node_modules: update (#338)

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

node_modules/.package-lock.json

@@ -94,9 +94,9 @@
       }
     },
     "node_modules/nodemailer": {
-      "version": "10.0.11",
+      "version": "10.0.13",
-      "resolved": "https://registry.npmjs.org/nodemailer/-/nodemailer-10.0.11.tgz",
+      "resolved": "https://registry.npmjs.org/nodemailer/-/nodemailer-10.0.13.tgz",
-      "integrity": "sha512-/c4P7U7aGpiNu2Rl08q525q2zECkUpSaf2zQPgIStCcAjHAkkQQKwD4sTyi3l91mGcLQrKzL1syXPHymo+Ogtw==",
+      "integrity": "sha512-SzG86OlvcW/NNhUFC6uROMwRTL4n7MswfQqC/T8mhkmnY1YVa23zUEMYi4ijSeXSl9GLz9ZeTJDUatEDuY5FeQ==",
       "license": "MIT-0",
       "engines": {
         "node": ">=20.0.0"

node_modules/nodemailer/CHANGELOG.md

@@ -1,5 +1,20 @@
 # CHANGELOG
 
+## [10.0.13](https://github.com/nodemailer/nodemailer/compare/v10.0.12...v10.0.13) (2026-09-30)
+
+
+### Bug Fixes
+
+* read the advertised SASL methods without backtracking regexes ([b5a896f](https://github.com/nodemailer/nodemailer/commit/b5a896fcb02df1628329d7cd665ca08490b14b56))
+* strip comments inside an angle-addr before it becomes the address ([a502247](https://github.com/nodemailer/nodemailer/commit/a502247555fd81773eac337486781f3b6008e16a))
+
+## [10.0.12](https://github.com/nodemailer/nodemailer/compare/v10.0.11...v10.0.12) (2026-09-28)
+
+
+### Bug Fixes
+
+* settle every send on a connection error, back off pool requeues, turn a bare CR into CRLF, bound fetch, honour requireTLS ([63ccd66](https://github.com/nodemailer/nodemailer/commit/63ccd66c894bbaac18c82084ee385bf6488226cf))
+
 ## [10.0.11](https://github.com/nodemailer/nodemailer/compare/v10.0.10...v10.0.11) (2026-09-27)
 
 

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

@@ -242,6 +242,81 @@ function _recoverAddrSpec(data) {
         .filter(part => part)
         .join(' ');
 }
+/**
+ * Takes the RFC 5322 comments out of the contents of an angle-addr.
+ *
+ * The tokenizer tracks a single open operator, so once '<' is open a '(' is plain text and
+ * a comment inside the brackets reached the address verbatim: 'Name <user@example.com(x)evil.com>'
+ * put 'user@example.com(x)evil.com' into the envelope, a value that is no mailbox and that a
+ * receiver stripping the comment reads as 'user@example.comevil.com' (GHSA-g73g-hqqh-jr95).
+ * A comment is folding whitespace, so it is read as a space that splits two atoms and as
+ * nothing next to an '@', the same rule the token walk applies outside the brackets. Quoted
+ * strings and domain literals are copied through untouched, a '(' in there is not a comment.
+ *
+ * @param address Contents of the angle brackets
+ * @return The address with the comments removed, and the text of the comments
+ */
+function _stripAddressComments(address) {
+    const comments = [];
+    let result = '';
+    let comment = '';
+    let depth = 0;
+    let closer = '';
+    // carried along rather than read back off the growing result, which would flatten it on
+    // every comment (see lastChars in _handleAddress)
+    let lastChar = '';
+    for (let i = 0, len = address.length; i < len; i++) {
+        const chr = address.charAt(i);
+        if (depth) {
+            if (chr === '\\' && i < len - 1) {
+                comment += address.charAt(++i);
+            }
+            else if (chr === '(') {
+                depth++;
+                comment += chr;
+            }
+            else if (chr === ')' && !--depth) {
+                comments.push(comment.trim());
+                comment = '';
+                if (lastChar !== '@' && address.charAt(i + 1) !== '@') {
+                    result += ' ';
+                    lastChar = ' ';
+                }
+            }
+            else {
+                comment += chr;
+            }
+            continue;
+        }
+        if (closer) {
+            if (chr === '\\' && closer === '"' && i < len - 1) {
+                result += chr + address.charAt(++i);
+                lastChar = address.charAt(i);
+                continue;
+            }
+            if (chr === closer) {
+                closer = '';
+            }
+        }
+        else if (chr === '"') {
+            closer = '"';
+        }
+        else if (chr === '[') {
+            closer = ']';
+        }
+        else if (chr === '(') {
+            depth = 1;
+            continue;
+        }
+        result += chr;
+        lastChar = chr;
+    }
+    if (depth) {
+        // an unterminated comment runs to the end of the address
+        comments.push(comment.trim());
+    }
+    return { address: result.trim(), comments: comments.filter(text => text) };
+}
 /**
  * Converts tokens for a single address into an address object
  *
@@ -369,6 +444,24 @@ function _handleAddress(tokens, depth) {
         });
     }
     else {
+        // Comments come out of the angle-addr before anything asks whether one was found, so
+        // that brackets holding nothing but a comment read the same as empty ones
+        const addressComments = [];
+        const addressParts = [];
+        for (const part of data.address) {
+            if (part.indexOf('(') < 0) {
+                addressParts.push(part);
+                continue;
+            }
+            const stripped = _stripAddressComments(part);
+            for (const comment of stripped.comments) {
+                addressComments.push(comment);
+            }
+            if (stripped.address) {
+                addressParts.push(stripped.address);
+            }
+        }
+        data.address = addressParts;
         // If no address was found, try to detect one from regular text
         if (!data.address.length && data.text.length) {
             for (let i = data.text.length - 1; i >= 0; i--) {
@@ -435,6 +528,10 @@ function _handleAddress(tokens, depth) {
             data.text = '';
         }
         _recoverAddrSpec(data);
+        // a comment names the mailbox only when nothing else does, as one outside the brackets
+        if (!data.text && addressComments.length) {
+            data.text = addressComments.join(' ');
+        }
         const address = {
             address: data.address || data.text || '',
             name: data.text || data.address || ''

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

@@ -90,13 +90,22 @@ class DKIMSigner {
                 return;
             }
             const key = this.keys[keyPos++];
-            const dkimField = (0, sign_js_1.default)(this.headers, this.hashAlgo, this.bodyHash, {
+            let dkimField;
-                domainName: key.domainName,
+            try {
-                keySelector: key.keySelector,
+                dkimField = (0, sign_js_1.default)(this.headers, this.hashAlgo, this.bodyHash, {
-                privateKey: key.privateKey,
+                    domainName: key.domainName,
-                headerFieldNames: this.options.headerFieldNames,
+                    keySelector: key.keySelector,
-                skipFields: this.options.skipFields
+                    privateKey: key.privateKey,
-            });
+                    headerFieldNames: this.options.headerFieldNames,
+                    skipFields: this.options.skipFields
+                });
+            }
+            catch (err) {
+                this.hasErrored = true;
+                this.cleanup();
+                this.output.emit('error', err);
+                return;
+            }
             if (dkimField) {
                 this.output.write(Buffer.from(dkimField + '\r\n'));
             }
@@ -196,7 +205,15 @@ class DKIM {
         }
         const signer = new DKIMSigner(options, this.keys, inputStream, output);
         setImmediate(() => {
-            signer.signStream();
+            try {
+                signer.signStream();
+            }
+            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));
+                return;
+            }
             if (writeValue) {
                 setImmediate(() => {
                     inputStream.end(writeValue);

node_modules/nodemailer/dist/cjs/dkim/sign.d.ts

@@ -1,4 +1,5 @@
 import crypto from 'node:crypto';
+import type { NodemailerError } from '../errors.js';
 import type { MessageParserHeaderLine } from './message-parser.js';
 /**
  * Private key accepted by crypto.Sign#sign: a PEM string, a Buffer, a KeyObject or an
@@ -45,5 +46,6 @@ export interface DKIMRelaxedHeaders {
 declare function sign(headers: MessageParserHeaderLine[], hashAlgo: string, bodyHash: string, options?: DKIMSignOptions): string | false;
 declare namespace sign {
     var relaxedHeaders: (headers: MessageParserHeaderLine[], fieldNames?: string, skipFields?: string) => DKIMRelaxedHeaders;
+    var unsupportedHashAlgoError: (hashAlgo: string) => NodemailerError;
 }
 export default sign;

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

@@ -39,6 +39,15 @@ Object.defineProperty(exports, "__esModule", { value: true });
 const punycode = __importStar(require("../punycode/index.js"));
 const mimeFuncs = __importStar(require("../mime-funcs/index.js"));
 const node_crypto_1 = __importDefault(require("node:crypto"));
+const errors = __importStar(require("../errors.js"));
+/**
+ * Error for a hashAlgo value the crypto module does not know
+ */
+function unsupportedHashAlgoError(hashAlgo) {
+    const err = new Error('Unsupported DKIM hash algorithm "' + hashAlgo + '"');
+    err.code = errors.ECONFIG;
+    return err;
+}
 /**
  * Returns DKIM signature header line
  *
@@ -63,7 +72,13 @@ function sign(headers, hashAlgo, bodyHash, options) {
     const canonicalizedHeaderData = relaxedHeaders(headers, fieldNames, options.skipFields);
     const dkimHeader = generateDKIMHeader(options.domainName, options.keySelector, canonicalizedHeaderData.fieldNames, hashAlgo, bodyHash);
     canonicalizedHeaderData.headers += 'dkim-signature:' + relaxedHeaderLine(dkimHeader);
-    const signer = node_crypto_1.default.createSign(('rsa-' + hashAlgo).toUpperCase());
+    let signer;
+    try {
+        signer = node_crypto_1.default.createSign(('rsa-' + hashAlgo).toUpperCase());
+    }
+    catch (_E) {
+        throw unsupportedHashAlgoError(hashAlgo);
+    }
     // the header lines are 'binary' strings, so this reproduces the original header bytes
     signer.update(canonicalizedHeaderData.headers, 'latin1');
     let signature;
@@ -76,6 +91,7 @@ function sign(headers, hashAlgo, bodyHash, options) {
     return dkimHeader + signature.replace(/(^.{73}|.{75}(?!\r?\n|\r))/g, '$&\r\n ').trim();
 }
 sign.relaxedHeaders = relaxedHeaders;
+sign.unsupportedHashAlgoError = unsupportedHashAlgoError;
 exports.default = sign;
 function generateDKIMHeader(domainName, keySelector, fieldNames, hashAlgo, bodyHash) {
     // the caller supplied tag values are interpolated straight into the tag list, and none of

