        const ascii = urlModule.domainToASCII(domain);
+        const mapped = ascii && toUnicode ? urlModule.domainToUnicode(ascii) : ascii;
         if (mapped) {
             return mapped;
         }
@@ -406,11 +419,7 @@ class MimeNode {
         if (typeof this.content.pipe === 'function') {
             // pre-stream handler. might be triggered if a stream is set as content
             // and 'error' fires before anything is done with this stream
-            this._contentErrorHandler = err => {
+            shared.recordStreamErrors(this.content);
-                this.content.removeListener('error', this._contentErrorHandler);
-                this.content = err;
-            };
-            this.content.once('error', this._contentErrorHandler);
         }
         else if (typeof this.content === 'string') {
             this._isPlainText = mimeFuncs.isPlainText(this.content);
@@ -622,40 +631,45 @@ class MimeNode {
     createReadStream(options) {
         options = options || {};
         const stream = new PassThrough(options);
-        let outputStream = stream;
-        let transform;
         this.stream(stream, options, err => {
             if (err) {
-                outputStream.emit('error', err);
+                stream.destroy(err);
                 return;
             }
             stream.end();
         });
-        for (let i = 0, len = this._transforms.length; i < len; i++) {
+        // the content streams of the nodes the message did not get to are not going to be read
-            transform =
+        stream.once('close', () => {
-                typeof this._transforms[i] === 'function' ? this._transforms[i]() : this._transforms[i];
+            if (!stream.writableFinished) {
-            outputStream.once('error', err => {
+                this._destroyContentStreams();
-                transform.emit('error', err);
+            }
         });
-            outputStream = outputStream.pipe(transform);
+        // The stages are joined with pipeline, which destroys all of them when any one fails
+        // or is destroyed. An error anywhere reaches the returned stream exactly once, and a
+        // consumer that destroys the returned stream stops the tree from reading its sources
+        const stages = [stream];
+        for (const transform of this._transforms) {
+            stages.push(typeof transform === 'function' ? transform() : transform);
         }
         // ensure terminating newline after possible user transforms
-        transform = new LastNewline();
+        stages.push(new LastNewline());
-        outputStream.once('error', err => {
+        let outputStream = pipeline(stages, PIPELINE_NOOP);
-            transform.emit('error', err);
+        // dkim and stuff. A process function reads its input itself and reports the errors of
+        // that input on its output, so only a consumer abort has to be carried back upstream
+        for (const processFunc of this._processFuncs) {
+            const input = outputStream;
+            outputStream = processFunc(input);
+            if (outputStream !== input) {
+                finished(outputStream, err => {
+                    if (err) {
+                        input.destroy();
+                    }
                 });
-        outputStream = outputStream.pipe(transform);
+            }
-        // dkim and stuff
-        for (let i = 0, len = this._processFuncs.length; i < len; i++) {
-            transform = this._processFuncs[i];
-            outputStream = transform(outputStream);
         }
         if (this.newline) {
             const winbreak = ['win', 'windows', 'dos', '\r\n'].includes(this.newline.toString().toLowerCase());
-            const newlineTransform = winbreak ? new LeWindows() : new LeUnix();
+            outputStream = pipeline(outputStream, winbreak ? new LeWindows() : new LeUnix(), PIPELINE_NOOP);
-            const stream = outputStream.pipe(newlineTransform);
-            outputStream.on('error', err => stream.emit('error', err));
-            return stream;
         }
         return outputStream;
     }
@@ -681,8 +695,10 @@ class MimeNode {
     }
     stream(outputStream, options, done) {
         const transferEncoding = this.getTransferEncoding();
-        let contentStream;
+        // the streams this node is reading from. A consumer that goes away mid-message destroys
-        let localStream;
+        // the output, and these are released with it instead of staying paused with a file or a
+        // socket open behind them
+        let activeStreams = [];
         // protect actual callback against multiple triggering
         let returned = false;
         const callback = (err) => {
@@ -690,13 +706,39 @@ class MimeNode {
                 return;
             }
             returned = true;
+            outputStream.removeListener('close', onOutputClose);
             done(err);
         };
+        function onOutputClose() {
+            for (const stream of activeStreams) {
+                stream.destroy();
+            }
+            return callback(abortedError());
+        }
+        // reads the streams into the output. The listener is only attached while the node reads
+        // something, a deeply nested tree would otherwise stack one per level on the output
+        const readInto = (...streams) => {
+            if (!activeStreams.length) {
+                outputStream.once('close', onOutputClose);
+            }
+            activeStreams = streams;
+        };
+        // stops here if the output was destroyed in the meantime
+        const aborted = () => {
+            if (outputStream.destroyed) {
+                callback(abortedError());
+                return true;
+            }
+            return false;
+        };
         // for multipart nodes, push child nodes
         // for content nodes end the stream
         const finalize = () => {
             let childId = 0;
             const processChildNode = () => {
+                if (aborted()) {
+                    return;
+                }
                 if (childId >= this.childNodes.length) {
                     outputStream.write('\r\n--' + this.boundary + '--\r\n');
                     return callback();
@@ -719,89 +761,80 @@ class MimeNode {
         };
         // pushes node content
         const sendContent = () => {
-            if (this.content) {
+            if (aborted()) {
-                if (Object.prototype.toString.call(this.content) === '[object Error]') {
+                return;
-                    // content is already errored
-                    return callback(this.content);
             }
-                if (typeof this.content.pipe === 'function') {
+            if (!this.content) {
-                    this.content.removeListener('error', this._contentErrorHandler);
+                return setImmediate(finalize);
-                    this._contentErrorHandler = err => callback(err);
-                    this.content.once('error', this._contentErrorHandler);
             }
             const createStream = () => {
+                if (aborted()) {
+                    return;
+                }
+                const contentError = this._takeStreamContent(this.content);
+                if (contentError) {
+                    return callback(contentError);
+                }
+                const localStream = this._getStream(this.content);
                 if (['quoted-printable', 'base64'].includes(transferEncoding)) {
-                        contentStream = new (transferEncoding === 'base64' ? base64 : qp).Encoder(options);
+                    const contentStream = transferEncoding === 'base64'
+                        ? new base64.Encoder(options)
+                        : // outside of text a lone CR or LF is data, encoding it keeps it from being
+                            // turned into a line break by a newline transform or the receiving side
+                            new qp.Encoder(Object.assign({}, options, { binary: !/^text\//i.test(this.contentType || '') }));
+                    readInto(localStream, contentStream);
                     contentStream.pipe(outputStream, {
                         end: false
                     });
-                        contentStream.once('end', finalize);
+                    // pipeline reports errors and tears both streams down. It calls back once the
-                        contentStream.once('error', err => callback(err));
+                    // encoder took all of its input, the encoded output may still be waiting to
-                        localStream = this._getStream(this.content);
+                    // be read, so the node is only done once the encoder's readable side ended
-                        localStream.pipe(contentStream);
+                    pipeline(localStream, contentStream, err => err && callback(err));
+                    finished(contentStream, { writable: false }, err => (err ? callback(err) : finalize()));
                 }
                 else {
                     // anything that is not QP or Base54 passes as-is
-                        localStream = this._getStream(this.content);
+                    readInto(localStream);
                     localStream.pipe(outputStream, {
                         end: false
                     });
-                        localStream.once('end', finalize);
+                    finished(localStream, { writable: false }, err => (err ? callback(err) : finalize()));
                 }
-                    localStream.once('error', err => callback(err));
             };
             if (this.content._resolve) {
-                    const chunks = [];
-                    let chunklen = 0;
-                    let returned = false;
                 const sourceStream = this._getStream(this.content);
-                    sourceStream.on('error', err => {
+                readInto(sourceStream);
+                shared.resolveStream(sourceStream, (err, value) => {
+                    if (err) {
+                        return callback(err);
+                    }
                     if (returned) {
                         return;
                     }
-                        returned = true;
-                        callback(err);
-                    });
-                    sourceStream.on('readable', () => {
-                        let chunk;
-                        while ((chunk = sourceStream.read()) !== null) {
-                            chunks.push(chunk);
-                            chunklen += chunk.length;
-                        }
-                    });
-                    sourceStream.on('end', () => {
-                        if (returned) {
-                            return;
-                        }
-                        returned = true;
                     this.content._resolve = false;
-                        this.content._resolvedValue = Buffer.concat(chunks, chunklen);
+                    this.content._resolvedValue = value;
                     setImmediate(createStream);
                 });
             }
             else {
                 setImmediate(createStream);
             }
-                return;
-            }
-            return setImmediate(finalize);
         };
         if (this._raw) {
             setImmediate(() => {
-                if (Object.prototype.toString.call(this._raw) === '[object Error]') {
+                if (aborted()) {
-                    // content is already errored
+                    return;
-                    return callback(this._raw);
                 }
-                // remove default error handler (if set)
+                const rawError = this._takeStreamContent(this._raw);
-                if (typeof this._raw.pipe === 'function') {
+                if (rawError) {
-                    this._raw.removeListener('error', this._contentErrorHandler);
+                    return callback(rawError);
                 }
                 const raw = this._getStream(this._raw);
+                readInto(raw);
                 raw.pipe(outputStream, {
                     end: false
                 });
-                raw.on('error', err => outputStream.emit('error', err));
+                finished(raw, { writable: false }, err => (err ? callback(err) : finalize()));
-                raw.on('end', finalize);
             });
         }
         else {
@@ -917,11 +950,7 @@ class MimeNode {
         if (this._raw && typeof this._raw.pipe === 'function') {
             // pre-stream handler. might be triggered if a stream is set as content
             // and 'error' fires before anything is done with this stream
-            this._contentErrorHandler = err => {
+            shared.recordStreamErrors(this._raw);
-                this._raw.removeListener('error', this._contentErrorHandler);
-                this._raw = err;
-            };
-            this._raw.once('error', this._contentErrorHandler);
         }
         return this;
     }
@@ -947,6 +976,37 @@ class MimeNode {
         }
         return false;
     }
+    /**
+     * Destroys the content streams of this node and of every node below it
+     *
+     * @internal
+     */
+    _destroyContentStreams() {
+        shared.destroyStream(this.content);
+        shared.destroyStream(this._raw);
+        for (const child of this.childNodes) {
+            child._destroyContentStreams();
+        }
+    }
+    /**
+     * Checks that a content value can still be read before the node streams it. A stream is
+     * refused once it errored, ended or was destroyed: piping it would either never finish or
+     * produce an empty body without any error
+     *
+     * @param content Node content or raw value
+     * @returns The error to stop with, or null when the content can be read
+     * @internal
+     */
+    _takeStreamContent(content) {
+        if (Object.prototype.toString.call(content) === '[object Error]') {
+            return content;
+        }
+        if (!content || typeof content.pipe !== 'function' || content._resolvedValue) {
+            // the value of a resolved stream is read from the buffered copy
+            return null;
+        }
+        return shared.unreadableStreamError(content);
+    }
     /**
      * Detects and returns handle to a stream related with the content.
      *