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

@@ -25,8 +25,10 @@ export interface FetchOptions {
     tls?: {
         [key: string]: any;
     } | undefined;
-    /** Request timeout in milliseconds */
+    /** Socket inactivity timeout in milliseconds, defaults to 60000, 0 disables it */
     timeout?: number | undefined;
+    /** Maximum size of the (decoded) response body in bytes, defaults to 64 MB, Infinity disables the limit */
+    maxBytes?: number | undefined;
     /** Maximum number of redirects to follow (default 5) */
     maxRedirects?: number | undefined;
     /** Resolve responses with a status code of 300 or above instead of emitting an error */
@@ -47,6 +49,7 @@ export interface FetchResponse extends PassThrough {
 declare function nmfetch(url: string, options?: FetchOptions): FetchResponse;
 declare namespace nmfetch {
     var Cookies: typeof import("./cookies.js").default;
+    var DEFAULT_TIMEOUT: number;
 }
 type CookiesJar = Cookies;
 /**

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

@@ -47,6 +47,10 @@ const node_net_1 = __importDefault(require("node:net"));
 const errors = __importStar(require("../errors.js"));
 const objects_js_1 = require("../shared/objects.js");
 const MAX_REDIRECTS = 5;
+// a stalled server would otherwise hold the request, and whatever waits on it, open forever
+const DEFAULT_TIMEOUT = 60 * 1000;
+// the body is usually buffered in memory by the caller, so an unbounded download is refused
+const DEFAULT_MAX_BYTES = 64 * 1024 * 1024;
 // Only genuine TLS settings are taken from options.tls. That object reaches us straight
 // from a user supplied attachment (content.tls), so keys like host, port, path, socketPath
 // or lookup would otherwise repoint the request at a destination that never went through
@@ -252,28 +256,22 @@ function nmfetch(url, options) {
         });
         return fetchRes;
     }
-    if (options.timeout) {
+    // reports the first failure of this request on fetchRes and releases the request
-        req.setTimeout(options.timeout, () => {
+    const fail = (err, sourceUrl = url) => {
-            if (finished) {
-                return;
-            }
-            finished = true;
-            req.abort();
-            const err = new Error('Request Timeout');
-            err.code = errors.EFETCH;
-            err.sourceUrl = url;
-            fetchRes.emit('error', err);
-        });
-    }
-    req.on('error', (err) => {
         if (finished) {
             return;
         }
         finished = true;
         err.code = errors.EFETCH;
-        err.sourceUrl = url;
+        err.sourceUrl = sourceUrl;
         fetchRes.emit('error', err);
-    });
+        req.abort();
+    };
+    const timeout = typeof options.timeout === 'number' && options.timeout >= 0 ? options.timeout : DEFAULT_TIMEOUT;
+    if (timeout) {
+        req.setTimeout(timeout, () => fail(new Error('Request Timeout')));
+    }
+    req.on('error', (err) => fail(err));
     req.on('response', res => {
         let inflate;
         if (finished) {
@@ -294,13 +292,7 @@ function nmfetch(url, options) {
             // redirect
             options.redirects++;
             if (options.redirects > options.maxRedirects) {
-                finished = true;
+                return fail(new Error('Maximum redirect count exceeded'));
-                const err = new Error('Maximum redirect count exceeded');
-                err.code = errors.EFETCH;
-                err.sourceUrl = url;
-                fetchRes.emit('error', err);
-                req.abort();
-                return;
             }
             // redirect does not include POST body
             options.method = 'GET';
@@ -320,13 +312,7 @@ function nmfetch(url, options) {
                 // call: that call gets its own `finished` flag and no handle on this
                 // request, so this one would stay open and could emit a second error on
                 // the shared fetchRes once it times out. Callers listen with req.once().
-                finished = true;
+                return fail(new Error('Unsupported protocol for URL ' + redirectUrl), redirectUrl);
-                const err = new Error('Unsupported protocol for URL ' + redirectUrl);
-                err.code = errors.EFETCH;
-                err.sourceUrl = redirectUrl;
-                fetchRes.emit('error', err);
-                req.abort();
-                return;
             }
             // Do not forward credentials when the redirect leaves the original
             // security context: a different host, or a downgrade from https to
@@ -343,41 +329,33 @@ function nmfetch(url, options) {
                     }
                 });
             }
+            // this request is done with, release it so its socket and timeout do not
+            // outlive it and report a late error on the shared fetchRes
+            finished = true;
+            res.resume();
+            req.abort();
             return nmfetch(redirectUrl, options);
         }
         fetchRes.statusCode = res.statusCode;
         fetchRes.headers = res.headers;
         if (res.statusCode >= 300 && !options.allowErrorResponse) {
-            finished = true;
+            return fail(new Error('Invalid status code ' + res.statusCode));
-            const err = new Error('Invalid status code ' + res.statusCode);
-            err.code = errors.EFETCH;
-            err.sourceUrl = url;
-            fetchRes.emit('error', err);
-            req.abort();
-            return;
         }
-        res.on('error', (err) => {
+        res.on('error', (err) => fail(err));
-            if (finished) {
+        const maxBytes = typeof options.maxBytes === 'number' && options.maxBytes > 0 ? options.maxBytes : DEFAULT_MAX_BYTES;
+        const source = inflate || res;
+        let received = 0;
+        source.on('data', (chunk) => {
+            received += chunk.length;
+            if (received <= maxBytes || finished) {
                 return;
             }
-            finished = true;
+            source.unpipe(fetchRes);
-            err.code = errors.EFETCH;
+            fail(new Error('Response size exceeds the allowed ' + maxBytes + ' bytes'));
-            err.sourceUrl = url;
-            fetchRes.emit('error', err);
-            req.abort();
         });
         if (inflate) {
             res.pipe(inflate).pipe(fetchRes);
-            inflate.on('error', (err) => {
+            inflate.on('error', (err) => fail(err));
-                if (finished) {
-                    return;
-                }
-                finished = true;
-                err.code = errors.EFETCH;
-                err.sourceUrl = url;
-                fetchRes.emit('error', err);
-                req.abort();
-            });
         }
         else {
             res.pipe(fetchRes);
@@ -392,11 +370,7 @@ function nmfetch(url, options) {
                 req.write(body);
             }
             catch (err) {
-                finished = true;
+                return fail(err);
-                err.code = errors.EFETCH;
-                err.sourceUrl = url;
-                fetchRes.emit('error', err);
-                return;
             }
         }
         req.end();
@@ -404,6 +378,7 @@ function nmfetch(url, options) {
     return fetchRes;
 }
 nmfetch.Cookies = cookies_js_1.default;
+nmfetch.DEFAULT_TIMEOUT = DEFAULT_TIMEOUT;
 exports.default = nmfetch;
 module.exports = exports.default;
 Object.defineProperty(module.exports, 'default', { value: exports.default, enumerable: false, writable: true, configurable: true });

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

@@ -1,3 +1,3 @@
 export declare const name = "nodemailer";
-export declare const version = "10.0.11";
+export declare const version = "10.0.13";
 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 = '10.0.11';
+exports.version = '10.0.13';
 exports.homepage = 'https://nodemailer.com/';

node_modules/nodemailer/dist/cjs/smtp-connection/data-stream.d.ts

@@ -1,7 +1,8 @@
 import { Transform, type TransformOptions } from 'node:stream';
 /**
  * Escapes dots in the beginning of lines. Ends the stream with <CR><LF>.<CR><LF>
- * Also makes sure that only <CR><LF> sequences are used for linebreaks
+ * Also makes sure that only <CR><LF> sequences are used for linebreaks, bare CR and bare LF
+ * are both turned into <CR><LF>
  *
  * @param options Stream options
  */

node_modules/nodemailer/dist/cjs/smtp-connection/data-stream.js

@@ -1,9 +1,15 @@
 "use strict";
 Object.defineProperty(exports, "__esModule", { value: true });
 const node_stream_1 = require("node:stream");
+// bytes inserted into the output, shared as they are only ever copied by Buffer.concat
+const INSERT_LF = Buffer.from('\n');
+const INSERT_LF_DOT = Buffer.from('\n.');
+const INSERT_CR = Buffer.from('\r');
+const INSERT_DOT = Buffer.from('.');
 /**
  * Escapes dots in the beginning of lines. Ends the stream with <CR><LF>.<CR><LF>
- * Also makes sure that only <CR><LF> sequences are used for linebreaks
+ * Also makes sure that only <CR><LF> sequences are used for linebreaks, bare CR and bare LF
+ * are both turned into <CR><LF>
  *
  * @param options Stream options
  */
@@ -32,33 +38,35 @@ class DataStream extends node_stream_1.Transform {
         }
         this.inByteCount += chunk.length;
         for (i = 0, len = chunk.length; i < len; i++) {
-            if (chunk[i] === 0x2e) {
+            const byte = chunk[i];
-                // .
+            const prev = i ? chunk[i - 1] : this.lastByte;
-                if ((i && chunk[i - 1] === 0x0a) || (!i && (!this.lastByte || this.lastByte === 0x0a))) {
+            let insert = false;
-                    buf = chunk.slice(lastPos, i + 1);
+            if (prev === 0x0d && byte !== 0x0a) {
-                    chunks.push(buf);
+                // a bare CR becomes CRLF. A receiver that treats a lone CR as a line end would
-                    chunks.push(Buffer.from('.'));
+                // otherwise see "\r.\r" as the end of the data (SMTP smuggling), so a dot
-                    chunklen += buf.length + 1;
+                // following it is stuffed like at the start of any other line
-                    lastPos = i + 1;
+                insert = byte === 0x2e ? INSERT_LF_DOT : INSERT_LF;
-                }
             }
-            else if (chunk[i] === 0x0a) {
+            else if (byte === 0x0a && prev !== 0x0d) {
-                // \n
+                // a bare LF becomes CRLF
-                if ((i && chunk[i - 1] !== 0x0d) || (!i && this.lastByte !== 0x0d)) {
+                insert = INSERT_CR;
-                    if (i > lastPos) {
+            }
-                        buf = chunk.slice(lastPos, i);
+            else if (byte === 0x2e && (prev === 0x0a || prev === false)) {
-                        chunks.push(buf);
+                // a dot at the start of a line
-                        chunklen += buf.length + 2;
+                insert = INSERT_DOT;
-                    }
+            }
-                    else {
+            if (insert) {
-                        chunklen += 2;
+                if (i > lastPos) {
-                    }
+                    buf = chunk.slice(lastPos, i);
-                    chunks.push(Buffer.from('\r\n'));
+                    chunks.push(buf);
-                    lastPos = i + 1;
+                    chunklen += buf.length;
                 }
+                chunks.push(insert);
+                chunklen += insert.length;
+                lastPos = i;
             }
         }
-        if (chunklen) {
+        if (chunks.length) {
             // add last piece
             if (lastPos < chunk.length) {
                 buf = chunk.slice(lastPos);

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

@@ -26,11 +26,11 @@ export interface SMTPConnectionOptions {
     secured?: boolean | undefined;
     /** Server name for SNI, defaults to host when that is not an IP address */
     servername?: string | undefined;
-    /** Ignore STARTTLS even when the server advertises it */
+    /** Ignore STARTTLS even when the server advertises it, has no effect when requireTLS is set */
     ignoreTLS?: boolean | undefined;
-    /** Force STARTTLS, fail when the server does not support it */
+    /** Force STARTTLS, fail when the server does not support it. Takes precedence over ignoreTLS and opportunisticTLS */
     requireTLS?: boolean | undefined;
-    /** Continue unencrypted when the STARTTLS upgrade fails */
+    /** Continue unencrypted when the STARTTLS upgrade fails, has no effect when requireTLS is set */
     opportunisticTLS?: boolean | undefined;
     /** Name of the client server, sent with EHLO/HELO, CRLF is stripped */
     name?: string | undefined;
@@ -288,8 +288,8 @@ export type SMTPConnectionResponseAction = (str: string) => void;
  *  * **port** - is the port to connect to (defaults to 587 or 465)
  *  * **host** - is the hostname or IP address to connect to (defaults to 'localhost')
  *  * **secure** - use SSL
- *  * **ignoreTLS** - ignore server support for STARTTLS
+ *  * **ignoreTLS** - ignore server support for STARTTLS (has no effect when requireTLS is set)
- *  * **requireTLS** - forces the client to use STARTTLS
+ *  * **requireTLS** - forces the client to use STARTTLS, takes precedence over ignoreTLS and opportunisticTLS
  *  * **name** - the name of the client server
  *  * **localAddress** - outbound address to bind to (see: http://nodejs.org/api/net.html#net_net_connect_options_connectionlistener)
  *  * **greetingTimeout** - Time to wait in ms until greeting message is received from the server (defaults to 30 seconds)

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

@@ -104,8 +104,8 @@ function isPartialLine(line) {
  *  * **port** - is the port to connect to (defaults to 587 or 465)
  *  * **host** - is the hostname or IP address to connect to (defaults to 'localhost')
  *  * **secure** - use SSL
- *  * **ignoreTLS** - ignore server support for STARTTLS
+ *  * **ignoreTLS** - ignore server support for STARTTLS (has no effect when requireTLS is set)
- *  * **requireTLS** - forces the client to use STARTTLS
+ *  * **requireTLS** - forces the client to use STARTTLS, takes precedence over ignoreTLS and opportunisticTLS
  *  * **name** - the name of the client server
  *  * **localAddress** - outbound address to bind to (see: http://nodejs.org/api/net.html#net_net_connect_options_connectionlistener)
  *  * **greetingTimeout** - Time to wait in ms until greeting message is received from the server (defaults to 30 seconds)
@@ -130,6 +130,11 @@ class SMTPConnection extends node_events_1.EventEmitter {
         this.id = node_crypto_1.default.randomBytes(8).toString('base64').replace(/\W/g, '');
         this.stage = 'init';
         this.options = options || {};
+        if (this.options.requireTLS && (this.options.ignoreTLS || this.options.opportunisticTLS)) {
+            // requireTLS wins, a contradictory configuration must not quietly fall back to plaintext.
+            // Copied so the caller's (possibly shared) options object is left as it was
+            this.options = Object.assign({}, this.options, { ignoreTLS: false, opportunisticTLS: false });
+        }
         this.secureConnection = !!this.options.secure;
         this.alreadySecured = !!this.options.secured;
         this.port = Number(this.options.port) || (this.secureConnection ? 465 : 587);
@@ -173,6 +178,8 @@ class SMTPConnection extends node_events_1.EventEmitter {
         this._destroyed = false;
         this._closing = false;
         this._currentDataStream = false;
+        this._pendingSend = false;
+        this._connectCallback = false;
         this._onSocketData = chunk => this._onData(chunk);
         this._onSocketError = error => this._onError(error, 'ESOCKET', false, 'CONN');
         this._onSocketClose = () => this._onClose();
@@ -187,7 +194,9 @@ class SMTPConnection extends node_events_1.EventEmitter {
      */
     connect(connectCallback) {
         if (typeof connectCallback === 'function') {
+            this._connectCallback = connectCallback;
             this.once('connect', () => {
+                this._connectCallback = false;
                 this.logger.debug({
                     tnx: 'smtp'
                 }, 'SMTP handshake finished');
@@ -419,6 +428,16 @@ 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
+        // removed, a stream destroyed with an error later on 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);
+            }
+            this._pendingSend = false;
+        }
         if (socket && !socket.destroyed) {
             try {
                 // Clear socket timeout to prevent timer leaks
@@ -606,6 +625,9 @@ class SMTPConnection extends node_events_1.EventEmitter {
                 return;
             }
             returned = true;
+            if (this._pendingSend && this._pendingSend.callback === callback) {
+                this._pendingSend = false;
+            }
             done(err, info);
         };
         if (!message) {
@@ -622,9 +644,16 @@ class SMTPConnection extends node_events_1.EventEmitter {
             });
             return;
         }
+        const pendingSend = {
+            callback,
+            stream: false,
+            onStreamError: err => callback(this._formatError(err, 'ESTREAM', false, 'API'))
+        };
         if (typeof message.on === 'function') {
-            message.on('error', err => callback(this._formatError(err, 'ESTREAM', false, 'API')));
+            pendingSend.stream = message;
+            pendingSend.stream.on('error', pendingSend.onStreamError);
         }
+        this._pendingSend = pendingSend;
         const startTime = Date.now();
         this._setEnvelope(envelope, (err, info) => {
             if (err) {
@@ -817,8 +846,14 @@ class SMTPConnection extends node_events_1.EventEmitter {
         else {
             this.logger.error(data, 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
+        const pendingSend = this._pendingSend;
         this.emit('error', err);
         this.close();
+        if (pendingSend) {
+            pendingSend.callback(err);
+        }
     }
     /** @internal */
     _formatError(message, type, response, command) {
@@ -864,14 +899,25 @@ class SMTPConnection extends node_events_1.EventEmitter {
         this.logger.info({
             tnx: 'network'
         }, 'Connection closed');
+        // the unterminated remainder is only reported as a reply (and so gives the error a responseCode)
+        // when it starts like a complete failure reply, not for a fragment such as "55" or a 250
+        const failureResponse = typeof serverResponse === 'string' && /^[45]\d{2}[ -]/.test(serverResponse) ? serverResponse : false;
         if (this.upgrading && !this._destroyed) {
-            return this._onError(new Error('Connection closed unexpectedly'), 'ETLS', serverResponse, 'CONN');
+            return this._onError(new Error('Connection closed unexpectedly'), 'ETLS', failureResponse, 'CONN');
         }
-        else if (![this._actionGreeting, this.close].includes(this._responseActions[0]) && !this._destroyed) {
+        if (!failureResponse && this._responseActions[0] === this._actionGreeting && this._connectCallback && !this._destroyed) {
-            return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', serverResponse, 'CONN');
+            // A silent close before the greeting is handed to the connect() callback rather than
+            // emitted as 'error', callers that never saw an error for it must not start throwing one
+            const connectCallback = this._connectCallback;
+            this._connectCallback = false;
+            const err = this._formatError(new Error('Connection closed unexpectedly'), 'ECONNECTION', false, 'CONN');
+            this.logger.warn({ tnx: 'network' }, err.message);
+            connectCallback(err);
+            this.close();
+            return;
         }
-        else if (/^[45]\d{2}\b/.test(serverResponse)) {
+        if (failureResponse || (this._responseActions[0] !== this.close && !this._destroyed)) {
-            return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', serverResponse, 'CONN');
+            return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', failureResponse, 'CONN');
         }
         this._destroy();
     }
@@ -1348,21 +1394,25 @@ class SMTPConnection extends node_events_1.EventEmitter {
         if (/[ -]AUTH\b/i.test(str)) {
             this.allowsAuth = true;
         }
-        // Detect if the server supports PLAIN auth
+        // Detect the advertised SASL mechanisms. The list is split into whole tokens rather
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)PLAIN/i.test(str)) {
+        // than searched for each name with a pattern: the patterns this replaced let two
-            this._supportedAuth.push('PLAIN');
+        // whitespace runs overlap and backtracked quadratically over an AUTH line padded with
+        // spaces, so a hostile server could stall the event loop from its EHLO reply
+        // (GHSA-4ffr-jq9g-5ffx).
+        const authMechanisms = new Set();
+        for (const line of this._ehloLines) {
+            const authMatch = /^AUTH[\s=](.*)/i.exec(line);
+            if (authMatch) {
+                for (const mechanism of authMatch[1].split(/[\s=]+/)) {
+                    authMechanisms.add(mechanism.toUpperCase());
+                }
+            }
         }
-        // Detect if the server supports LOGIN auth
+        // listed in order of preference, the first one the credentials allow is used
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)LOGIN/i.test(str)) {
+        for (const mechanism of ['PLAIN', 'LOGIN', 'CRAM-MD5', 'XOAUTH2']) {
-            this._supportedAuth.push('LOGIN');
+            if (authMechanisms.has(mechanism)) {
-        }
+                this._supportedAuth.push(mechanism);
-        // Detect if the server supports CRAM-MD5 auth
+            }
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)CRAM-MD5/i.test(str)) {
-            this._supportedAuth.push('CRAM-MD5');
-        }
-        // Detect if the server supports XOAUTH2 auth
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)XOAUTH2/i.test(str)) {
-            this._supportedAuth.push('XOAUTH2');
         }
         // Detect if the server supports SIZE extensions (and the max allowed size)
         if ((match = str.match(/[ -]SIZE(?:[ \t]+(\d+))?/im))) {
@@ -1622,7 +1672,11 @@ class SMTPConnection extends node_events_1.EventEmitter {
                 this._sendCommand('DATA');
             }
             else {
-                err = this._formatError("Can't send mail - all recipients were rejected", 'EENVELOPE', str, 'RCPT TO');
+                // 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;
+                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);

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

@@ -17,7 +17,7 @@ export interface SMTPPoolOptions extends SMTPTransportOptions {
     rateLimit?: number | undefined;
     /** Time window for rateLimit in milliseconds, defaults to 1000 */
     rateDelta?: number | undefined;
-    /** How many times a message is requeued when its connection closes while sending, unlimited when not set or negative */
+    /** How many times a message is requeued when its connection closes while sending, defaults to 5, a negative value means unlimited */
     maxRequeues?: number | undefined;
 }
 /**
@@ -26,6 +26,7 @@ export interface SMTPPoolOptions extends SMTPTransportOptions {
 export type SMTPPoolResolvedOptions = SMTPPoolOptions & {
     maxConnections: number;
     maxMessages: number;
+    maxRequeues: number;
 };
 /**
  * Result of a message sent through the pool, same as for the SMTP transport