node_modules/nodemailer/dist/esm/nodemailer.js

@@ -9,10 +9,12 @@ import SESTransport from './ses-transport/index.js';
 import * as errors from './errors.js';
 import nmfetch from './fetch/index.js';
 import * as packageData from './package-info.js';
-const ETHEREAL_API = (process.env.ETHEREAL_API || 'https://api.nodemailer.com').replace(/\/+$/, '');
+// Read on use rather than at load, so that importing the module does not touch the
-const ETHEREAL_WEB = (process.env.ETHEREAL_WEB || 'https://ethereal.email').replace(/\/+$/, '');
+// environment (Deno refuses that without --allow-env, even for apps that never use Ethereal)
-const ETHEREAL_API_KEY = (process.env.ETHEREAL_API_KEY || '').replace(/\s*/g, '') || null;
+const etherealApi = () => (process.env.ETHEREAL_API || 'https://api.nodemailer.com').replace(/\/+$/, '');
-const ETHEREAL_CACHE = ['true', 'yes', 'y', '1'].includes((process.env.ETHEREAL_CACHE || 'yes').toString().trim().toLowerCase());
+const etherealWeb = () => (process.env.ETHEREAL_WEB || 'https://ethereal.email').replace(/\/+$/, '');
+const etherealApiKey = () => (process.env.ETHEREAL_API_KEY || '').replace(/\s*/g, '') || null;
+const etherealCache = () => ['true', 'yes', 'y', '1'].includes((process.env.ETHEREAL_CACHE || 'yes').toString().trim().toLowerCase());
 let testAccount = false;
 export function createTransport(transporter, defaults) {
     let options;
@@ -73,11 +75,11 @@ export function createTestAccount(apiUrl, callback) {
         });
     }
     const done = callback;
-    if (ETHEREAL_CACHE && testAccount) {
+    if (etherealCache() && testAccount) {
         setImmediate(() => done(null, testAccount));
         return promise;
     }
-    apiUrl = apiUrl || ETHEREAL_API;
+    apiUrl = apiUrl || etherealApi();
     const chunks = [];
     let chunklen = 0;
     const requestHeaders = {};
@@ -85,8 +87,9 @@ export function createTestAccount(apiUrl, callback) {
         requestor: packageData.name,
         version: packageData.version
     };
-    if (ETHEREAL_API_KEY) {
+    const apiKey = etherealApiKey();
-        requestHeaders.Authorization = 'Bearer ' + ETHEREAL_API_KEY;
+    if (apiKey) {
+        requestHeaders.Authorization = 'Bearer ' + apiKey;
     }
     const fetchOptions = {
         contentType: 'application/json',
@@ -154,7 +157,7 @@ export function getTestMessageUrl(info) {
         }
     }
     if (infoProps.has('STATUS') && infoProps.has('MSGID')) {
-        return ((testAccount && testAccount.web) || ETHEREAL_WEB) + '/message/' + infoProps.get('MSGID');
+        return ((testAccount && testAccount.web) || etherealWeb()) + '/message/' + infoProps.get('MSGID');
     }
     return false;
 }

node_modules/nodemailer/dist/esm/package-info.d.ts

@@ -1,3 +1,3 @@
 export declare const name = "nodemailer";
-export declare const version = "10.0.15";
+export declare const version = "10.1.0";
 export declare const homepage = "https://nodemailer.com/";

node_modules/nodemailer/dist/esm/package-info.js

@@ -1,4 +1,4 @@
 // Generated by scripts/build.js from package.json. Do not edit by hand.
 export const name = 'nodemailer';
-export const version = '10.0.15';
+export const version = '10.1.0';
 export const homepage = 'https://nodemailer.com/';

node_modules/nodemailer/dist/esm/qp/index.d.ts

@@ -14,6 +14,8 @@ export declare function wrap(str: string, lineLength?: number): string;
 export interface QPEncoderOptions {
     /** Maximum length for lines, set to false to disable wrapping */
     lineLength?: number | false | undefined;
+    /** The input is binary data: a CR or LF that is not part of a CRLF pair is encoded */
+    binary?: boolean | undefined;
 }
 /** The name @types/nodemailer used for QPEncoderOptions */
 export type EncoderOptions = QPEncoderOptions;

node_modules/nodemailer/dist/esm/qp/index.js

@@ -16,23 +16,52 @@ const QP_RANGES = [
     [0x20, 0x3c], // <SP>!"#$%&'()*+,-./0123456789:;
     [0x3e, 0x7e] // >?@ABCDEFGHIJKLMNOPQRSTUVWXYZ[\]^_`abcdefghijklmnopqrstuvwxyz{|}
 ];
-export function encode(buffer) {
+// 1 for every byte value that is written as is, see QP_RANGES
-    if (typeof buffer === 'string') {
+const QP_LITERAL = new Uint8Array(256);
-        buffer = Buffer.from(buffer, 'utf-8');
+for (let i = 0; i < 256; i++) {
+    QP_LITERAL[i] = checkRanges(i, QP_RANGES) ? 1 : 0;
 }
-    let result = '';
+const HEX_DIGITS = Buffer.from('0123456789ABCDEF', 'latin1');
-    let ord;
+const isWhitespace = (c) => c === 0x20 || c === 0x09;
-    for (let i = 0, len = buffer.length; i < len; i++) {
+export function encode(buffer) {
-        ord = buffer[i];
+    return encodeBytes(typeof buffer === 'string' ? Buffer.from(buffer, 'utf-8') : buffer);
+}
+/**
+ * Encodes bytes that may be followed by more input
+ *
+ * @param buffer Bytes to encode
+ * @param [next] The byte that follows the buffer, whitespace before it is kept literal unless it
+ *        is a line break. Without it the buffer ends the input and its trailing whitespace is encoded
+ * @param [binary] Keep only CRLF pairs literal. A lone CR or LF is data, not a line break, and
+ *        anything that rewrites line endings on the way would change it
+ * @param [previous] The byte before the buffer, for a buffer that starts with LF
+ * @returns Quoted-Printable encoded string
+ */
+function encodeBytes(buffer, next, binary, previous) {
+    const len = buffer.length;
+    // every byte takes three characters at most
+    const output = Buffer.allocUnsafe(len * 3);
+    let pos = 0;
+    for (let i = 0; i < len; i++) {
+        const ord = buffer[i];
+        const following = i + 1 < len ? buffer[i + 1] : next;
+        const lineBreakByte = binary && (ord === 0x0d || ord === 0x0a)
+            ? ord === 0x0d
+                ? following === 0x0a
+                : (i > 0 ? buffer[i - 1] : previous) === 0x0d
+            : true;
         // if the char is in allowed range, then keep as is, unless it is a WS in the end of a line
-        if (checkRanges(ord, QP_RANGES) &&
+        if (QP_LITERAL[ord] &&
-            !((ord === 0x20 || ord === 0x09) && (i === len - 1 || buffer[i + 1] === 0x0a || buffer[i + 1] === 0x0d))) {
+            lineBreakByte &&
-            result += String.fromCharCode(ord);
+            !(isWhitespace(ord) && (following === undefined || following === 0x0a || following === 0x0d))) {
+            output[pos++] = ord;
             continue;
         }
-        result += '=' + (ord < 0x10 ? '0' : '') + ord.toString(16).toUpperCase();
+        output[pos++] = 0x3d; // =
+        output[pos++] = HEX_DIGITS[Math.floor(ord / 16)];
+        output[pos++] = HEX_DIGITS[ord % 16];
     }
-    return result;
+    return output.toString('latin1', 0, pos);
 }
 /**
  * Adds soft line breaks to a Quoted-Printable string
@@ -143,6 +172,10 @@ function checkRanges(nr, ranges) {
     }
     return false;
 }
+// Input is encoded and wrapped this many bytes at a time. wrap() works on strings, and a large
+// chunk handed over at once, such as a whole Buffer attachment, would be held several times over
+// as intermediate strings
+const ENCODE_SLICE_SIZE = 64 * 1024;
 /**
  * Creates a transform stream for encoding data to Quoted-Printable encoding
  *
@@ -158,44 +191,81 @@ export class Encoder extends Transform {
             this.options.lineLength = this.options.lineLength || 76;
         }
         this._curLine = '';
+        this._remainingBytes = false;
+        this._lastByte = undefined;
         this.inputBytes = 0;
         this.outputBytes = 0;
     }
     /** @internal */
     _transform(chunk, encoding, done) {
-        let qp;
+        let buf = encoding !== 'buffer' ? Buffer.from(chunk, encoding) : chunk;
-        if (encoding !== 'buffer') {
+        if (!buf || !buf.length) {
-            chunk = Buffer.from(chunk, encoding);
-        }
-        if (!chunk || !chunk.length) {
             return done();
         }
-        this.inputBytes += chunk.length;
+        this.inputBytes += buf.length;
-        if (this.options.lineLength) {
+        if (this._remainingBytes) {
-            qp = this._curLine + encode(chunk);
+            buf = Buffer.concat([this._remainingBytes, buf], this._remainingBytes.length + buf.length);
-            qp = wrap(qp, this.options.lineLength);
+            this._remainingBytes = false;
-            qp = qp.replace(/(^|\n)([^\n]*)$/, (match, lineBreak, lastLine) => {
-                this._curLine = lastLine;
-                return lineBreak;
-            });
-            if (qp) {
-                this.outputBytes += qp.length;
-                this.push(qp);
         }
+        // Whitespace is encoded when it ends a line, and the end of the input counts as one. Hold
+        // back the whitespace a chunk ends with until it is known what follows it, so the output
+        // does not depend on where the input was split
+        let end = buf.length;
+        // a binary CR can only be written once it is known whether LF follows
+        while (end > 0 && (isWhitespace(buf[end - 1]) || (this.options.binary && buf[end - 1] === 0x0d))) {
+            end--;
         }
-        else {
+        if (buf.length - end <= ENCODE_SLICE_SIZE) {
-            qp = encode(chunk);
+            this._remainingBytes = end < buf.length ? Buffer.from(buf.subarray(end)) : false;
-            this.outputBytes += qp.length;
+            buf = buf.subarray(0, end);
-            this.push(qp, 'ascii');
         }
+        this._encodeSlices(buf);
         done();
     }
     /** @internal */
     _flush(done) {
+        if (this._remainingBytes) {
+            this._encodeSlices(this._remainingBytes);
+            this._remainingBytes = false;
+        }
         if (this._curLine) {
             this.outputBytes += this._curLine.length;
             this.push(this._curLine, 'ascii');
+            this._curLine = '';
         }
         done();
     }
+    /**
+     * Encodes the input in slices of ENCODE_SLICE_SIZE bytes. Each slice is told the byte that
+     * follows it, so a slice that ends in whitespace is encoded as if it was not split
+     *
+     * @internal
+     */
+    _encodeSlices(buf) {
+        for (let start = 0; start < buf.length; start += ENCODE_SLICE_SIZE) {
+            const end = Math.min(start + ENCODE_SLICE_SIZE, buf.length);
+            this._encodeSlice(buf.subarray(start, end), end < buf.length ? buf[end] : undefined);
+            this._lastByte = buf[end - 1];
+        }
+    }
+    /** @internal */
+    _encodeSlice(buf, next) {
+        let qp;
+        if (this.options.lineLength) {
+            qp = wrap(this._curLine + encodeBytes(buf, next, this.options.binary, this._lastByte), this.options.lineLength);
+            // the last line is kept until it is known whether it needs a soft break
+            const lastLF = qp.lastIndexOf('\n');
+            this._curLine = qp.substring(lastLF + 1);
+            qp = qp.substring(0, lastLF + 1);
+            if (qp) {
+                this.outputBytes += qp.length;
+                this.push(qp, 'ascii');
+            }
+        }
+        else {
+            qp = encodeBytes(buf, next, this.options.binary, this._lastByte);
+            this.outputBytes += qp.length;
+            this.push(qp, 'ascii');
+        }
+    }
 }