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

@@ -43,6 +43,10 @@ const index_js_2 = __importDefault(require("../well-known/index.js"));
 const shared = __importStar(require("../shared/index.js"));
 const errors = __importStar(require("../errors.js"));
 const packageData = __importStar(require("../package-info.js"));
+/** First delay before a requeued message is retried, doubled on every further requeue */
+const REQUEUE_BASE_DELAY = 50;
+/** Upper bound for the requeue delay */
+const REQUEUE_MAX_DELAY = 2000;
 /**
  * Creates a SMTP pool transport object for Nodemailer
  *
@@ -74,6 +78,8 @@ class SMTPPool extends node_events_1.EventEmitter {
         );
         this.options.maxConnections = this.options.maxConnections || 5;
         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;
         this.logger = shared.getLogger(this.options, {
             component: this.options.component || 'smtp-pool'
         });
@@ -117,6 +123,10 @@ class SMTPPool extends node_events_1.EventEmitter {
      */
     send(mail, callback) {
         if (this._closed) {
+            // Mail.sendMail ignores the return value, so without a callback its promise would never settle
+            const err = new Error('Connection pool was closed');
+            err.code = errors.ECONNECTION;
+            setImmediate(() => callback(err));
             return false;
         }
         this._queue.push({
@@ -330,15 +340,22 @@ class SMTPPool extends node_events_1.EventEmitter {
                 // Note that we must wait a bit.. because the callback of the 'error' handler might be called
                 // in the next event loop
                 setTimeout(() => {
+                    let delay = 0;
                     if (connection.queueEntry) {
                         if (this._shouldRequeuOnConnectionClose(connection.queueEntry)) {
-                            this._requeueEntryOnConnectionClose(connection);
+                            delay = this._requeueEntryOnConnectionClose(connection);
                         }
                         else {
                             this._failDeliveryOnConnectionClose(connection);
                         }
                     }
-                    this._continueProcessing();
+                    if (delay) {
+                        // back off, a server that keeps dropping connections is not hammered
+                        setTimeout(() => this._continueProcessing(), delay);
+                    }
+                    else {
+                        this._continueProcessing();
+                    }
                 }, 50);
             }
             else {
@@ -353,7 +370,7 @@ class SMTPPool extends node_events_1.EventEmitter {
     }
     /** @internal */
     _shouldRequeuOnConnectionClose(queueEntry) {
-        if (this.options.maxRequeues === undefined || this.options.maxRequeues < 0) {
+        if (this.options.maxRequeues < 0) {
             return true;
         }
         return queueEntry.requeueAttempts < this.options.maxRequeues;
@@ -362,7 +379,9 @@ class SMTPPool extends node_events_1.EventEmitter {
     _failDeliveryOnConnectionClose(connection) {
         if (connection.queueEntry && connection.queueEntry.callback) {
             try {
-                connection.queueEntry.callback(new Error('Reached maximum number of retries after connection was closed'));
+                const err = new Error('Reached maximum number of retries after connection was closed');
+                err.code = errors.ECONNECTION;
+                connection.queueEntry.callback(err);
             }
             catch (E) {
                 this.logger.error({
@@ -377,6 +396,7 @@ class SMTPPool extends node_events_1.EventEmitter {
     }
     /** @internal */
     _requeueEntryOnConnectionClose(connection) {
+        const delay = Math.min(REQUEUE_BASE_DELAY * 2 ** connection.queueEntry.requeueAttempts, REQUEUE_MAX_DELAY);
         connection.queueEntry.requeueAttempts += 1;
         this.logger.debug({
             tnx: 'pool',
@@ -386,6 +406,7 @@ class SMTPPool extends node_events_1.EventEmitter {
         }, 'Re-queued message <%s> for #%s. Attempt: #%s', connection.queueEntry.messageId, connection.id, connection.queueEntry.requeueAttempts);
         this._queue.unshift(connection.queueEntry);
         connection.queueEntry = false;
+        return delay;
     }
     /**
      * Continue to process message if the pool hasn't closed
@@ -506,10 +527,15 @@ class SMTPPool extends node_events_1.EventEmitter {
                 connection.quit();
                 return done(null, true);
             };
-            connection.connect(() => {
+            connection.connect(err => {
                 if (returned) {
                     return;
                 }
+                if (err) {
+                    returned = true;
+                    connection.close();
+                    return done(err);
+                }
                 if (auth && (connection.allowsAuth || options.forceAuth)) {
                     connection.login(auth, err => {
                         if (returned) {

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

@@ -66,7 +66,7 @@ class PoolResource extends node_events_1.EventEmitter {
                         method: 'XOAUTH2'
                     };
                     oauth2.on('token', (token) => this.pool.mailer.emit('token', token));
-                    oauth2.on('error', err => this.emit('error', err));
+                    oauth2.on('error', err => this._fail(err));
                     break;
                 }
                 default:
@@ -89,6 +89,19 @@ class PoolResource extends node_events_1.EventEmitter {
         this._connected = false;
         this.messages = 0;
         this.available = true;
+        this._failed = false;
+    }
+    /**
+     * Emits 'error' for the first failure only. A dead resource can report the same failure more
+     * than once (the connection error, then the send callback), the pool handles it once
+     * @internal
+     */
+    _fail(err) {
+        if (this._failed) {
+            return;
+        }
+        this._failed = true;
+        this.emit('error', err);
     }
     /**
      * Initiates a connection to the SMTP server
@@ -101,7 +114,7 @@ class PoolResource extends node_events_1.EventEmitter {
                 // 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
                 // login does
-                this.emit('error', err);
+                this._fail(err);
                 return callback(err);
             }
             let returned = false;
@@ -118,8 +131,8 @@ 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.once('error', err => {
+            this.connection.on('error', err => {
-                this.emit('error', err);
+                this._fail(err);
                 if (returned) {
                     return;
                 }
@@ -128,31 +141,16 @@ class PoolResource extends node_events_1.EventEmitter {
             });
             this.connection.once('end', () => {
                 this.close();
+                returned = true;
+            });
+            this.connection.connect(err => {
                 if (returned) {
                     return;
                 }
-                returned = true;
+                if (err) {
-                const timer = setTimeout(() => {
+                    // a close before the greeting, the 'end' that follows closes this resource
-                    if (returned) {
+                    // and the pool requeues or fails the entry, bounded by maxRequeues
-                        return;
+                    returned = true;
-                    }
-                    // still have not returned, this means we have an unexpected connection close
-                    const err = new Error('Unexpected socket close');
-                    if (this.connection && this.connection.upgrading) {
-                        // starttls connection errors
-                        err.code = errors.ETLS;
-                    }
-                    callback(err);
-                }, 1000);
-                try {
-                    timer.unref();
-                }
-                catch (_E) {
-                    // Ignore. Happens on envs with non-node timer implementation
-                }
-            });
-            this.connection.connect(() => {
-                if (returned) {
                     return;
                 }
                 if (this.auth && (this.connection.allowsAuth || options.forceAuth)) {
@@ -163,7 +161,7 @@ class PoolResource extends node_events_1.EventEmitter {
                         returned = true;
                         if (err) {
                             this.connection.close();
-                            this.emit('error', err);
+                            this._fail(err);
                             return callback(err);
                         }
                         this._connected = true;
@@ -215,7 +213,7 @@ class PoolResource extends node_events_1.EventEmitter {
             this.messages++;
             if (err) {
                 this.connection.close();
-                this.emit('error', err);
+                this._fail(err);
                 return callback(err);
             }
             info.envelope = {
@@ -228,7 +226,7 @@ class PoolResource extends node_events_1.EventEmitter {
                     const err = new Error('Resource exhausted');
                     err.code = errors.EMAXLIMIT;
                     this.connection.close();
-                    this.emit('error', err);
+                    this._fail(err);
                 }
                 else {
                     this.pool._checkRateLimit(() => {

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

@@ -177,31 +177,6 @@ class SMTPTransport extends node_events_1.EventEmitter {
                 connection.close();
                 return callback(err);
             });
-            connection.once('end', () => {
-                if (returned) {
-                    return;
-                }
-                const timer = setTimeout(() => {
-                    if (returned) {
-                        return;
-                    }
-                    returned = true;
-                    cleanupPerCallAuth();
-                    // still have not returned, this means we have an unexpected connection close
-                    const err = new Error('Unexpected socket close');
-                    if (connection && connection.upgrading) {
-                        // starttls connection errors
-                        err.code = errors.ETLS;
-                    }
-                    callback(err);
-                }, 1000);
-                try {
-                    timer.unref();
-                }
-                catch (_E) {
-                    // Ignore. Happens on envs with non-node timer implementation
-                }
-            });
             const sendMessage = () => {
                 const envelope = mail.message.getEnvelope();
                 const messageId = mail.message.messageId();
@@ -221,6 +196,10 @@ class SMTPTransport extends node_events_1.EventEmitter {
                     messageId
                 }, 'Sending message %s to <%s>', messageId, recipients.join(', '));
                 connection.send(envelope, mail.message.createReadStream(), (err, info) => {
+                    if (returned) {
+                        // the connection error handler has already reported this send
+                        return;
+                    }
                     returned = true;
                     cleanupPerCallAuth();
                     connection.close();
@@ -247,10 +226,16 @@ class SMTPTransport extends node_events_1.EventEmitter {
                     }
                 });
             };
-            connection.connect(() => {
+            connection.connect(err => {
                 if (returned) {
                     return;
                 }
+                if (err) {
+                    // the server closed the connection before the greeting
+                    returned = true;
+                    connection.close();
+                    return callback(err);
+                }
                 perCallAuth = this.getAuth(mail.data.auth);
                 if (perCallAuth && (connection.allowsAuth || options.forceAuth)) {
                     connection.login(perCallAuth, err => {
@@ -332,10 +317,15 @@ class SMTPTransport extends node_events_1.EventEmitter {
                 connection.quit();
                 return done(null, true);
             };
-            connection.connect(() => {
+            connection.connect(err => {
                 if (returned) {
                     return;
                 }
+                if (err) {
+                    returned = true;
+                    connection.close();
+                    return done(err);
+                }
                 perCallAuth = this.getAuth({});
                 if (perCallAuth && (connection.allowsAuth || options.forceAuth)) {
                     connection.login(perCallAuth, err => {

node_modules/nodemailer/dist/cjs/xoauth2/index.d.ts

@@ -61,6 +61,8 @@ export interface XOAuth2Options {
     component?: string | undefined;
     /** Extra headers for the token request */
     customHeaders?: OutgoingHttpHeaders | undefined;
+    /** Timeout for the token request in milliseconds, defaults to 60000, 0 disables it */
+    requestTimeout?: number | undefined;
     /** Extra form fields for the token request */
     customParams?: {
         [key: string]: any;

node_modules/nodemailer/dist/cjs/xoauth2/index.js

@@ -74,12 +74,14 @@ class XOAuth2 extends node_stream_1.Stream {
     constructor(options, logger) {
         super();
         this.options = options || {};
+        this.configError = false;
         if (options && options.serviceClient) {
             if (!options.privateKey || !options.user) {
+                // reported through getToken() rather than an 'error' event: the transports forward
+                // that event up to the Mail object, where nothing may be listening
                 const err = new Error('Options "privateKey" and "user" are required for service account!');
                 err.code = errors.EOAUTH2;
-                setImmediate(() => this.emit('error', err));
+                this.configError = err;
-                return;
             }
             const serviceRequestTimeout = Math.min(Math.max(Number(this.options.serviceRequestTimeout) || 0, 0), 3600);
             this.options.serviceRequestTimeout = serviceRequestTimeout || 5 * 60;
@@ -113,6 +115,9 @@ class XOAuth2 extends node_stream_1.Stream {
     getToken(renew, callback) {
         // the error paths hand over the error alone
         const done = callback;
+        if (this.configError) {
+            return done(this.configError);
+        }
         if (!renew && this.accessToken && (!this.expires || this.expires > Date.now())) {
             this.logger.debug({
                 tnx: 'OAUTH2',
@@ -349,7 +354,10 @@ class XOAuth2 extends node_stream_1.Stream {
             method: 'post',
             headers: params.customHeaders,
             body: payload,
-            allowErrorResponse: true
+            allowErrorResponse: true,
+            // unset falls back to the fetch default, a stalled token endpoint would otherwise keep
+            // `renewing` set and queue every later request
+            timeout: params.requestTimeout
         };
         // OAuth2 token endpoints are credential-bearing. src/fetch already
         // validates certs by default; pin rejectUnauthorized:true here so the