node_modules/nodemailer/dist/esm/sendmail-transport/index.js

@@ -1,9 +1,12 @@
 import { spawn } from 'node:child_process';
+import { pipeline } from 'node:stream';
 import * as packageData from '../package-info.js';
 import * as shared from '../shared/index.js';
 import * as errors from '../errors.js';
 import LeWindows from '../mime-node/le-windows.js';
 import LeUnix from '../mime-node/le-unix.js';
+// how long an stdin error waits for the exit code of the process before it is reported
+const STDIN_ERROR_EXIT_WAIT = 1000;
 /**
  * Generates a Transport object for Sendmail
  *
@@ -101,37 +104,75 @@ class SendmailTransport {
             return callback(E);
         }
         if (sendmail) {
+            let stream;
+            // ended once the whole message was handed to stdin
+            const messageWritten = () => !!stream && stream.readableEnded;
+            // an EPIPE says less than the exit code that usually follows it, so it is only
+            // reported when the process exits without one
+            let stdinError = null;
+            // releases whatever the message is still being read from
+            const release = () => {
+                if (stream && !messageWritten()) {
+                    stream.destroy();
+                }
+            };
+            const fail = (err) => {
+                release();
+                callback(err);
+            };
             sendmail.on('error', err => {
                 this.logger.error({
                     err,
                     tnx: 'spawn',
                     messageId
                 }, 'Error occurred when sending message %s. %s', messageId, err.message);
-                callback(err);
+                fail(err);
             });
-            sendmail.once('exit', code => {
+            // 'close' follows 'exit' with the same arguments, it is only listened to in case the
-                if (!code) {
+            // process ends without an 'exit' event
+            const onExit = (code, signal) => {
+                let err = null;
+                if (code) {
+                    err = new Error(code === 127 ? 'Sendmail command not found, process exited with code ' + code : 'Sendmail exited with code ' + code);
+                }
+                else if (signal) {
+                    err = new Error('Sendmail was terminated by ' + signal);
+                }
+                else if (!messageWritten()) {
+                    // exiting with 0 before the message was written does not mean it was queued
+                    err = new Error('Sendmail exited before the message was written');
+                }
+                else if (stdinError) {
+                    err = stdinError;
+                }
+                if (!err) {
                     return callback();
                 }
-                const err = new Error(code === 127 ? 'Sendmail command not found, process exited with code ' + code : 'Sendmail exited with code ' + code);
+                err.code = err.code || errors.ESENDMAIL;
-                err.code = errors.ESENDMAIL;
                 this.logger.error({
                     err,
                     tnx: 'stdin',
                     messageId
                 }, 'Error sending message %s to sendmail. %s', messageId, err.message);
-                callback(err);
+                fail(err);
-            });
+            };
-            // the close listener is handed the exit code as its first argument, so a non-zero
+            sendmail.once('exit', onExit);
-            // code reaching it before the exit listener did counts as the error value
+            sendmail.once('close', onExit);
-            sendmail.once('close', callback);
             sendmail.stdin.on('error', err => {
                 this.logger.error({
                     err,
                     tnx: 'stdin',
                     messageId
                 }, 'Error occurred when piping message %s to sendmail. %s', messageId, err.message);
-                callback(err);
+                if (stdinError) {
+                    return;
+                }
+                stdinError = err;
+                release();
+                // a process that closed its stdin normally exits right after, with a code that
+                // tells more than the EPIPE. Report the EPIPE if it does not
+                const exitTimer = setTimeout(() => fail(err), STDIN_ERROR_EXIT_WAIT);
+                sendmail.once('exit', () => clearTimeout(exitTimer));
             });
             const recipients = [].concat(envelope.to || []);
             if (recipients.length > 3) {
@@ -142,12 +183,11 @@ class SendmailTransport {
                 messageId
             }, 'Sending message %s to <%s>', messageId, recipients.join(', '));
             const sourceStream = mail.message.createReadStream();
-            let stream = sourceStream;
+            stream = sourceStream;
             if (this.options.newline) {
                 // apply the transport-level line ending transform; the message-level
                 // `newline` option is handled by MimeNode in createReadStream()
-                stream = sourceStream.pipe(this.winbreak ? new LeWindows() : new LeUnix());
+                stream = pipeline(sourceStream, this.winbreak ? new LeWindows() : new LeUnix(), () => false);
-                sourceStream.once('error', err => stream.emit('error', err));
             }
             stream.once('error', err => {
                 this.logger.error({

node_modules/nodemailer/dist/esm/shared/index.d.ts

@@ -1,6 +1,7 @@
+import type { NodemailerError } from '../errors.js';
 import { isProtoKey, copyOwnKeys } from './objects.js';
 import os from 'node:os';
-import type { Readable } from 'node:stream';
+import { type Readable } from 'node:stream';
 import type { OutgoingHttpHeaders } from 'node:http';
 export { isProtoKey, copyOwnKeys };
 /**
@@ -258,3 +259,33 @@ export declare const assign: (...args: ({
     [key: string]: any;
 };
 export declare const encodeXText: (str: string) => string;
+/**
+ * Keeps the first error a content stream emits before it is read, so the error is reported
+ * when the stream is read instead of being thrown as unhandled. The listener stays attached
+ * for good, a stream that emits 'error' more than once never throws the later ones either
+ *
+ * @param stream Readable stream
+ */
+export declare function recordStreamErrors(stream: Readable): void;
+/**
+ * Destroys a value if it is a readable stream that was not destroyed yet
+ *
+ * @param value Any content value
+ */
+export declare function destroyStream(value: unknown): void;
+/**
+ * Tells why a stream can not be read from start to end anymore. A stream that ended or was
+ * destroyed before anyone read it would never emit 'end' to a new reader, or, when piped, would
+ * end the destination right away and turn into an empty value without any error
+ *
+ * @param stream Readable stream
+ * @returns The error the stream failed with, an ESTREAM error, or null when it can be read
+ */
+export declare function unreadableStreamError(stream: Readable): NodemailerError | null;
+/**
+ * Streams a stream value into a Buffer
+ *
+ * @param stream Readable stream
+ * @param callback Callback function with (err, value)
+ */
+export declare function resolveStream(stream: Readable, callback: (err: Error | null, value?: Buffer) => void): void;

node_modules/nodemailer/dist/esm/shared/index.js

@@ -8,6 +8,7 @@ import { isProtoKey, copyOwnKeys } from './objects.js';
 import dns from 'node:dns';
 import net from 'node:net';
 import os from 'node:os';
+import { finished } from 'node:stream';
 // re-exported for the callers that already depend on this module, see ./objects
 export { isProtoKey, copyOwnKeys };
 const DNS_TTL = 5 * 60 * 1000;
@@ -21,14 +22,24 @@ export const _resetCacheCleanup = () => {
     lastCacheCleanup = 0;
 };
 export let networkInterfaces;
+let networkInterfacesRead = false;
+// Read on first use rather than at load, so that importing the module does not ask for
+// the interface table (Deno prompts for --allow-sys on it)
+/** @internal */
+export const _readNetworkInterfaces = () => {
+    if (!networkInterfacesRead) {
+        networkInterfacesRead = true;
         try {
             networkInterfaces = os.networkInterfaces();
         }
         catch (_err) {
             // fails on some systems
         }
+    }
+    return networkInterfaces;
+};
 const isFamilySupported = (family, allowInternal) => {
-    const addresses = Object.values(networkInterfaces || {}).flat();
+    const addresses = Object.values(_readNetworkInterfaces() || {}).flat();
     if (!addresses.length) {
         // hope for the best. Runtimes without an interface table (Cloudflare
         // Workers) report an empty object rather than throwing
@@ -39,7 +50,8 @@ const isFamilySupported = (family, allowInternal) => {
 const resolve = (family, hostname, options, callback) => {
     options = options || {};
     if (!isFamilySupported(family, options.allowInternalNetworkInterfaces)) {
-        return callback(null, []);
+        callback(null, []);
+        return null;
     }
     const dnsResolver = dns.Resolver ? new dns.Resolver(options) : dns;
     dnsResolver['resolve' + family](hostname, (err, addresses) => {
@@ -58,6 +70,7 @@ const resolve = (family, hostname, options, callback) => {
         }
         return callback(null, Array.isArray(addresses) ? addresses : [].concat(addresses || []));
     });
+    return dns.Resolver ? dnsResolver : null;
 };
 export const dnsCache = new Map();
 const formatDNSValue = (value, extra) => {
@@ -121,24 +134,59 @@ export const resolveHostname = (options, callback) => {
             }));
         }
     }
-    // Resolve both IPv4 and IPv6 addresses for fallback support
+    // The timeout limits the lookup as a whole. It is also handed to the resolver, but there
+    // it applies to every query attempt on its own, and the resolver retries a few times
+    let responded = false;
+    let deadline;
+    const respond = (err, result) => {
+        if (responded) {
+            return;
+        }
+        responded = true;
+        clearTimeout(deadline);
+        callback(err, result);
+    };
+    // a stale cached value is still better than no value at all
+    const respondCached = (error) => {
+        if (!cached) {
+            return false;
+        }
+        dnsCache.set(host, {
+            value: cached.value,
+            expires: Date.now() + (options.dnsTtl || DNS_TTL)
+        });
+        respond(null, formatDNSValue(cached.value, {
+            servername,
+            cached: true,
+            error
+        }));
+        return true;
+    };
+    const resolvers = [];
+    const timeout = Number(options.timeout) || 0;
+    if (timeout > 0) {
+        deadline = setTimeout(() => {
+            for (const resolver of resolvers) {
+                if (typeof resolver.cancel === 'function') {
+                    resolver.cancel();
+                }
+            }
+            const err = new Error('DNS lookup for ' + host + ' timed out');
+            err.code = dns.TIMEOUT;
+            if (!respondCached(err)) {
+                respond(err);
+            }
+        }, timeout);
+    }
+    // Resolve both IPv4 and IPv6 addresses for fallback support, at the same time
     let ipv4Addresses = [];
     let ipv6Addresses = [];
     let ipv4Error = null;
     let ipv6Error = null;
-    resolve(4, options.host, options, (err, addresses) => {
+    let pending = 2;
-        if (err) {
+    const onResolved = () => {
-            ipv4Error = err;
+        if (--pending || responded) {
-        }
+            return;
-        else {
-            ipv4Addresses = addresses || [];
-        }
-        resolve(6, host, options, (err, addresses) => {
-            if (err) {
-                ipv6Error = err;
-            }
-            else {
-                ipv6Addresses = addresses || [];
         }
         // Combine addresses: IPv4 first, then IPv6
         const allAddresses = ipv4Addresses.concat(ipv6Addresses);
@@ -150,41 +198,23 @@ export const resolveHostname = (options, callback) => {
                 value,
                 expires: Date.now() + (options.dnsTtl || DNS_TTL)
             });
-                return callback(null, formatDNSValue(value, {
+            return respond(null, formatDNSValue(value, {
                 servername,
                 cached: false
             }));
         }
         // No addresses from resolve4/resolve6, try dns.lookup as fallback
-            if (ipv4Error && ipv6Error) {
+        if (ipv4Error && ipv6Error && respondCached(ipv4Error)) {
             // Both resolvers had errors
-                if (cached) {
+            return;
-                    dnsCache.set(host, {
-                        value: cached.value,
-                        expires: Date.now() + (options.dnsTtl || DNS_TTL)
-                    });
-                    return callback(null, formatDNSValue(cached.value, {
-                        servername,
-                        cached: true,
-                        error: ipv4Error
-                    }));
-                }
         }
         try {
             dns.lookup(host, { all: true }, (err, addresses) => {
                 if (err) {
-                        if (cached) {
+                    if (respondCached(err)) {
-                            dnsCache.set(host, {
+                        return;
-                                value: cached.value,
-                                expires: Date.now() + (options.dnsTtl || DNS_TTL)
-                            });
-                            return callback(null, formatDNSValue(cached.value, {
-                                servername,
-                                cached: true,
-                                error: err
-                            }));
                     }
-                        return callback(err);
+                    return respond(err);
                 }
                 // Get all supported addresses from dns.lookup
                 const supportedAddresses = addresses
@@ -196,7 +226,7 @@ export const resolveHostname = (options, callback) => {
                 }
                 if (!supportedAddresses.length && cached) {
                     // nothing was found, fallback to cached value
-                        return callback(null, formatDNSValue(cached.value, {
+                    return respond(null, formatDNSValue(cached.value, {
                         servername,
                         cached: true
                     }));
@@ -208,28 +238,35 @@ export const resolveHostname = (options, callback) => {
                     value,
                     expires: Date.now() + (options.dnsTtl || DNS_TTL)
                 });
-                    return callback(null, formatDNSValue(value, {
+                return respond(null, formatDNSValue(value, {
                     servername,
                     cached: false
                 }));
             });
         }
         catch (lookupErr) {
-                if (cached) {
+            if (respondCached(lookupErr)) {
-                    dnsCache.set(host, {
+                return;
-                        value: cached.value,
-                        expires: Date.now() + (options.dnsTtl || DNS_TTL)
-                    });
-                    return callback(null, formatDNSValue(cached.value, {
-                        servername,
-                        cached: true,
-                        error: lookupErr
-                    }));
             }
-                return callback(ipv4Error || ipv6Error || lookupErr);
+            return respond(ipv4Error || ipv6Error || lookupErr);
         }
+    };
+    for (const family of [4, 6]) {
+        const resolver = resolve(family, host, options, (err, addresses) => {
+            if (family === 4) {
+                ipv4Error = err;
+                ipv4Addresses = addresses || [];
+            }
+            else {
+                ipv6Error = err;
+                ipv6Addresses = addresses || [];
+            }
+            onResolved();
         });
-    });
+        if (resolver) {
+            resolvers.push(resolver);
+        }
+    }
 };
 /**
  * Parses connection url to a structured configuration object
@@ -548,43 +585,98 @@ export const encodeXText = (str) => {
     }
     return result;
 };
+// The first error a stream emitted, see recordStreamErrors
+const streamErrors = new WeakMap();
+/**
+ * Keeps the first error a content stream emits before it is read, so the error is reported
+ * when the stream is read instead of being thrown as unhandled. The listener stays attached
+ * for good, a stream that emits 'error' more than once never throws the later ones either
+ *
+ * @param stream Readable stream
+ */
+export function recordStreamErrors(stream) {
+    stream.on('error', err => {
+        if (!streamErrors.has(stream)) {
+            streamErrors.set(stream, err);
+        }
+    });
+}
+/**
+ * Destroys a value if it is a readable stream that was not destroyed yet
+ *
+ * @param value Any content value
+ */
+export function destroyStream(value) {
+    const stream = value;
+    if (stream && typeof stream.pipe === 'function' && typeof stream.destroy === 'function' && !stream.destroyed) {
+        stream.destroy();
+    }
+}
+/**
+ * Tells why a stream can not be read from start to end anymore. A stream that ended or was
+ * destroyed before anyone read it would never emit 'end' to a new reader, or, when piped, would
+ * end the destination right away and turn into an empty value without any error
+ *
+ * @param stream Readable stream
+ * @returns The error the stream failed with, an ESTREAM error, or null when it can be read
+ */
+export function unreadableStreamError(stream) {
+    const err = streamErrors.get(stream) || stream.errored;
+    if (err) {
+        return err;
+    }
+    if (stream.readableEnded || stream.destroyed) {
+        const unreadable = new Error('Content stream was already read or destroyed');
+        unreadable.code = errors.ESTREAM;
+        return unreadable;
+    }
+    return null;
+}
 /**
  * Streams a stream value into a Buffer
  *
  * @param stream Readable stream
  * @param callback Callback function with (err, value)
  */
-function resolveStream(stream, callback) {
+export function resolveStream(stream, callback) {
     let responded = false;
+    const respond = (err, value) => {
+        if (responded) {
+            return;
+        }
+        responded = true;
+        callback(err, value);
+    };
+    const unreadable = unreadableStreamError(stream);
+    if (unreadable) {
+        // absorbs a later 'error' from the stream, there is nobody left to report it to
+        stream.on('error', () => false);
+        setImmediate(() => respond(unreadable));
+        return;
+    }
     const chunks = [];
     let chunklen = 0;
-    stream.on('error', err => {
+    stream.on('data', (chunk) => {
-        if (responded) {
+        if (typeof chunk === 'string') {
-            return;
+            chunk = Buffer.from(chunk);
         }
-        responded = true;
-        callback(err);
-    });
-    stream.on('readable', () => {
-        let chunk;
-        while ((chunk = stream.read()) !== null) {
         chunks.push(chunk);
         chunklen += chunk.length;
-        }
     });
-    stream.on('end', () => {
+    // finished() also reports a stream that is destroyed before 'end', which would otherwise
-        if (responded) {
+    // leave the callback waiting forever
-            return;
+    finished(stream, { writable: false }, err => {
+        if (err) {
+            return respond(err);
         }
-        responded = true;
         let value;
         try {
             value = Buffer.concat(chunks, chunklen);
         }
         catch (E) {
-            return callback(E);
+            return respond(E);
         }
-        callback(null, value);
+        respond(null, value);
     });
 }
 /**