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

@@ -240,6 +240,81 @@ function _recoverAddrSpec(data) {
         .filter(part => part)
         .join(' ');
 }
+/**
+ * Takes the RFC 5322 comments out of the contents of an angle-addr.
+ *
+ * The tokenizer tracks a single open operator, so once '<' is open a '(' is plain text and
+ * a comment inside the brackets reached the address verbatim: 'Name <user@example.com(x)evil.com>'
+ * put 'user@example.com(x)evil.com' into the envelope, a value that is no mailbox and that a
+ * receiver stripping the comment reads as 'user@example.comevil.com' (GHSA-g73g-hqqh-jr95).
+ * A comment is folding whitespace, so it is read as a space that splits two atoms and as
+ * nothing next to an '@', the same rule the token walk applies outside the brackets. Quoted
+ * strings and domain literals are copied through untouched, a '(' in there is not a comment.
+ *
+ * @param address Contents of the angle brackets
+ * @return The address with the comments removed, and the text of the comments
+ */
+function _stripAddressComments(address) {
+    const comments = [];
+    let result = '';
+    let comment = '';
+    let depth = 0;
+    let closer = '';
+    // carried along rather than read back off the growing result, which would flatten it on
+    // every comment (see lastChars in _handleAddress)
+    let lastChar = '';
+    for (let i = 0, len = address.length; i < len; i++) {
+        const chr = address.charAt(i);
+        if (depth) {
+            if (chr === '\\' && i < len - 1) {
+                comment += address.charAt(++i);
+            }
+            else if (chr === '(') {
+                depth++;
+                comment += chr;
+            }
+            else if (chr === ')' && !--depth) {
+                comments.push(comment.trim());
+                comment = '';
+                if (lastChar !== '@' && address.charAt(i + 1) !== '@') {
+                    result += ' ';
+                    lastChar = ' ';
+                }
+            }
+            else {
+                comment += chr;
+            }
+            continue;
+        }
+        if (closer) {
+            if (chr === '\\' && closer === '"' && i < len - 1) {
+                result += chr + address.charAt(++i);
+                lastChar = address.charAt(i);
+                continue;
+            }
+            if (chr === closer) {
+                closer = '';
+            }
+        }
+        else if (chr === '"') {
+            closer = '"';
+        }
+        else if (chr === '[') {
+            closer = ']';
+        }
+        else if (chr === '(') {
+            depth = 1;
+            continue;
+        }
+        result += chr;
+        lastChar = chr;
+    }
+    if (depth) {
+        // an unterminated comment runs to the end of the address
+        comments.push(comment.trim());
+    }
+    return { address: result.trim(), comments: comments.filter(text => text) };
+}
 /**
  * Converts tokens for a single address into an address object
  *
@@ -367,6 +442,24 @@ function _handleAddress(tokens, depth) {
         });
     }
     else {
+        // Comments come out of the angle-addr before anything asks whether one was found, so
+        // that brackets holding nothing but a comment read the same as empty ones
+        const addressComments = [];
+        const addressParts = [];
+        for (const part of data.address) {
+            if (part.indexOf('(') < 0) {
+                addressParts.push(part);
+                continue;
+            }
+            const stripped = _stripAddressComments(part);
+            for (const comment of stripped.comments) {
+                addressComments.push(comment);
+            }
+            if (stripped.address) {
+                addressParts.push(stripped.address);
+            }
+        }
+        data.address = addressParts;
         // If no address was found, try to detect one from regular text
         if (!data.address.length && data.text.length) {
             for (let i = data.text.length - 1; i >= 0; i--) {
@@ -433,6 +526,10 @@ function _handleAddress(tokens, depth) {
             data.text = '';
         }
         _recoverAddrSpec(data);
+        // a comment names the mailbox only when nothing else does, as one outside the brackets
+        if (!data.text && addressComments.length) {
+            data.text = addressComments.join(' ');
+        }
         const address = {
             address: data.address || data.text || '',
             name: data.text || data.address || ''

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

@@ -85,13 +85,22 @@ class DKIMSigner {
                 return;
             }
             const key = this.keys[keyPos++];
-            const dkimField = sign(this.headers, this.hashAlgo, this.bodyHash, {
+            let dkimField;
-                domainName: key.domainName,
+            try {
-                keySelector: key.keySelector,
+                dkimField = sign(this.headers, this.hashAlgo, this.bodyHash, {
-                privateKey: key.privateKey,
+                    domainName: key.domainName,
-                headerFieldNames: this.options.headerFieldNames,
+                    keySelector: key.keySelector,
-                skipFields: this.options.skipFields
+                    privateKey: key.privateKey,
-            });
+                    headerFieldNames: this.options.headerFieldNames,
+                    skipFields: this.options.skipFields
+                });
+            }
+            catch (err) {
+                this.hasErrored = true;
+                this.cleanup();
+                this.output.emit('error', err);
+                return;
+            }
             if (dkimField) {
                 this.output.write(Buffer.from(dkimField + '\r\n'));
             }
@@ -191,7 +200,15 @@ class DKIM {
         }
         const signer = new DKIMSigner(options, this.keys, inputStream, output);
         setImmediate(() => {
-            signer.signStream();
+            try {
+                signer.signStream();
+            }
+            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));
+                return;
+            }
             if (writeValue) {
                 setImmediate(() => {
                     inputStream.end(writeValue);

node_modules/nodemailer/dist/esm/dkim/sign.d.ts

@@ -1,4 +1,5 @@
 import crypto from 'node:crypto';
+import type { NodemailerError } from '../errors.js';
 import type { MessageParserHeaderLine } from './message-parser.js';
 /**
  * Private key accepted by crypto.Sign#sign: a PEM string, a Buffer, a KeyObject or an
@@ -45,5 +46,6 @@ export interface DKIMRelaxedHeaders {
 declare function sign(headers: MessageParserHeaderLine[], hashAlgo: string, bodyHash: string, options?: DKIMSignOptions): string | false;
 declare namespace sign {
     var relaxedHeaders: (headers: MessageParserHeaderLine[], fieldNames?: string, skipFields?: string) => DKIMRelaxedHeaders;
+    var unsupportedHashAlgoError: (hashAlgo: string) => NodemailerError;
 }
 export default sign;

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

@@ -1,6 +1,15 @@
 import * as punycode from '../punycode/index.js';
 import * as mimeFuncs from '../mime-funcs/index.js';
 import crypto from 'node:crypto';
+import * as errors from '../errors.js';
+/**
+ * Error for a hashAlgo value the crypto module does not know
+ */
+function unsupportedHashAlgoError(hashAlgo) {
+    const err = new Error('Unsupported DKIM hash algorithm "' + hashAlgo + '"');
+    err.code = errors.ECONFIG;
+    return err;
+}
 /**
  * Returns DKIM signature header line
  *
@@ -25,7 +34,13 @@ function sign(headers, hashAlgo, bodyHash, options) {
     const canonicalizedHeaderData = relaxedHeaders(headers, fieldNames, options.skipFields);
     const dkimHeader = generateDKIMHeader(options.domainName, options.keySelector, canonicalizedHeaderData.fieldNames, hashAlgo, bodyHash);
     canonicalizedHeaderData.headers += 'dkim-signature:' + relaxedHeaderLine(dkimHeader);
-    const signer = crypto.createSign(('rsa-' + hashAlgo).toUpperCase());
+    let signer;
+    try {
+        signer = crypto.createSign(('rsa-' + hashAlgo).toUpperCase());
+    }
+    catch (_E) {
+        throw unsupportedHashAlgoError(hashAlgo);
+    }
     // the header lines are 'binary' strings, so this reproduces the original header bytes
     signer.update(canonicalizedHeaderData.headers, 'latin1');
     let signature;
@@ -38,6 +53,7 @@ function sign(headers, hashAlgo, bodyHash, options) {
     return dkimHeader + signature.replace(/(^.{73}|.{75}(?!\r?\n|\r))/g, '$&\r\n ').trim();
 }
 sign.relaxedHeaders = relaxedHeaders;
+sign.unsupportedHashAlgoError = unsupportedHashAlgoError;
 export default sign;
 function generateDKIMHeader(domainName, keySelector, fieldNames, hashAlgo, bodyHash) {
     // the caller supplied tag values are interpolated straight into the tag list, and none of

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

@@ -25,8 +25,10 @@ export interface FetchOptions {
     tls?: {
         [key: string]: any;
     } | undefined;
-    /** Request timeout in milliseconds */
+    /** Socket inactivity timeout in milliseconds, defaults to 60000, 0 disables it */
     timeout?: number | undefined;
+    /** Maximum size of the (decoded) response body in bytes, defaults to 64 MB, Infinity disables the limit */
+    maxBytes?: number | undefined;
     /** Maximum number of redirects to follow (default 5) */
     maxRedirects?: number | undefined;
     /** Resolve responses with a status code of 300 or above instead of emitting an error */
@@ -47,6 +49,7 @@ export interface FetchResponse extends PassThrough {
 declare function nmfetch(url: string, options?: FetchOptions): FetchResponse;
 declare namespace nmfetch {
     var Cookies: typeof import("./cookies.js").default;
+    var DEFAULT_TIMEOUT: number;
 }
 type CookiesJar = Cookies;
 /**