node_modules/nodemailer/dist/esm/smtp-connection/http-proxy-client.d.ts

@@ -9,6 +9,8 @@ import type { Callback } from '../errors.js';
 export interface HttpProxyClientOptions {
     /** Set to false to accept a proxy certificate that fails validation (e.g. self-signed) */
     rejectUnauthorized?: boolean | undefined;
+    /** Time in milliseconds the CONNECT handshake may take, defaults to httpProxyClient.timeout or 30 seconds */
+    timeout?: number | undefined;
 }
 /**
  * Receives the proxied socket once the CONNECT handshake has succeeded, or the error that prevented it
@@ -38,7 +40,7 @@ declare function httpProxyClient(proxyUrl: string, destinationPort: number | str
  */
 declare function httpProxyClient(proxyUrl: string, destinationPort: number | string, destinationHost: string, tlsOptions: HttpProxyClientOptions | undefined, callback: HttpProxyClientCallback): void;
 /**
- * Socket timeout in milliseconds while the CONNECT handshake is in progress, defaults to 30 seconds.
+ * Time in milliseconds the CONNECT handshake may take when the call does not set one, defaults to 30 seconds.
  * Settable on the function itself, the same way the CommonJS module exposed it.
  */
 declare namespace httpProxyClient {

node_modules/nodemailer/dist/esm/smtp-connection/http-proxy-client.js

@@ -8,6 +8,8 @@ import * as errors from '../errors.js';
 // Cap the CONNECT response we buffer before the header terminator, so a proxy that
 // never sends \r\n\r\n cannot grow memory unboundedly before the socket times out.
 const MAX_RESPONSE_HEADER_BYTES = 64 * 1024;
+// URL hostnames keep the brackets around an IPv6 literal, socket options and net.isIPv6 take it without
+const unbracket = (host) => typeof host === 'string' && host.startsWith('[') && host.endsWith(']') ? host.slice(1, -1) : host;
 function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions, callback) {
     if (typeof tlsOptions === 'function') {
         callback = tlsOptions;
@@ -27,6 +29,8 @@ function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions,
         return;
     }
     const proxy = urllib.parse(proxyUrl);
+    // the CONNECT request line and the Host header take an IPv6 destination in brackets
+    const authority = (net.isIPv6(unbracket(destinationHost)) ? '[' + unbracket(destinationHost) + ']' : destinationHost) + ':' + destinationPort;
     const connectOptions = {
         host: proxy.hostname,
         port: Number(proxy.port) ? Number(proxy.port) : proxy.protocol === 'https:' ? 443 : 80
@@ -42,15 +46,27 @@ function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions,
     else {
         connect = net.connect.bind(net);
     }
+    // The handshake is bounded as a whole, a proxy that keeps sending a byte now and then can
+    // not hold the connection open past it
+    const timeout = Number(tlsOptions.timeout) || httpProxyClient.timeout || 30 * 1000;
     let socket;
-    // Error harness for initial connection. Once connection is established, the responsibility
+    // Single settlement path for the handshake: every temporary listener and the timer are
-    // to handle errors is passed to whoever uses this socket
+    // dropped exactly once. Once the tunnel is up, the responsibility to handle errors is passed
+    // to whoever uses this socket
     let finished = false;
-    const tempSocketErr = (err) => {
+    let timer;
+    const cleanup = () => {
+        clearTimeout(timer);
+        socket.removeListener('data', onSocketData);
+        socket.removeListener('error', fail);
+        socket.removeListener('close', onEarlyClose);
+    };
+    function fail(err) {
         if (finished) {
             return;
         }
         finished = true;
+        cleanup();
         try {
             socket.destroy();
         }
@@ -58,44 +74,19 @@ function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions,
             // ignore
         }
         done(err);
-    };
-    const timeoutErr = () => {
-        const err = new Error('Proxy socket timed out');
-        err.code = 'ETIMEDOUT';
-        tempSocketErr(err);
-    };
-    socket = connect(connectOptions, () => {
-        if (finished) {
-            return;
     }
-        const reqHeaders = {
+    function onEarlyClose() {
-            Host: destinationHost + ':' + destinationPort,
+        const err = new Error('Proxy closed the connection before the tunnel was established');
-            Connection: 'close'
+        err.code = errors.EPROXY;
-        };
+        fail(err);
-        if (proxy.auth) {
-            reqHeaders['Proxy-Authorization'] = 'Basic ' + Buffer.from(proxy.auth).toString('base64');
     }
-        socket.write(
-        // HTTP method
-        'CONNECT ' +
-            destinationHost +
-            ':' +
-            destinationPort +
-            ' HTTP/1.1\r\n' +
-            // HTTP request headers
-            Object.keys(reqHeaders)
-                .map(key => key + ': ' + reqHeaders[key])
-                .join('\r\n') +
-            // End request
-            '\r\n\r\n');
     // The response is collected as chunks and only the bytes that just arrived, together
     // with the three before them, are searched for the end of the headers. Appending to a
     // string and searching all of it again re-read the whole response on every chunk.
     const chunks = [];
     let received = 0;
     let tail = '';
-        const onSocketData = (chunk) => {
+    function onSocketData(chunk) {
-            let match;
         if (finished) {
             return;
         }
@@ -104,46 +95,75 @@ function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions,
         chunks.push(chunk);
         received += chunk.length;
         tail = window.slice(-3);
-            if (windowEnd >= 0) {
+        if (windowEnd < 0) {
+            if (received > MAX_RESPONSE_HEADER_BYTES) {
+                const err = new Error('Proxy response headers too large');
+                err.code = errors.EPROXY;
+                fail(err);
+            }
+            return;
+        }
+        // Stop reading before anything is put back. A socket that keeps flowing would emit the
+        // bytes after the headers, a greeting the proxy sent together with its own response,
+        // before the next owner of the socket has a listener for them
         socket.removeListener('data', onSocketData);
+        socket.pause();
         const headerEnd = received - window.length + windowEnd;
-                const response = Buffer.concat(chunks, received).toString('binary');
+        const response = Buffer.concat(chunks, received);
-                const headers = response.substr(0, headerEnd);
+        if (response.length > headerEnd + 4) {
-                const remainder = response.substr(headerEnd + 4);
+            socket.unshift(response.subarray(headerEnd + 4));
-                if (remainder) {
+        }
-                    socket.unshift(Buffer.from(remainder, 'binary'));
+        // check response code
+        const match = response.toString('binary', 0, headerEnd).match(/^HTTP\/\d+\.\d+ (\d+)/i);
+        if (!match || (match[1] || '').charAt(0) !== '2') {
+            const err = new Error('Invalid response from proxy' + ((match && ': ' + match[1]) || ''));
+            err.code = errors.EPROXY;
+            return fail(err);
         }
         // proxy connection is now established
         finished = true;
-                // check response code
+        cleanup();
-                match = headers.match(/^HTTP\/\d+\.\d+ (\d+)/i);
+        // A fresh socket starts flowing once something listens for 'data', a paused one would
-                if (!match || (match[1] || '').charAt(0) !== '2') {
+        // not. Keep that behaviour for the next owner of the socket
-                    try {
+        const resumeOnData = (event) => {
-                        socket.destroy();
+            if (event === 'data') {
-                    }
+                socket.removeListener('newListener', resumeOnData);
-                    catch (_E) {
+                socket.resume();
-                        // ignore
-                    }
-                    const err = new Error('Invalid response from proxy' + ((match && ': ' + match[1]) || ''));
-                    err.code = errors.EPROXY;
-                    return done(err);
-                }
-                socket.removeListener('error', tempSocketErr);
-                socket.removeListener('timeout', timeoutErr);
-                socket.setTimeout(0);
-                return done(null, socket);
-            }
-            if (received > MAX_RESPONSE_HEADER_BYTES) {
-                socket.removeListener('data', onSocketData);
-                const err = new Error('Proxy response headers too large');
-                err.code = errors.EPROXY;
-                return tempSocketErr(err);
             }
         };
+        socket.on('newListener', resumeOnData);
+        return done(null, socket);
+    }
+    socket = connect(connectOptions, () => {
+        if (finished) {
+            return;
+        }
+        const reqHeaders = {
+            Host: authority,
+            Connection: 'close'
+        };
+        if (proxy.auth) {
+            reqHeaders['Proxy-Authorization'] = 'Basic ' + Buffer.from(proxy.auth).toString('base64');
+        }
+        socket.write(
+        // HTTP method
+        'CONNECT ' +
+            authority +
+            ' HTTP/1.1\r\n' +
+            // HTTP request headers
+            Object.keys(reqHeaders)
+                .map(key => key + ': ' + reqHeaders[key])
+                .join('\r\n') +
+            // End request
+            '\r\n\r\n');
         socket.on('data', onSocketData);
     });
-    socket.setTimeout(httpProxyClient.timeout || 30 * 1000);
+    timer = setTimeout(() => {
-    socket.on('timeout', timeoutErr);
+        const err = new Error('Proxy socket timed out');
-    socket.once('error', tempSocketErr);
+        err.code = errors.ETIMEDOUT;
+        fail(err);
+    }, timeout);
+    socket.once('error', fail);
+    socket.once('close', onEarlyClose);
 }
 export default httpProxyClient;