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

@@ -9,6 +9,10 @@ import net from 'node:net';
 import * as errors from '../errors.js';
 import { isProtoKey } from '../shared/objects.js';
 const MAX_REDIRECTS = 5;
+// a stalled server would otherwise hold the request, and whatever waits on it, open forever
+const DEFAULT_TIMEOUT = 60 * 1000;
+// the body is usually buffered in memory by the caller, so an unbounded download is refused
+const DEFAULT_MAX_BYTES = 64 * 1024 * 1024;
 // Only genuine TLS settings are taken from options.tls. That object reaches us straight
 // from a user supplied attachment (content.tls), so keys like host, port, path, socketPath
 // or lookup would otherwise repoint the request at a destination that never went through
@@ -214,28 +218,22 @@ function nmfetch(url, options) {
         });
         return fetchRes;
     }
-    if (options.timeout) {
+    // reports the first failure of this request on fetchRes and releases the request
-        req.setTimeout(options.timeout, () => {
+    const fail = (err, sourceUrl = url) => {
-            if (finished) {
-                return;
-            }
-            finished = true;
-            req.abort();
-            const err = new Error('Request Timeout');
-            err.code = errors.EFETCH;
-            err.sourceUrl = url;
-            fetchRes.emit('error', err);
-        });
-    }
-    req.on('error', (err) => {
         if (finished) {
             return;
         }
         finished = true;
         err.code = errors.EFETCH;
-        err.sourceUrl = url;
+        err.sourceUrl = sourceUrl;
         fetchRes.emit('error', err);
-    });
+        req.abort();
+    };
+    const timeout = typeof options.timeout === 'number' && options.timeout >= 0 ? options.timeout : DEFAULT_TIMEOUT;
+    if (timeout) {
+        req.setTimeout(timeout, () => fail(new Error('Request Timeout')));
+    }
+    req.on('error', (err) => fail(err));
     req.on('response', res => {
         let inflate;
         if (finished) {
@@ -256,13 +254,7 @@ function nmfetch(url, options) {
             // redirect
             options.redirects++;
             if (options.redirects > options.maxRedirects) {
-                finished = true;
+                return fail(new Error('Maximum redirect count exceeded'));
-                const err = new Error('Maximum redirect count exceeded');
-                err.code = errors.EFETCH;
-                err.sourceUrl = url;
-                fetchRes.emit('error', err);
-                req.abort();
-                return;
             }
             // redirect does not include POST body
             options.method = 'GET';
@@ -282,13 +274,7 @@ function nmfetch(url, options) {
                 // call: that call gets its own `finished` flag and no handle on this
                 // request, so this one would stay open and could emit a second error on
                 // the shared fetchRes once it times out. Callers listen with req.once().
-                finished = true;
+                return fail(new Error('Unsupported protocol for URL ' + redirectUrl), redirectUrl);
-                const err = new Error('Unsupported protocol for URL ' + redirectUrl);
-                err.code = errors.EFETCH;
-                err.sourceUrl = redirectUrl;
-                fetchRes.emit('error', err);
-                req.abort();
-                return;
             }
             // Do not forward credentials when the redirect leaves the original
             // security context: a different host, or a downgrade from https to
@@ -305,41 +291,33 @@ function nmfetch(url, options) {
                     }
                 });
             }
+            // this request is done with, release it so its socket and timeout do not
+            // outlive it and report a late error on the shared fetchRes
+            finished = true;
+            res.resume();
+            req.abort();
             return nmfetch(redirectUrl, options);
         }
         fetchRes.statusCode = res.statusCode;
         fetchRes.headers = res.headers;
         if (res.statusCode >= 300 && !options.allowErrorResponse) {
-            finished = true;
+            return fail(new Error('Invalid status code ' + res.statusCode));
-            const err = new Error('Invalid status code ' + res.statusCode);
-            err.code = errors.EFETCH;
-            err.sourceUrl = url;
-            fetchRes.emit('error', err);
-            req.abort();
-            return;
         }
-        res.on('error', (err) => {
+        res.on('error', (err) => fail(err));
-            if (finished) {
+        const maxBytes = typeof options.maxBytes === 'number' && options.maxBytes > 0 ? options.maxBytes : DEFAULT_MAX_BYTES;
+        const source = inflate || res;
+        let received = 0;
+        source.on('data', (chunk) => {
+            received += chunk.length;
+            if (received <= maxBytes || finished) {
                 return;
             }
-            finished = true;
+            source.unpipe(fetchRes);
-            err.code = errors.EFETCH;
+            fail(new Error('Response size exceeds the allowed ' + maxBytes + ' bytes'));
-            err.sourceUrl = url;
-            fetchRes.emit('error', err);
-            req.abort();
         });
         if (inflate) {
             res.pipe(inflate).pipe(fetchRes);
-            inflate.on('error', (err) => {
+            inflate.on('error', (err) => fail(err));
-                if (finished) {
-                    return;
-                }
-                finished = true;
-                err.code = errors.EFETCH;
-                err.sourceUrl = url;
-                fetchRes.emit('error', err);
-                req.abort();
-            });
         }
         else {
             res.pipe(fetchRes);
@@ -354,11 +332,7 @@ function nmfetch(url, options) {
                 req.write(body);
             }
             catch (err) {
-                finished = true;
+                return fail(err);
-                err.code = errors.EFETCH;
-                err.sourceUrl = url;
-                fetchRes.emit('error', err);
-                return;
             }
         }
         req.end();
@@ -366,4 +340,5 @@ function nmfetch(url, options) {
     return fetchRes;
 }
 nmfetch.Cookies = Cookies;
+nmfetch.DEFAULT_TIMEOUT = DEFAULT_TIMEOUT;
 export default nmfetch;

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

@@ -1,3 +1,3 @@
 export declare const name = "nodemailer";
-export declare const version = "10.0.11";
+export declare const version = "10.0.13";
 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 = '10.0.11';
+export const version = '10.0.13';
 export const homepage = 'https://nodemailer.com/';

node_modules/nodemailer/dist/esm/smtp-connection/data-stream.d.ts

@@ -1,7 +1,8 @@
 import { Transform, type TransformOptions } from 'node:stream';
 /**
  * Escapes dots in the beginning of lines. Ends the stream with <CR><LF>.<CR><LF>
- * Also makes sure that only <CR><LF> sequences are used for linebreaks
+ * Also makes sure that only <CR><LF> sequences are used for linebreaks, bare CR and bare LF
+ * are both turned into <CR><LF>
  *
  * @param options Stream options
  */

node_modules/nodemailer/dist/esm/smtp-connection/data-stream.js

@@ -1,7 +1,13 @@
 import { Transform } from 'node:stream';
+// bytes inserted into the output, shared as they are only ever copied by Buffer.concat
+const INSERT_LF = Buffer.from('\n');
+const INSERT_LF_DOT = Buffer.from('\n.');
+const INSERT_CR = Buffer.from('\r');
+const INSERT_DOT = Buffer.from('.');
 /**
  * Escapes dots in the beginning of lines. Ends the stream with <CR><LF>.<CR><LF>
- * Also makes sure that only <CR><LF> sequences are used for linebreaks
+ * Also makes sure that only <CR><LF> sequences are used for linebreaks, bare CR and bare LF
+ * are both turned into <CR><LF>
  *
  * @param options Stream options
  */
@@ -30,33 +36,35 @@ export default class DataStream extends Transform {
         }
         this.inByteCount += chunk.length;
         for (i = 0, len = chunk.length; i < len; i++) {
-            if (chunk[i] === 0x2e) {
+            const byte = chunk[i];
-                // .
+            const prev = i ? chunk[i - 1] : this.lastByte;
-                if ((i && chunk[i - 1] === 0x0a) || (!i && (!this.lastByte || this.lastByte === 0x0a))) {
+            let insert = false;
-                    buf = chunk.slice(lastPos, i + 1);
+            if (prev === 0x0d && byte !== 0x0a) {
-                    chunks.push(buf);
+                // a bare CR becomes CRLF. A receiver that treats a lone CR as a line end would
-                    chunks.push(Buffer.from('.'));
+                // otherwise see "\r.\r" as the end of the data (SMTP smuggling), so a dot
-                    chunklen += buf.length + 1;
+                // following it is stuffed like at the start of any other line
-                    lastPos = i + 1;
+                insert = byte === 0x2e ? INSERT_LF_DOT : INSERT_LF;
-                }
             }
-            else if (chunk[i] === 0x0a) {
+            else if (byte === 0x0a && prev !== 0x0d) {
-                // \n
+                // a bare LF becomes CRLF
-                if ((i && chunk[i - 1] !== 0x0d) || (!i && this.lastByte !== 0x0d)) {
+                insert = INSERT_CR;
-                    if (i > lastPos) {
+            }
-                        buf = chunk.slice(lastPos, i);
+            else if (byte === 0x2e && (prev === 0x0a || prev === false)) {
-                        chunks.push(buf);
+                // a dot at the start of a line
-                        chunklen += buf.length + 2;
+                insert = INSERT_DOT;
-                    }
+            }
-                    else {
+            if (insert) {
-                        chunklen += 2;
+                if (i > lastPos) {
-                    }
+                    buf = chunk.slice(lastPos, i);
-                    chunks.push(Buffer.from('\r\n'));
+                    chunks.push(buf);
-                    lastPos = i + 1;
+                    chunklen += buf.length;
                 }
+                chunks.push(insert);
+                chunklen += insert.length;
+                lastPos = i;
             }
         }
-        if (chunklen) {
+        if (chunks.length) {
             // add last piece
             if (lastPos < chunk.length) {
                 buf = chunk.slice(lastPos);

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

@@ -26,11 +26,11 @@ export interface SMTPConnectionOptions {
     secured?: boolean | undefined;
     /** Server name for SNI, defaults to host when that is not an IP address */
     servername?: string | undefined;
-    /** Ignore STARTTLS even when the server advertises it */
+    /** Ignore STARTTLS even when the server advertises it, has no effect when requireTLS is set */
     ignoreTLS?: boolean | undefined;
-    /** Force STARTTLS, fail when the server does not support it */
+    /** Force STARTTLS, fail when the server does not support it. Takes precedence over ignoreTLS and opportunisticTLS */
     requireTLS?: boolean | undefined;
-    /** Continue unencrypted when the STARTTLS upgrade fails */
+    /** Continue unencrypted when the STARTTLS upgrade fails, has no effect when requireTLS is set */
     opportunisticTLS?: boolean | undefined;
     /** Name of the client server, sent with EHLO/HELO, CRLF is stripped */
     name?: string | undefined;
@@ -288,8 +288,8 @@ export type SMTPConnectionResponseAction = (str: string) => void;
  *  * **port** - is the port to connect to (defaults to 587 or 465)
  *  * **host** - is the hostname or IP address to connect to (defaults to 'localhost')
  *  * **secure** - use SSL
- *  * **ignoreTLS** - ignore server support for STARTTLS
+ *  * **ignoreTLS** - ignore server support for STARTTLS (has no effect when requireTLS is set)
- *  * **requireTLS** - forces the client to use STARTTLS
+ *  * **requireTLS** - forces the client to use STARTTLS, takes precedence over ignoreTLS and opportunisticTLS
  *  * **name** - the name of the client server
  *  * **localAddress** - outbound address to bind to (see: http://nodejs.org/api/net.html#net_net_connect_options_connectionlistener)
  *  * **greetingTimeout** - Time to wait in ms until greeting message is received from the server (defaults to 30 seconds)

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

@@ -66,8 +66,8 @@ function isPartialLine(line) {
  *  * **port** - is the port to connect to (defaults to 587 or 465)
  *  * **host** - is the hostname or IP address to connect to (defaults to 'localhost')
  *  * **secure** - use SSL
- *  * **ignoreTLS** - ignore server support for STARTTLS
+ *  * **ignoreTLS** - ignore server support for STARTTLS (has no effect when requireTLS is set)
- *  * **requireTLS** - forces the client to use STARTTLS
+ *  * **requireTLS** - forces the client to use STARTTLS, takes precedence over ignoreTLS and opportunisticTLS
  *  * **name** - the name of the client server
  *  * **localAddress** - outbound address to bind to (see: http://nodejs.org/api/net.html#net_net_connect_options_connectionlistener)
  *  * **greetingTimeout** - Time to wait in ms until greeting message is received from the server (defaults to 30 seconds)
@@ -92,6 +92,11 @@ class SMTPConnection extends EventEmitter {
         this.id = crypto.randomBytes(8).toString('base64').replace(/\W/g, '');
         this.stage = 'init';
         this.options = options || {};
+        if (this.options.requireTLS && (this.options.ignoreTLS || this.options.opportunisticTLS)) {
+            // requireTLS wins, a contradictory configuration must not quietly fall back to plaintext.
+            // Copied so the caller's (possibly shared) options object is left as it was
+            this.options = Object.assign({}, this.options, { ignoreTLS: false, opportunisticTLS: false });
+        }
         this.secureConnection = !!this.options.secure;
         this.alreadySecured = !!this.options.secured;
         this.port = Number(this.options.port) || (this.secureConnection ? 465 : 587);
@@ -135,6 +140,8 @@ class SMTPConnection extends EventEmitter {
         this._destroyed = false;
         this._closing = false;
         this._currentDataStream = false;
+        this._pendingSend = false;
+        this._connectCallback = false;
         this._onSocketData = chunk => this._onData(chunk);
         this._onSocketError = error => this._onError(error, 'ESOCKET', false, 'CONN');
         this._onSocketClose = () => this._onClose();
@@ -149,7 +156,9 @@ class SMTPConnection extends EventEmitter {
      */
     connect(connectCallback) {
         if (typeof connectCallback === 'function') {
+            this._connectCallback = connectCallback;
             this.once('connect', () => {
+                this._connectCallback = false;
                 this.logger.debug({
                     tnx: 'smtp'
                 }, 'SMTP handshake finished');
@@ -381,6 +390,16 @@ class SMTPConnection extends EventEmitter {
             }
             this._currentDataStream = false;
         }
+        // Detach from the message stream as well. The listener is swapped for a no-op rather than
+        // removed, a stream destroyed with an error later on 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);
+            }
+            this._pendingSend = false;
+        }
         if (socket && !socket.destroyed) {
             try {
                 // Clear socket timeout to prevent timer leaks
@@ -568,6 +587,9 @@ class SMTPConnection extends EventEmitter {
                 return;
             }
             returned = true;
+            if (this._pendingSend && this._pendingSend.callback === callback) {
+                this._pendingSend = false;
+            }
             done(err, info);
         };
         if (!message) {
@@ -584,9 +606,16 @@ class SMTPConnection extends EventEmitter {
             });
             return;
         }
+        const pendingSend = {
+            callback,
+            stream: false,
+            onStreamError: err => callback(this._formatError(err, 'ESTREAM', false, 'API'))
+        };
         if (typeof message.on === 'function') {
-            message.on('error', err => callback(this._formatError(err, 'ESTREAM', false, 'API')));
+            pendingSend.stream = message;
+            pendingSend.stream.on('error', pendingSend.onStreamError);
         }
+        this._pendingSend = pendingSend;
         const startTime = Date.now();
         this._setEnvelope(envelope, (err, info) => {
             if (err) {
@@ -779,8 +808,14 @@ class SMTPConnection extends EventEmitter {
         else {
             this.logger.error(data, 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
+        const pendingSend = this._pendingSend;
         this.emit('error', err);
         this.close();
+        if (pendingSend) {
+            pendingSend.callback(err);
+        }
     }
     /** @internal */
     _formatError(message, type, response, command) {
@@ -826,14 +861,25 @@ class SMTPConnection extends EventEmitter {
         this.logger.info({
             tnx: 'network'
         }, 'Connection closed');
+        // the unterminated remainder is only reported as a reply (and so gives the error a responseCode)
+        // when it starts like a complete failure reply, not for a fragment such as "55" or a 250
+        const failureResponse = typeof serverResponse === 'string' && /^[45]\d{2}[ -]/.test(serverResponse) ? serverResponse : false;
         if (this.upgrading && !this._destroyed) {
-            return this._onError(new Error('Connection closed unexpectedly'), 'ETLS', serverResponse, 'CONN');
+            return this._onError(new Error('Connection closed unexpectedly'), 'ETLS', failureResponse, 'CONN');
         }
-        else if (![this._actionGreeting, this.close].includes(this._responseActions[0]) && !this._destroyed) {
+        if (!failureResponse && this._responseActions[0] === this._actionGreeting && this._connectCallback && !this._destroyed) {
-            return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', serverResponse, 'CONN');
+            // A silent close before the greeting is handed to the connect() callback rather than
+            // emitted as 'error', callers that never saw an error for it must not start throwing one
+            const connectCallback = this._connectCallback;
+            this._connectCallback = false;
+            const err = this._formatError(new Error('Connection closed unexpectedly'), 'ECONNECTION', false, 'CONN');
+            this.logger.warn({ tnx: 'network' }, err.message);
+            connectCallback(err);
+            this.close();
+            return;
         }
-        else if (/^[45]\d{2}\b/.test(serverResponse)) {
+        if (failureResponse || (this._responseActions[0] !== this.close && !this._destroyed)) {
-            return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', serverResponse, 'CONN');
+            return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', failureResponse, 'CONN');
         }
         this._destroy();
     }
@@ -1310,21 +1356,25 @@ class SMTPConnection extends EventEmitter {
         if (/[ -]AUTH\b/i.test(str)) {
             this.allowsAuth = true;
         }
-        // Detect if the server supports PLAIN auth
+        // Detect the advertised SASL mechanisms. The list is split into whole tokens rather
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)PLAIN/i.test(str)) {
+        // than searched for each name with a pattern: the patterns this replaced let two
-            this._supportedAuth.push('PLAIN');
+        // whitespace runs overlap and backtracked quadratically over an AUTH line padded with
+        // spaces, so a hostile server could stall the event loop from its EHLO reply
+        // (GHSA-4ffr-jq9g-5ffx).
+        const authMechanisms = new Set();
+        for (const line of this._ehloLines) {
+            const authMatch = /^AUTH[\s=](.*)/i.exec(line);
+            if (authMatch) {
+                for (const mechanism of authMatch[1].split(/[\s=]+/)) {
+                    authMechanisms.add(mechanism.toUpperCase());
+                }
+            }
         }
-        // Detect if the server supports LOGIN auth
+        // listed in order of preference, the first one the credentials allow is used
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)LOGIN/i.test(str)) {
+        for (const mechanism of ['PLAIN', 'LOGIN', 'CRAM-MD5', 'XOAUTH2']) {
-            this._supportedAuth.push('LOGIN');
+            if (authMechanisms.has(mechanism)) {
-        }
+                this._supportedAuth.push(mechanism);
-        // Detect if the server supports CRAM-MD5 auth
+            }
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)CRAM-MD5/i.test(str)) {
-            this._supportedAuth.push('CRAM-MD5');
-        }
-        // Detect if the server supports XOAUTH2 auth
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)XOAUTH2/i.test(str)) {
-            this._supportedAuth.push('XOAUTH2');
         }
         // Detect if the server supports SIZE extensions (and the max allowed size)
         if ((match = str.match(/[ -]SIZE(?:[ \t]+(\d+))?/im))) {
@@ -1584,7 +1634,11 @@ class SMTPConnection extends EventEmitter {
                 this._sendCommand('DATA');
             }
             else {
-                err = this._formatError("Can't send mail - all recipients were rejected", 'EENVELOPE', str, 'RCPT TO');
+                // 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;
+                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);

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

@@ -17,7 +17,7 @@ export interface SMTPPoolOptions extends SMTPTransportOptions {
     rateLimit?: number | undefined;
     /** Time window for rateLimit in milliseconds, defaults to 1000 */
     rateDelta?: number | undefined;
-    /** How many times a message is requeued when its connection closes while sending, unlimited when not set or negative */
+    /** How many times a message is requeued when its connection closes while sending, defaults to 5, a negative value means unlimited */
     maxRequeues?: number | undefined;
 }
 /**
@@ -26,6 +26,7 @@ export interface SMTPPoolOptions extends SMTPTransportOptions {
 export type SMTPPoolResolvedOptions = SMTPPoolOptions & {
     maxConnections: number;
     maxMessages: number;
+    maxRequeues: number;
 };
 /**
  * Result of a message sent through the pool, same as for the SMTP transport

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

@@ -5,6 +5,10 @@ import wellKnown from '../well-known/index.js';
 import * as shared from '../shared/index.js';
 import * as errors from '../errors.js';
 import * as packageData from '../package-info.js';
+/** First delay before a requeued message is retried, doubled on every further requeue */
+const REQUEUE_BASE_DELAY = 50;
+/** Upper bound for the requeue delay */
+const REQUEUE_MAX_DELAY = 2000;
 /**
  * Creates a SMTP pool transport object for Nodemailer
  *
@@ -36,6 +40,8 @@ class SMTPPool extends EventEmitter {
         );
         this.options.maxConnections = this.options.maxConnections || 5;
         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;
         this.logger = shared.getLogger(this.options, {
             component: this.options.component || 'smtp-pool'
         });
@@ -79,6 +85,10 @@ class SMTPPool extends EventEmitter {
      */
     send(mail, callback) {
         if (this._closed) {
+            // Mail.sendMail ignores the return value, so without a callback its promise would never settle
+            const err = new Error('Connection pool was closed');
+            err.code = errors.ECONNECTION;
+            setImmediate(() => callback(err));
             return false;
         }
         this._queue.push({
@@ -292,15 +302,22 @@ class SMTPPool extends EventEmitter {
                 // Note that we must wait a bit.. because the callback of the 'error' handler might be called
                 // in the next event loop
                 setTimeout(() => {
+                    let delay = 0;
                     if (connection.queueEntry) {
                         if (this._shouldRequeuOnConnectionClose(connection.queueEntry)) {
-                            this._requeueEntryOnConnectionClose(connection);
+                            delay = this._requeueEntryOnConnectionClose(connection);
                         }
                         else {
                             this._failDeliveryOnConnectionClose(connection);
                         }
                     }
-                    this._continueProcessing();
+                    if (delay) {
+                        // back off, a server that keeps dropping connections is not hammered
+                        setTimeout(() => this._continueProcessing(), delay);
+                    }
+                    else {
+                        this._continueProcessing();
+                    }
                 }, 50);
             }
             else {
@@ -315,7 +332,7 @@ class SMTPPool extends EventEmitter {
     }
     /** @internal */
     _shouldRequeuOnConnectionClose(queueEntry) {
-        if (this.options.maxRequeues === undefined || this.options.maxRequeues < 0) {
+        if (this.options.maxRequeues < 0) {
             return true;
         }
         return queueEntry.requeueAttempts < this.options.maxRequeues;
@@ -324,7 +341,9 @@ class SMTPPool extends EventEmitter {
     _failDeliveryOnConnectionClose(connection) {
         if (connection.queueEntry && connection.queueEntry.callback) {
             try {
-                connection.queueEntry.callback(new Error('Reached maximum number of retries after connection was closed'));
+                const err = new Error('Reached maximum number of retries after connection was closed');
+                err.code = errors.ECONNECTION;
+                connection.queueEntry.callback(err);
             }
             catch (E) {
                 this.logger.error({
@@ -339,6 +358,7 @@ class SMTPPool extends EventEmitter {
     }
     /** @internal */
     _requeueEntryOnConnectionClose(connection) {
+        const delay = Math.min(REQUEUE_BASE_DELAY * 2 ** connection.queueEntry.requeueAttempts, REQUEUE_MAX_DELAY);
         connection.queueEntry.requeueAttempts += 1;
         this.logger.debug({
             tnx: 'pool',
@@ -348,6 +368,7 @@ class SMTPPool extends EventEmitter {
         }, 'Re-queued message <%s> for #%s. Attempt: #%s', connection.queueEntry.messageId, connection.id, connection.queueEntry.requeueAttempts);
         this._queue.unshift(connection.queueEntry);
         connection.queueEntry = false;
+        return delay;
     }
     /**
      * Continue to process message if the pool hasn't closed
@@ -468,10 +489,15 @@ class SMTPPool extends EventEmitter {
                 connection.quit();
                 return done(null, true);
             };
-            connection.connect(() => {
+            connection.connect(err => {
                 if (returned) {
                     return;
                 }
+                if (err) {
+                    returned = true;
+                    connection.close();
+                    return done(err);
+                }
                 if (auth && (connection.allowsAuth || options.forceAuth)) {
                     connection.login(auth, err => {
                         if (returned) {