node_modules/nodemailer/dist/esm/smtp-connection/index.d.ts

@@ -3,7 +3,7 @@ import net from 'node:net';
 import tls from 'node:tls';
 import { type Readable } from 'node:stream';
 import * as shared from '../shared/index.js';
-import type { Callback, NodemailerError } from '../errors.js';
+import { type Callback, type NodemailerError } from '../errors.js';
 import type XOAuth2 from '../xoauth2/index.js';
 import type { XOAuth2Options } from '../xoauth2/index.js';
 /**
@@ -275,6 +275,12 @@ export interface SMTPConnectionConnectOptions extends tls.ConnectionOptions {
     allowInternalNetworkInterfaces?: boolean | undefined;
     /** DNS lookup timeout in ms */
     timeout?: number | undefined;
+    /** Try the resolved addresses in turn, see net.connect */
+    autoSelectFamily?: boolean | undefined;
+    /** Time in ms an address gets before the next one is tried, see net.connect */
+    autoSelectFamilyAttemptTimeout?: number | undefined;
+    /** Hands the resolved addresses to net.connect */
+    lookup?: net.LookupFunction | undefined;
 }
 /**
  * A queued handler for the next server response

node_modules/nodemailer/dist/esm/smtp-connection/index.js

@@ -7,12 +7,30 @@ import crypto from 'node:crypto';
 import DataStream from './data-stream.js';
 import { PassThrough } from 'node:stream';
 import * as shared from '../shared/index.js';
+import { ERR_ACCESS_DENIED, isTransientError } from '../errors.js';
 // default timeout values in ms
 const CONNECTION_TIMEOUT = 2 * 60 * 1000; // how much to wait for the connection to be established
 const SOCKET_TIMEOUT = 10 * 60 * 1000; // how much to wait for socket inactivity before disconnecting the client
 const GREETING_TIMEOUT = 30 * 1000; // how much to wait after connection is established but SMTP greeting is not receieved
 const DNS_TIMEOUT = 30 * 1000; // how much to wait for resolveHostname
+const CLOSE_TIMEOUT = 5 * 1000; // how much to wait for the server to close its side after we closed ours
+const KEEPALIVE_DELAY = 30 * 1000; // idle time before TCP keepalive probes start, keeps NAT mappings of idle connections alive
 const TEARDOWN_NOOP = () => { }; // reusable no-op handler for absorbing errors during socket teardown
+// Random order, so that connections spread over the addresses of a host
+function shuffle(list) {
+    const result = list.slice();
+    for (let i = result.length - 1; i > 0; i--) {
+        const j = Math.floor(Math.random() * (i + 1));
+        [result[i], result[j]] = [result[j], result[i]];
+    }
+    return result;
+}
+// Every timeout is reported with the ETIMEDOUT code, timeoutType tells which one it was
+function timeoutError(message, timeoutType) {
+    const err = new Error(message);
+    err.timeoutType = timeoutType;
+    return err;
+}
 // how many bytes a single server response may occupy while it is still being received.
 // Generous compared to any real reply, it only stops a peer that never completes one
 const MAX_RESPONSE_SIZE = 1024 * 1024;
@@ -135,8 +153,8 @@ class SMTPConnection extends EventEmitter {
         this._maxAllowedSize = 0;
         this._responseActions = [];
         this._recipientQueue = [];
-        this._greetingTimeout = false;
+        this._phaseTimer = false;
-        this._connectionTimeout = false;
+        this._plaintextEhlo = false;
         this._destroyed = false;
         this._closing = false;
         this._currentDataStream = false;
@@ -147,14 +165,25 @@ class SMTPConnection extends EventEmitter {
         this._onSocketClose = () => this._onClose();
         this._onSocketEnd = () => this._onEnd();
         this._onSocketTimeout = () => this._onTimeout();
-        this._onConnectionSocketError = err => this._onConnectionError(err, 'ESOCKET');
+        this._onConnectionSocketError = err => this._onError(err, 'ESOCKET', false, 'CONN');
-        this._connectionAttemptId = 0;
     }
     /**
      * Creates a connection to a SMTP server and sets up connection
      * listener
      */
     connect(connectCallback) {
+        if (this._connectCalled && !this._destroyed) {
+            // A connection is opened once. A second call would open a second socket over the
+            // first one and run the session handlers of both against the same state
+            const err = this._formatError('Cannot connect - connect() was already called for this connection', 'ECONNECTION', false, 'API');
+            if (typeof connectCallback === 'function') {
+                setImmediate(() => connectCallback(err));
+                return;
+            }
+            this.logger.warn({ tnx: 'smtp' }, '%s', err.message);
+            return;
+        }
+        this._connectCalled = true;
         if (typeof connectCallback === 'function') {
             this._connectCallback = connectCallback;
             this.once('connect', () => {
@@ -169,11 +198,15 @@ class SMTPConnection extends EventEmitter {
                 return connectCallback(this._formatError(isDestroyedMessage, 'ECONNECTION', false, 'CONN'));
             }
         }
+        // connectionTimeout covers the whole of connecting: the DNS lookup and every address tried
+        const connectionTimeout = this.options.connectionTimeout || CONNECTION_TIMEOUT;
+        // a transport that first opened a proxy connection for this one sets when that started
+        this._connectionDeadline = (this._connectStartedAt || Date.now()) + connectionTimeout;
         let opts = {
             port: this.port,
             host: this.host,
             allowInternalNetworkInterfaces: this.allowInternalNetworkInterfaces,
-            timeout: this.options.dnsTimeout || DNS_TIMEOUT
+            timeout: Math.min(this.options.dnsTimeout || DNS_TIMEOUT, connectionTimeout)
         };
         if (this.options.localAddress) {
             opts.localAddress = this.options.localAddress;
@@ -202,7 +235,6 @@ class SMTPConnection extends EventEmitter {
             return this._resolveAndConnect(opts, _resolved => {
                 try {
                     this._socket.connect(this.port, this.host, () => {
-                        this._socket.setKeepAlive(true);
                         // a `secure` connection over a caller-provided socket must still
                         // perform the TLS handshake, otherwise AUTH and the message body
                         // would be sent in cleartext despite the caller requesting TLS
@@ -234,9 +266,40 @@ class SMTPConnection extends EventEmitter {
                 }
             }
             return this._resolveAndConnect(opts, resolved => {
-                // Store fallback addresses for retry on connection failure
+                let addresses = resolved._addresses || [];
-                this._fallbackAddresses = (resolved._addresses || []).filter(addr => addr !== opts.host);
+                if (opts.localAddress) {
-                this._connectOpts = Object.assign({}, opts);
+                    // a socket bound to an address of one family can not reach the other one
+                    const localFamily = net.isIPv6(opts.localAddress) ? 6 : 4;
+                    const sameFamily = addresses.filter(addr => net.isIP(addr) === localFamily);
+                    addresses = sameFamily.length ? sameFamily : addresses;
+                }
+                if (addresses.length > 1) {
+                    // net.connect tries the addresses in turn and moves on to the next one when an
+                    // attempt fails or takes too long. With both families it starts on IPv6 and
+                    // alternates (RFC 8305), so a host with a broken IPv6 path costs a fraction of
+                    // a second instead of a whole connection timeout
+                    const ipv6 = addresses.filter(addr => net.isIPv6(addr));
+                    const ipv4 = addresses.filter(addr => !net.isIPv6(addr));
+                    const ordered = shuffle(ipv6).concat(shuffle(ipv4));
+                    opts.host = this.host;
+                    opts.autoSelectFamily = true;
+                    if (!ipv6.length || !ipv4.length) {
+                        // a slow address of the only family gets its share of the time, not the
+                        // quarter second meant for an address family that does not work
+                        const remaining = this._connectionDeadline - Date.now();
+                        opts.autoSelectFamilyAttemptTimeout = Math.max(Math.floor(remaining / ordered.length), 10);
+                    }
+                    opts.lookup = ((hostname, lookupOptions, callback) => {
+                        if (lookupOptions && lookupOptions.all) {
+                            const all = ordered.map(address => ({ address, family: net.isIPv6(address) ? 6 : 4 }));
+                            return setImmediate(() => callback(null, all));
+                        }
+                        setImmediate(() => callback(null, ordered[0], net.isIPv6(ordered[0]) ? 6 : 4));
+                    });
+                }
+                else if (addresses.length) {
+                    opts.host = addresses[0];
+                }
                 this._connectToHost(opts, this.secureConnection);
             });
         }
@@ -283,20 +346,11 @@ class SMTPConnection extends EventEmitter {
         if (this._destroyed || this._closing) {
             return;
         }
-        this._connectionAttemptId++;
-        const currentAttemptId = this._connectionAttemptId;
         const connectFn = secure
             ? tls.connect
             : net.connect;
         try {
-            this._socket = connectFn(opts, () => {
+            this._socket = connectFn(opts, () => this._onConnect());
-                // Ignore callback if this is a stale connection attempt
-                if (this._connectionAttemptId !== currentAttemptId) {
-                    return;
-                }
-                this._socket.setKeepAlive(true);
-                this._onConnect();
-            });
             this._setupConnectionHandlers();
         }
         catch (E) {
@@ -309,51 +363,37 @@ class SMTPConnection extends EventEmitter {
      * @internal
      */
     _setupConnectionHandlers() {
-        this._connectionTimeout = setTimeout(() => {
+        this._startPhase(Math.max((this._connectionDeadline || Date.now()) - Date.now(), 0), timeoutError('Connection timeout', 'CONNECT_TIMEOUT'));
-            this._onConnectionError('Connection timeout', 'ETIMEDOUT');
-        }, this.options.connectionTimeout || CONNECTION_TIMEOUT);
         this._socket.on('error', this._onConnectionSocketError);
     }
     /**
-     * Handles connection errors with fallback to alternative addresses
+     * Starts the timer of a connection phase: connecting, waiting for the greeting or a TLS
+     * upgrade. The phases follow one another, so starting one ends the one before
      *
-     * @param err Error object or message
+     * @param timeout Time the phase may take
-     * @param code Error code
+     * @param err Error to fail with when it takes longer
      * @internal
      */
-    _onConnectionError(err, code) {
+    _startPhase(timeout, err) {
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
-        // Check if we have fallback addresses to try
+        this._phaseTimer = setTimeout(() => {
-        const canFallback = this._fallbackAddresses && this._fallbackAddresses.length && this.stage === 'init' && !this._destroyed;
+            this._phaseTimer = false;
-        if (!canFallback) {
+            this._onError(err, 'ETIMEDOUT', false, 'CONN');
-            // No more fallback addresses, report the error
+        }, timeout);
-            this._onError(err, code, false, 'CONN');
-            return;
     }
-        const nextHost = this._fallbackAddresses.shift();
+    /**
-        this.logger.info({
+     * Time the greeting or a STARTTLS upgrade may take: greetingTimeout, cut short by what is left
-            tnx: 'network',
+     * of connectionTimeout
-            failedHost: this._connectOpts.host,
+     *
-            nextHost,
+     * @internal
-            error: err.message || err
+     */
-        }, 'Connection to %s failed, trying %s', this._connectOpts.host, nextHost);
+    _remainingSetupTime() {
-        // Clean up current socket
+        return Math.min(this.options.greetingTimeout || GREETING_TIMEOUT, Math.max((this._connectionDeadline || Infinity) - Date.now(), 1));
-        if (this._socket) {
-            try {
-                this._socket.removeListener('error', this._onConnectionSocketError);
-                // Absorb any late teardown error (e.g. a TLS fallback socket emitting
-                // after destroy), mirroring the guard used in close()
-                this._socket.on('error', TEARDOWN_NOOP);
-                this._socket.destroy();
     }
-            catch (_E) {
+    /** @internal */
-                // ignore
+    _clearPhase() {
-            }
+        clearTimeout(this._phaseTimer);
-            this._socket = null;
+        this._phaseTimer = false;
-        }
-        // Update host and retry
-        this._connectOpts.host = nextHost;
-        this._connectToHost(this._connectOpts, this.secureConnection);
     }
     /**
      * Sends QUIT
@@ -366,8 +406,7 @@ class SMTPConnection extends EventEmitter {
      * Closes the connection to the server
      */
     close() {
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
-        clearTimeout(this._greetingTimeout);
         this._responseActions = [];
         // allow to run this function only once
         if (this._closing) {
@@ -390,13 +429,15 @@ class SMTPConnection extends EventEmitter {
             }
             this._currentDataStream = false;
         }
-        // Detach from the message stream as well. The listener is swapped for a no-op rather than
+        // Detach from the message stream as well and release whatever it reads from, the message
-        // removed, a stream destroyed with an error later on would otherwise throw it as unhandled
+        // can not be sent over this connection anymore. The listener is swapped for a no-op rather
+        // than removed, a stream destroyed with an error would otherwise throw it as unhandled
         if (this._pendingSend) {
             const { stream, onStreamError } = this._pendingSend;
             if (stream) {
                 stream.removeListener('error', onStreamError);
                 stream.on('error', TEARDOWN_NOOP);
+                stream.destroy();
             }
             this._pendingSend = false;
         }
@@ -415,6 +456,15 @@ class SMTPConnection extends EventEmitter {
                 // sending cleartext after TLS shutdown triggers ERR_SSL_BAD_RECORD_TYPE)
                 socket.on('error', TEARDOWN_NOOP);
                 socket[closeMethod]();
+                if (closeMethod === 'end') {
+                    // end() only closes our side, a server that never closes its own would keep
+                    // the socket, and the process with it, around for good
+                    const closeTimer = setTimeout(() => socket.destroy(), CLOSE_TIMEOUT);
+                    if (typeof closeTimer.unref === 'function') {
+                        closeTimer.unref();
+                    }
+                    socket.once('close', () => clearTimeout(closeTimer));
+                }
             }
             catch (_E) {
                 // just ignore
@@ -619,14 +669,9 @@ class SMTPConnection extends EventEmitter {
         const startTime = Date.now();
         this._setEnvelope(envelope, (err, info) => {
             if (err) {
-                // create passthrough stream to consume to prevent OOM
+                // the message is not going to be sent, release whatever the stream reads from
-                const stream = new PassThrough();
+                if (typeof message.destroy === 'function') {
-                if (typeof message.pipe === 'function') {
+                    message.destroy();
-                    message.pipe(stream);
-                }
-                else {
-                    stream.write(message);
-                    stream.end();
                 }
                 return callback(err);
             }
@@ -680,7 +725,7 @@ class SMTPConnection extends EventEmitter {
      */
     _onConnect() {
         const socket = this._socket;
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
         this.logger.info({
             tnx: 'network',
             localAddress: socket.localAddress,
@@ -710,16 +755,42 @@ class SMTPConnection extends EventEmitter {
         socket.once('end', this._onSocketEnd);
         socket.setTimeout(this.options.socketTimeout || SOCKET_TIMEOUT);
         socket.on('timeout', this._onSocketTimeout);
-        this._greetingTimeout = setTimeout(() => {
+        // keepalive also covers sockets handed over by a proxy or by the caller
-            // if still waiting for greeting, give up
+        if (typeof socket.setKeepAlive === 'function') {
-            if (this._socket && !this._destroyed && this._responseActions[0] === this._actionGreeting) {
+            socket.setKeepAlive(true, KEEPALIVE_DELAY);
-                this._onError('Greeting never received', 'ETIMEDOUT', false, 'CONN');
         }
-        }, this.options.greetingTimeout || GREETING_TIMEOUT);
+        // Commands are written in the batches they belong to (see cork() for PIPELINING), Nagle
+        // would only hold a write back until the server acknowledged the previous one. Against a
+        // server that delays its ACKs that costs 40ms on every message
+        if (typeof socket.setNoDelay === 'function') {
+            socket.setNoDelay(true);
+        }
+        // bounded by greetingTimeout and by what is left of connectionTimeout, which covers setting
+        // the session up from the DNS lookup to the end of a STARTTLS upgrade
+        this._startPhase(this._remainingSetupTime(), timeoutError('Greeting never received', 'GREETING_TIMEOUT'));
         this._responseActions.push(this._actionGreeting);
         // we have a 'data' listener set up so resume socket if it was paused
         socket.resume();
     }
+    /**
+     * Ends the session after a 421 reply. The replies queued for commands sent along with the
+     * answered one are not going to come, so the message in flight is failed here
+     *
+     * @param str The 421 reply
+     * @internal
+     */
+    _onServerClosing(str) {
+        if (this._destroyed) {
+            return;
+        }
+        const pendingSend = this._pendingSend;
+        const envelope = this._envelope;
+        this._responseActions = [];
+        this.close();
+        if (pendingSend) {
+            pendingSend.callback((envelope && envelope.mailError) || this._formatError('Server closed the connection', 'ECONNECTION', str, 'CONN'));
+        }
+    }
     /**
      * 'data' listener for data coming from the server
      *
@@ -794,8 +865,7 @@ class SMTPConnection extends EventEmitter {
      * @internal
      */
     _onError(err, type, data, command) {
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
-        clearTimeout(this._greetingTimeout);
         if (this._destroyed) {
             // just ignore, already closed
             // this might happen when a socket is canceled because of reached timeout
@@ -803,12 +873,12 @@ class SMTPConnection extends EventEmitter {
             return;
         }
         err = this._formatError(err, type, data, command);
-        const transientCodes = ['ETIMEDOUT', 'ESOCKET', 'ECONNECTION'];
+        // the message carries the server response, it is an argument and not the format string
-        if (transientCodes.includes(err.code)) {
+        if (isTransientError(err)) {
-            this.logger.warn(data, err.message);
+            this.logger.warn({ tnx: 'smtp', err }, '%s', err.message);
         }
         else {
-            this.logger.error(data, err.message);
+            this.logger.error({ tnx: 'smtp', err }, '%s', err.message);
         }
         // close() forgets the send in flight, it is completed with this same error afterwards so
         // a late message stream error has nothing left to report
@@ -828,7 +898,12 @@ class SMTPConnection extends EventEmitter {
         else {
             err = new Error(message);
         }
-        if (type && type !== 'Error') {
+        // a permission model denial keeps its own code, see ERR_ACCESS_DENIED
+        if (type && type !== 'Error' && err.code !== ERR_ACCESS_DENIED) {
+            // the code of a system error, such as ECONNREFUSED, still tells what happened
+            if (err.code && err.code !== type && !err.originalCode) {
+                err.originalCode = err.code;
+            }
             err.code = type;
         }
         if (response) {
@@ -880,6 +955,19 @@ class SMTPConnection extends EventEmitter {
             this.close();
             return;
         }
+        if (!failureResponse &&
+            this.stage === 'connected' &&
+            !this._responseActions.length &&
+            !this._pendingSend &&
+            !this._destroyed &&
+            !this._closing) {
+            // nothing was waiting for the server, so this is the server ending an idle session
+            // (usually after its idle timeout), not a failure
+            this.logger.info({
+                tnx: 'network'
+            }, 'Server closed the idle connection');
+            return this._destroy();
+        }
         if (failureResponse || (this._responseActions[0] !== this.close && !this._destroyed)) {
             return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', failureResponse, 'CONN');
         }
@@ -905,7 +993,7 @@ class SMTPConnection extends EventEmitter {
      * @internal
      */
     _onTimeout() {
-        return this._onError(new Error('Timeout'), 'ETIMEDOUT', false, 'CONN');
+        return this._onError(timeoutError('Timeout', 'SOCKET_TIMEOUT'), 'ETIMEDOUT', false, 'CONN');
     }
     /**
      * Destroys the client, emits 'end'
@@ -920,10 +1008,7 @@ class SMTPConnection extends EventEmitter {
         this.destroyed = true;
         // a connection the server dropped before the greeting would otherwise keep
         // the greeting timer, and with it the process, alive until it fires
-        clearTimeout(this._connectionTimeout);
+        this._clearPhase();
-        clearTimeout(this._greetingTimeout);
-        this._connectionTimeout = false;
-        this._greetingTimeout = false;
         this.emit('end');
     }
     /**
@@ -940,6 +1025,15 @@ class SMTPConnection extends EventEmitter {
         // inject plaintext bytes after the "220" reply (e.g. a CRLF-free fragment that
         // would otherwise be prepended to the first post-TLS response and parsed as
         // part of the secured EHLO capabilities). STARTTLS response injection.
+        const discarded = this._remainder.length + this._responseQueue.reduce((total, response) => total + response.length, 0);
+        if (discarded) {
+            // a server does not send anything here on its own, this is worth knowing about
+            this.logger.warn({
+                tnx: 'smtp',
+                discarded
+            }, 'Discarded %s bytes received in plaintext after the STARTTLS response', discarded);
+        }
+        this._plaintextEhlo = false;
         this._remainder = '';
         this._responseQueue = [];
         this._responsePartial = false;
@@ -949,6 +1043,7 @@ class SMTPConnection extends EventEmitter {
         const socketPlain = this._socket;
         socketPlain.removeListener('data', this._onSocketData); // incoming data is going to be gibberish from this point onwards
         socketPlain.removeListener('timeout', this._onSocketTimeout); // timeout will be re-set for the new socket object
+        socketPlain.setTimeout(0);
         const opts = Object.assign({
             socket: socketPlain,
             host: this.host
@@ -969,9 +1064,14 @@ class SMTPConnection extends EventEmitter {
             socketPlain.removeListener('error', this._onConnectionSocketError);
         };
         this.upgrading = true;
+        // the socket timeout only notices a server that sends nothing at all, a handshake that
+        // trickles along would otherwise hold the connection for as long as the server likes
+        // STARTTLS is the last step of setting the session up
+        this._startPhase(this._remainingSetupTime(), timeoutError('TLS handshake timed out', 'UPGRADE_TIMEOUT'));
         // tls.connect is not an asynchronous function however it may still throw errors and requires to be wrapped with try/catch
         try {
             this._socket = tls.connect(opts, () => {
+                this._clearPhase();
                 this.secure = true;
                 this.upgrading = false;
                 this._socket.on('data', this._onSocketData);
@@ -980,6 +1080,7 @@ class SMTPConnection extends EventEmitter {
             });
         }
         catch (err) {
+            this._clearPhase();
             removePlainSocketListeners();
             return callback(err);
         }
@@ -1020,10 +1121,24 @@ class SMTPConnection extends EventEmitter {
             }, str.replace(/\r?\n$/, ''));
         }
         const action = this._responseActions.shift();
+        // RFC 5321 4.2: 421 means the server is about to close the connection, whatever it answers
+        const closing = /^421[ -]/.test(str);
         if (typeof action === 'function') {
+            // the command gets its own error first, the code tells which step failed
             action.call(this, str);
+            if (closing) {
+                return this._onServerClosing(str);
+            }
             setImmediate(() => this._processResponse());
         }
+        else if (closing && !this._pendingSend && this.stage === 'connected') {
+            // RFC 5321 4.2: a server may send 421 at any time when it is about to close the
+            // connection. Nothing was waiting for a reply, so this ends an idle session
+            this.logger.info({
+                tnx: 'smtp'
+            }, 'Server closed the idle connection: %s', str);
+            this.close();
+        }
         else {
             return this._onError(new Error('Unexpected Response'), 'EPROTOCOL', str, 'CONN');
         }
@@ -1118,6 +1233,9 @@ class SMTPConnection extends EventEmitter {
                 return callback(this._formatError('Server does not support REQUIRETLS extension (RFC 8689)', 'EREQUIRETLS', false, 'MAIL FROM'));
             }
         }
+        // RFC 2920: with PIPELINING the whole envelope and DATA go out without waiting for the
+        // replies in between, which saves two round trips for every message
+        this._envelope.pipelined = this._supportedExtensions.includes('PIPELINING');
         this._responseActions.push(str => {
             this._actionMAIL(str, callback);
         });
@@ -1155,7 +1273,38 @@ class SMTPConnection extends EventEmitter {
         if (this._envelope.requireTLSExtensionEnabled) {
             args.push('REQUIRETLS');
         }
-        this._sendCommand('MAIL FROM:<' + this._envelope.from + '>' + (args.length ? ' ' + args.join(' ') : ''));
+        const mailFrom = 'MAIL FROM:<' + this._envelope.from + '>' + (args.length ? ' ' + args.join(' ') : '');
+        this._recipientQueue = [];
+        if (!this._envelope.pipelined) {
+            this._sendCommand(mailFrom);
+            return;
+        }
+        // corked, so the batch leaves in one segment instead of the first command alone
+        const socket = this._socket;
+        socket.cork();
+        this._sendCommand(mailFrom);
+        while (this._envelope.rcptQueue.length) {
+            this._sendRcpt(this._envelope.rcptQueue.shift(), callback);
+        }
+        this._responseActions.push(str => {
+            this._actionDATA(str, callback);
+        });
+        this._sendCommand('DATA');
+        socket.uncork();
+    }
+    /**
+     * Sends RCPT TO for a recipient and queues the handler for the reply
+     *
+     * @param recipient Recipient address
+     * @param callback Callback to run once the envelope is processed
+     * @internal
+     */
+    _sendRcpt(recipient, callback) {
+        this._recipientQueue.push(recipient);
+        this._responseActions.push(str => {
+            this._actionRCPT(str, callback);
+        });
+        this._sendCommand('RCPT TO:<' + recipient + '>' + this._getDsnRcptToArgs());
     }
     /** @internal */
     _setDsnEnvelope(params) {
@@ -1271,7 +1420,7 @@ class SMTPConnection extends EventEmitter {
      * @internal
      */
     _actionGreeting(str) {
-        clearTimeout(this._greetingTimeout);
+        this._clearPhase();
         if (str.substr(0, 3) !== '220') {
             this._onError(new Error('Invalid greeting. response=' + str), 'EPROTOCOL', str, 'CONN');
             return;
@@ -1309,7 +1458,6 @@ class SMTPConnection extends EventEmitter {
      * @internal
      */
     _actionEHLO(str) {
-        let match;
         if (str.substr(0, 3) === '421') {
             this._onError(new Error('Server terminates connection. response=' + str), 'ECONNECTION', str, 'EHLO');
             return;
@@ -1324,17 +1472,30 @@ class SMTPConnection extends EventEmitter {
             this._sendCommand('HELO ' + this.name);
             return;
         }
+        // Detect if the server supports STARTTLS
+        if (!this.secure && !this.options.ignoreTLS && (/[ -]STARTTLS\b/im.test(str) || this.options.requireTLS)) {
+            // kept for opportunisticTLS, a session that stays in plaintext still has these extensions
+            this._plaintextEhlo = str;
+            this._sendCommand('STARTTLS');
+            this._responseActions.push(this._actionSTARTTLS);
+            return;
+        }
+        this._parseEhloExtensions(str);
+        this.emit('connect');
+    }
+    /**
+     * Reads the extensions and the authentication mechanisms out of an EHLO response
+     *
+     * @param str EHLO response from the server
+     * @internal
+     */
+    _parseEhloExtensions(str) {
+        let match;
         this._ehloLines = str
             .split(/\r?\n/)
             .map(line => line.replace(/^\d+[ -]/, '').trim())
             .filter(line => line)
             .slice(1);
-        // Detect if the server supports STARTTLS
-        if (!this.secure && !this.options.ignoreTLS && (/[ -]STARTTLS\b/im.test(str) || this.options.requireTLS)) {
-            this._sendCommand('STARTTLS');
-            this._responseActions.push(this._actionSTARTTLS);
-            return;
-        }
         // Detect if the server supports SMTPUTF8
         if (/[ -]SMTPUTF8\b/im.test(str)) {
             this._supportedExtensions.push('SMTPUTF8');
@@ -1384,7 +1545,6 @@ class SMTPConnection extends EventEmitter {
             this._supportedExtensions.push('SIZE');
             this._maxAllowedSize = Number(match[1]) || 0;
         }
-        this.emit('connect');
     }
     /**
      * Handles server response for HELO command. If it yielded in
@@ -1416,6 +1576,14 @@ class SMTPConnection extends EventEmitter {
                 this.logger.info({
                     tnx: 'smtp'
                 }, 'Failed STARTTLS upgrade, continuing unencrypted');
+                // the plaintext session goes on with what the server announced for it, except for
+                // AUTH: credentials are not sent over a connection that failed to encrypt
+                if (this._plaintextEhlo) {
+                    this._parseEhloExtensions(this._plaintextEhlo);
+                    this._plaintextEhlo = false;
+                    this.allowsAuth = false;
+                    this._supportedAuth = [];
+                }
                 this.emit('connect');
                 return;
             }
@@ -1596,21 +1764,9 @@ class SMTPConnection extends EventEmitter {
             const message = this._usingSmtpUtf8 && /^550 /.test(str) && /[\x80-\uFFFF]/.test(envelope.from)
                 ? 'Internationalized mailbox name not allowed'
                 : 'Mail command failed';
-            return callback(this._formatError(message, 'EENVELOPE', str, 'MAIL FROM'));
+            envelope.mailError = this._formatError(message, 'EENVELOPE', str, 'MAIL FROM');
         }
-        if (!envelope.rcptQueue.length) {
+        this._advanceEnvelope(str, callback);
-            return callback(this._formatError("Can't send mail - no recipients defined", 'EENVELOPE', false, 'API'));
-        }
-        this._recipientQueue = [];
-        const usePipelining = this._supportedExtensions.includes('PIPELINING');
-        do {
-            const curRecipient = envelope.rcptQueue.shift();
-            this._recipientQueue.push(curRecipient);
-            this._responseActions.push(str => {
-                this._actionRCPT(str, callback);
-            });
-            this._sendCommand('RCPT TO:<' + curRecipient + '>' + this._getDsnRcptToArgs());
-        } while (usePipelining && envelope.rcptQueue.length);
     }
     /**
      * Handle response for a RCPT TO: command
@@ -1637,32 +1793,67 @@ class SMTPConnection extends EventEmitter {
         else {
             envelope.accepted.push(curRecipient);
         }
-        if (!envelope.rcptQueue.length && !this._recipientQueue.length) {
+        this._advanceEnvelope(str, callback);
-            if (envelope.rejected.length < envelope.to.length) {
+    }
+    /**
+     * Moves the envelope on after a reply to MAIL FROM or RCPT TO. A pipelined envelope sent every
+     * command at once and is decided by the reply to DATA. Otherwise the commands go one at a
+     * time: the next recipient, or once every reply is in, DATA or the error that ends the message
+     *
+     * @param str The reply that was handled
+     * @param callback Callback to run once the envelope is processed
+     * @internal
+     */
+    _advanceEnvelope(str, callback) {
+        const envelope = this._envelope;
+        if (envelope.pipelined) {
+            return;
+        }
+        if (envelope.mailError) {
+            return callback(envelope.mailError);
+        }
+        if (envelope.rcptQueue.length) {
+            return this._sendRcpt(envelope.rcptQueue.shift(), callback);
+        }
+        if (this._recipientQueue.length) {
+            // replies still to come
+            return;
+        }
+        const err = this._envelopeError(str);
+        if (err) {
+            return callback(err);
+        }
         this._responseActions.push(str => {
             this._actionDATA(str, callback);
         });
         this._sendCommand('DATA');
     }
-            else {
+    /**
+     * Decides how the envelope went once every reply to MAIL FROM and RCPT TO is in. Called after
+     * the last RCPT TO reply, or with PIPELINING on the reply to the DATA command sent along
+     *
+     * @param str The reply being handled
+     * @returns The error to fail the message with, or null when DATA can go ahead
+     * @internal
+     */
+    _envelopeError(str) {
+        const envelope = this._envelope;
+        if (envelope.mailError) {
+            return envelope.mailError;
+        }
+        if (envelope.accepted.length) {
+            return null;
+        }
         // report a temporary rejection when there is one, taking the last reply would mark the
         // whole message as permanently failed although some recipients were only deferred
         const deferred = envelope.rejectedErrors.find(rejectedErr => rejectedErr.responseCode && rejectedErr.responseCode < 500);
-                const reply = deferred?.response ?? str;
+        const lastRejected = envelope.rejectedErrors[envelope.rejectedErrors.length - 1];
-                err = this._formatError("Can't send mail - all recipients were rejected", 'EENVELOPE', reply, 'RCPT TO');
+        const reply = deferred?.response ?? (envelope.pipelined && lastRejected ? lastRejected.response : str);
+        // every recipient was rejected
+        const err = this._formatError("Can't send mail - all recipients were rejected", 'EENVELOPE', reply, 'RCPT TO');
         err.rejected = envelope.rejected;
         err.rejectedErrors = envelope.rejectedErrors;
-                return callback(err);
+        return err;
-            }
-        }
-        else if (envelope.rcptQueue.length) {
-            const nextRecipient = envelope.rcptQueue.shift();
-            this._recipientQueue.push(nextRecipient);
-            this._responseActions.push(str => {
-                this._actionRCPT(str, callback);
-            });
-            this._sendCommand('RCPT TO:<' + nextRecipient + '>' + this._getDsnRcptToArgs());
-        }
     }
     /**
      * Handle response for a DATA command
@@ -1673,6 +1864,27 @@ class SMTPConnection extends EventEmitter {
      */
     _actionDATA(str, callback) {
         const envelope = this._envelope;
+        if (envelope.pipelined) {
+            const err = this._envelopeError(str);
+            if (err) {
+                if (/^3/.test(str)) {
+                    if (envelope.mailError) {
+                        // A server that refused the sender has no transaction to end, one that
+                        // took DATA anyway can not be trusted with an empty message either.
+                        // Drop the connection instead of answering it
+                        this.close();
+                        return callback(err);
+                    }
+                    // A server must refuse DATA without an accepted recipient, this one took it
+                    // anyway. End the empty message, it has nobody to go to, so the session
+                    // stays usable
+                    this._responseActions.push(() => callback(err));
+                    this._sendCommand('.');
+                    return;
+                }
+                return callback(err);
+            }
+        }
         // response should be 354 but according to this issue https://github.com/eleith/emailjs/issues/24
         // some servers might use 250 instead, so lets check for 2 or 3 as the first digit
         if (!/^[23]/.test(str)) {

node_modules/nodemailer/dist/esm/smtp-pool/index.d.ts

@@ -19,6 +19,8 @@ export interface SMTPPoolOptions extends SMTPTransportOptions {
     rateDelta?: number | undefined;
     /** How many times a message is requeued when its connection closes while sending, defaults to 5, a negative value means unlimited */
     maxRequeues?: number | undefined;
+    /** Time in milliseconds a connection may stay idle before it is closed, defaults to 4 minutes, 0 keeps it open until the server closes it */
+    idleTimeout?: number | undefined;
 }
 /**
  * The pool options once the constructor has applied the defaults
@@ -27,6 +29,7 @@ export type SMTPPoolResolvedOptions = SMTPPoolOptions & {
     maxConnections: number;
     maxMessages: number;
     maxRequeues: number;
+    idleTimeout: number;
 };
 /**
  * Result of a message sent through the pool, same as for the SMTP transport

node_modules/nodemailer/dist/esm/smtp-pool/index.js

@@ -42,6 +42,9 @@ class SMTPPool extends EventEmitter {
         this.options.maxMessages = this.options.maxMessages || 100;
         // a default bound, a server that closes every connection before the greeting would otherwise be retried forever
         this.options.maxRequeues = typeof this.options.maxRequeues === 'number' ? this.options.maxRequeues : 5;
+        // below the 5 minutes RFC 5321 asks servers to wait at least, the connection is closed by us
+        // and not by the server in the middle of handing it a message
+        this.options.idleTimeout = typeof this.options.idleTimeout === 'number' ? this.options.idleTimeout : 4 * 60 * 1000;
         this.logger = shared.getLogger(this.options, {
             component: this.options.component || 'smtp-pool'
         });
@@ -448,7 +451,9 @@ class SMTPPool extends EventEmitter {
         // the error paths hand over the error alone
         const done = callback;
         const auth = new PoolResource(this).auth;
-        this.getSocket(this.options, (err, socketOptions) => {
+        // the proxy handshake, if any, counts against connectionTimeout as well
+        const connectStartedAt = Date.now();
+        this.getSocket(Object.assign({}, this.options, { connectStartedAt }), (err, socketOptions) => {
             if (err) {
                 return done(err);
             }
@@ -465,6 +470,7 @@ class SMTPPool extends EventEmitter {
                 options = Object.assign(shared.assign(false, options), socketOptions);
             }
             const connection = new SMTPConnection(options);
+            connection._connectStartedAt = connectStartedAt;
             let returned = false;
             connection.once('error', err => {
                 if (returned) {

node_modules/nodemailer/dist/esm/smtp-pool/pool-resource.js

@@ -52,6 +52,8 @@ export default class PoolResource extends EventEmitter {
         this.messages = 0;
         this.available = true;
         this._failed = false;
+        this._sending = false;
+        this._idleTimer = false;
     }
     /**
      * Emits 'error' for the first failure only. A dead resource can report the same failure more
@@ -71,7 +73,9 @@ export default class PoolResource extends EventEmitter {
      * @param callback Callback function to run once the connection is established or failed
      */
     connect(callback) {
-        this.pool.getSocket(this.options, (err, socketOptions) => {
+        // the proxy handshake, if any, counts against connectionTimeout as well
+        const connectStartedAt = Date.now();
+        this.pool.getSocket(Object.assign({}, this.options, { connectStartedAt }), (err, socketOptions) => {
             if (err) {
                 // nothing was connected, so no 'close' event is coming that would free the
                 // slot this resource holds in the pool, report the failure the way a failed
@@ -93,7 +97,21 @@ export default class PoolResource extends EventEmitter {
                 options = Object.assign(assign(false, options), socketOptions);
             }
             this.connection = new SMTPConnection(options);
-            this.connection.on('error', err => {
+            this.connection._connectStartedAt = connectStartedAt;
+            this.connection.on('error', (err) => {
+                if (this._sending) {
+                    // the send callback gets the same error and decides what it means for the message
+                    return;
+                }
+                if (this._connected && errors.isTransientError(err)) {
+                    // the server ended a connection that had nothing in flight, usually after it
+                    // was idle for a while. The 'end' that follows closes this resource
+                    this.logger.info({
+                        tnx: 'pool',
+                        cid: this.id
+                    }, 'Connection #%s was closed by the server: %s', this.id, err.message);
+                    return;
+                }
                 this._fail(err);
                 if (returned) {
                     return;
@@ -171,9 +189,39 @@ export default class PoolResource extends EventEmitter {
         if (mail.data.requireTLSExtensionEnabled) {
             envelope.requireTLSExtensionEnabled = mail.data.requireTLSExtensionEnabled;
         }
-        this.connection.send(envelope, mail.message.createReadStream(), (err, info) => {
+        this._sending = true;
+        // a connection that sent messages before may have been dropped by the server in between
+        const reused = this.messages > 0;
+        const messageStream = mail.message.createReadStream();
+        this.connection.send(envelope, messageStream, (err, info) => {
+            this._sending = false;
             this.messages++;
             if (err) {
+                if (reused && messageStream.readableDidRead === false && errors.isTransientError(err)) {
+                    // Not a byte of the message was sent, so it can go out over another
+                    // connection. The pool requeues the message when this resource closes
+                    this.logger.info({
+                        tnx: 'pool',
+                        cid: this.id,
+                        messageId
+                    }, 'Connection #%s was closed by the server before message %s was sent: %s', this.id, messageId, err.message);
+                    this.connection.close();
+                    return;
+                }
+                if ((err.code === errors.EENVELOPE || err.code === errors.EMESSAGE) &&
+                    err.responseCode !== 421 &&
+                    !this.connection._destroyed) {
+                    // The server refused this message, the connection itself is fine. Reset the
+                    // session and keep using it instead of opening a new one
+                    this.connection.reset(resetErr => {
+                        if (resetErr) {
+                            this.connection.close();
+                            return;
+                        }
+                        this._release();
+                    });
+                    return callback(err);
+                }
                 this.connection.close();
                 this._fail(err);
                 return callback(err);
@@ -183,28 +231,69 @@ export default class PoolResource extends EventEmitter {
                 to: envelope.to
             };
             info.messageId = messageId;
-            setImmediate(() => {
+            setImmediate(() => this._release());
+            callback(null, info);
+        });
+    }
+    /**
+     * Makes the connection available for the next message, or closes it once it has sent
+     * maxMessages messages
+     *
+     * @internal
+     */
+    _release() {
         if (this.messages >= this.options.maxMessages) {
             const err = new Error('Resource exhausted');
             err.code = errors.EMAXLIMIT;
             this.connection.close();
             this._fail(err);
+            return;
         }
-                else {
         this.pool._checkRateLimit(() => {
             this.available = true;
+            this._startIdleTimer();
             this.emit('available');
         });
     }
-            });
+    /** @internal */
-            callback(null, info);
+    _startIdleTimer() {
-        });
+        if (!this.options.idleTimeout || this.options.idleTimeout < 0) {
+            return;
+        }
+        // one timer per connection, restarted every time the connection becomes available. A
+        // connection that is busy when it fires is simply not closed
+        if (this._idleTimer && typeof this._idleTimer.refresh === 'function') {
+            this._idleTimer.refresh();
+            return;
+        }
+        clearTimeout(this._idleTimer);
+        this._idleTimer = setTimeout(() => {
+            if (!this.available) {
+                return;
+            }
+            this.logger.debug({
+                tnx: 'pool',
+                cid: this.id
+            }, 'Closing connection #%s after it was idle for %sms', this.id, this.options.idleTimeout);
+            // not handed another message while it says goodbye
+            this.available = false;
+            this.connection.quit();
+        }, this.options.idleTimeout);
+        if (typeof this._idleTimer.unref === 'function') {
+            this._idleTimer.unref();
+        }
+    }
+    /** @internal */
+    _stopIdleTimer() {
+        clearTimeout(this._idleTimer);
+        this._idleTimer = false;
     }
     /**
      * Closes the connection
      */
     close() {
         this._connected = false;
+        this._stopIdleTimer();
         if (this.auth && this.auth.oauth2) {
             this.auth.oauth2.removeAllListeners();
         }

node_modules/nodemailer/dist/esm/smtp-transport/index.js

@@ -104,7 +104,9 @@ class SMTPTransport extends EventEmitter {
      * @param callback Callback function
      */
     send(mail, callback) {
-        this.getSocket(this.options, (err, socketOptions) => {
+        // the proxy handshake, if any, counts against connectionTimeout as well
+        const connectStartedAt = Date.now();
+        this.getSocket(Object.assign({}, this.options, { connectStartedAt }), (err, socketOptions) => {
             if (err) {
                 return callback(err);
             }
@@ -123,6 +125,7 @@ class SMTPTransport extends EventEmitter {
                 options = Object.assign(shared.assign(false, options), socketOptions);
             }
             const connection = new SMTPConnection(options);
+            connection._connectStartedAt = connectStartedAt;
             let perCallAuth;
             const cleanupPerCallAuth = () => {
                 if (perCallAuth && perCallAuth !== this.auth && perCallAuth.oauth2) {
@@ -228,7 +231,9 @@ class SMTPTransport extends EventEmitter {
         }
         // the error paths hand over the error alone
         const done = callback;
-        this.getSocket(this.options, (err, socketOptions) => {
+        // the proxy handshake, if any, counts against connectionTimeout as well
+        const connectStartedAt = Date.now();
+        this.getSocket(Object.assign({}, this.options, { connectStartedAt }), (err, socketOptions) => {
             if (err) {
                 return done(err);
             }
@@ -245,6 +250,7 @@ class SMTPTransport extends EventEmitter {
                 options = Object.assign(shared.assign(false, options), socketOptions);
             }
             const connection = new SMTPConnection(options);
+            connection._connectStartedAt = connectStartedAt;
             let returned = false;
             let perCallAuth;
             const cleanupPerCallAuth = () => {

node_modules/nodemailer/package.json

@@ -1,6 +1,6 @@
 {
     "name": "nodemailer",
-    "version": "10.0.15",
+    "version": "10.1.0",
     "description": "Easy as cake e-mail sending from your Node.js applications",
     "type": "module",
     "main": "./dist/cjs/nodemailer.js",
@@ -168,7 +168,7 @@
         "smtp-server": "3.19.17",
         "tsx": "4.23.15",
         "typescript": "6.0.3",
-        "typescript-eslint": "8.71.0"
+        "typescript-eslint": "8.71.1"
     },
     "engines": {
         "node": ">=20.0.0"