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

@@ -28,7 +28,7 @@ export default class PoolResource extends EventEmitter {
                         method: 'XOAUTH2'
                     };
                     oauth2.on('token', (token) => this.pool.mailer.emit('token', token));
-                    oauth2.on('error', err => this.emit('error', err));
+                    oauth2.on('error', err => this._fail(err));
                     break;
                 }
                 default:
@@ -51,6 +51,19 @@ export default class PoolResource extends EventEmitter {
         this._connected = false;
         this.messages = 0;
         this.available = true;
+        this._failed = false;
+    }
+    /**
+     * Emits 'error' for the first failure only. A dead resource can report the same failure more
+     * than once (the connection error, then the send callback), the pool handles it once
+     * @internal
+     */
+    _fail(err) {
+        if (this._failed) {
+            return;
+        }
+        this._failed = true;
+        this.emit('error', err);
     }
     /**
      * Initiates a connection to the SMTP server
@@ -63,7 +76,7 @@ export default class PoolResource extends EventEmitter {
                 // 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
                 // login does
-                this.emit('error', err);
+                this._fail(err);
                 return callback(err);
             }
             let returned = false;
@@ -80,8 +93,8 @@ export default class PoolResource extends EventEmitter {
                 options = Object.assign(assign(false, options), socketOptions);
             }
             this.connection = new SMTPConnection(options);
-            this.connection.once('error', err => {
+            this.connection.on('error', err => {
-                this.emit('error', err);
+                this._fail(err);
                 if (returned) {
                     return;
                 }
@@ -90,31 +103,16 @@ export default class PoolResource extends EventEmitter {
             });
             this.connection.once('end', () => {
                 this.close();
+                returned = true;
+            });
+            this.connection.connect(err => {
                 if (returned) {
                     return;
                 }
-                returned = true;
+                if (err) {
-                const timer = setTimeout(() => {
+                    // a close before the greeting, the 'end' that follows closes this resource
-                    if (returned) {
+                    // and the pool requeues or fails the entry, bounded by maxRequeues
-                        return;
+                    returned = true;
-                    }
-                    // still have not returned, this means we have an unexpected connection close
-                    const err = new Error('Unexpected socket close');
-                    if (this.connection && this.connection.upgrading) {
-                        // starttls connection errors
-                        err.code = errors.ETLS;
-                    }
-                    callback(err);
-                }, 1000);
-                try {
-                    timer.unref();
-                }
-                catch (_E) {
-                    // Ignore. Happens on envs with non-node timer implementation
-                }
-            });
-            this.connection.connect(() => {
-                if (returned) {
                     return;
                 }
                 if (this.auth && (this.connection.allowsAuth || options.forceAuth)) {
@@ -125,7 +123,7 @@ export default class PoolResource extends EventEmitter {
                         returned = true;
                         if (err) {
                             this.connection.close();
-                            this.emit('error', err);
+                            this._fail(err);
                             return callback(err);
                         }
                         this._connected = true;
@@ -177,7 +175,7 @@ export default class PoolResource extends EventEmitter {
             this.messages++;
             if (err) {
                 this.connection.close();
-                this.emit('error', err);
+                this._fail(err);
                 return callback(err);
             }
             info.envelope = {
@@ -190,7 +188,7 @@ export default class PoolResource extends EventEmitter {
                     const err = new Error('Resource exhausted');
                     err.code = errors.EMAXLIMIT;
                     this.connection.close();
-                    this.emit('error', err);
+                    this._fail(err);
                 }
                 else {
                     this.pool._checkRateLimit(() => {

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

@@ -139,31 +139,6 @@ class SMTPTransport extends EventEmitter {
                 connection.close();
                 return callback(err);
             });
-            connection.once('end', () => {
-                if (returned) {
-                    return;
-                }
-                const timer = setTimeout(() => {
-                    if (returned) {
-                        return;
-                    }
-                    returned = true;
-                    cleanupPerCallAuth();
-                    // still have not returned, this means we have an unexpected connection close
-                    const err = new Error('Unexpected socket close');
-                    if (connection && connection.upgrading) {
-                        // starttls connection errors
-                        err.code = errors.ETLS;
-                    }
-                    callback(err);
-                }, 1000);
-                try {
-                    timer.unref();
-                }
-                catch (_E) {
-                    // Ignore. Happens on envs with non-node timer implementation
-                }
-            });
             const sendMessage = () => {
                 const envelope = mail.message.getEnvelope();
                 const messageId = mail.message.messageId();
@@ -183,6 +158,10 @@ class SMTPTransport extends EventEmitter {
                     messageId
                 }, 'Sending message %s to <%s>', messageId, recipients.join(', '));
                 connection.send(envelope, mail.message.createReadStream(), (err, info) => {
+                    if (returned) {
+                        // the connection error handler has already reported this send
+                        return;
+                    }
                     returned = true;
                     cleanupPerCallAuth();
                     connection.close();
@@ -209,10 +188,16 @@ class SMTPTransport extends EventEmitter {
                     }
                 });
             };
-            connection.connect(() => {
+            connection.connect(err => {
                 if (returned) {
                     return;
                 }
+                if (err) {
+                    // the server closed the connection before the greeting
+                    returned = true;
+                    connection.close();
+                    return callback(err);
+                }
                 perCallAuth = this.getAuth(mail.data.auth);
                 if (perCallAuth && (connection.allowsAuth || options.forceAuth)) {
                     connection.login(perCallAuth, err => {
@@ -294,10 +279,15 @@ class SMTPTransport extends EventEmitter {
                 connection.quit();
                 return done(null, true);
             };
-            connection.connect(() => {
+            connection.connect(err => {
                 if (returned) {
                     return;
                 }
+                if (err) {
+                    returned = true;
+                    connection.close();
+                    return done(err);
+                }
                 perCallAuth = this.getAuth({});
                 if (perCallAuth && (connection.allowsAuth || options.forceAuth)) {
                     connection.login(perCallAuth, err => {

node_modules/nodemailer/dist/esm/xoauth2/index.d.ts

@@ -61,6 +61,8 @@ export interface XOAuth2Options {
     component?: string | undefined;
     /** Extra headers for the token request */
     customHeaders?: OutgoingHttpHeaders | undefined;
+    /** Timeout for the token request in milliseconds, defaults to 60000, 0 disables it */
+    requestTimeout?: number | undefined;
     /** Extra form fields for the token request */
     customParams?: {
         [key: string]: any;

node_modules/nodemailer/dist/esm/xoauth2/index.js

@@ -36,12 +36,14 @@ class XOAuth2 extends Stream {
     constructor(options, logger) {
         super();
         this.options = options || {};
+        this.configError = false;
         if (options && options.serviceClient) {
             if (!options.privateKey || !options.user) {
+                // reported through getToken() rather than an 'error' event: the transports forward
+                // that event up to the Mail object, where nothing may be listening
                 const err = new Error('Options "privateKey" and "user" are required for service account!');
                 err.code = errors.EOAUTH2;
-                setImmediate(() => this.emit('error', err));
+                this.configError = err;
-                return;
             }
             const serviceRequestTimeout = Math.min(Math.max(Number(this.options.serviceRequestTimeout) || 0, 0), 3600);
             this.options.serviceRequestTimeout = serviceRequestTimeout || 5 * 60;
@@ -75,6 +77,9 @@ class XOAuth2 extends Stream {
     getToken(renew, callback) {
         // the error paths hand over the error alone
         const done = callback;
+        if (this.configError) {
+            return done(this.configError);
+        }
         if (!renew && this.accessToken && (!this.expires || this.expires > Date.now())) {
             this.logger.debug({
                 tnx: 'OAUTH2',
@@ -311,7 +316,10 @@ class XOAuth2 extends Stream {
             method: 'post',
             headers: params.customHeaders,
             body: payload,
-            allowErrorResponse: true
+            allowErrorResponse: true,
+            // unset falls back to the fetch default, a stalled token endpoint would otherwise keep
+            // `renewing` set and queue every later request
+            timeout: params.requestTimeout
         };
         // OAuth2 token endpoints are credential-bearing. src/fetch already
         // validates certs by default; pin rejectUnauthorized:true here so the

node_modules/nodemailer/package.json

@@ -1,6 +1,6 @@
 {
     "name": "nodemailer",
-    "version": "10.0.11",
+    "version": "10.0.13",
     "description": "Easy as cake e-mail sending from your Node.js applications",
     "type": "module",
     "main": "./dist/cjs/nodemailer.js",
@@ -151,24 +151,24 @@
     },
     "homepage": "https://nodemailer.com/",
     "devDependencies": {
-        "@aws-sdk/client-sesv2": "3.1141.0",
+        "@aws-sdk/client-sesv2": "3.1143.0",
         "@types/node": "20.19.43",
         "bunyan": "1.8.15",
         "c8": "12.0.0",
         "eslint": "10.11.0",
         "eslint-config-prettier": "10.1.8",
         "globals": "17.12.0",
-        "libbase64": "1.3.0",
+        "libbase64": "1.3.1",
-        "libmime": "5.4.4",
+        "libmime": "5.4.6",
-        "libqp": "2.1.1",
+        "libqp": "2.1.2",
         "mailauth": "7.1.0",
         "prettier": "3.9.9",
         "proxy": "1.0.2",
         "proxy-test-server": "1.0.0",
-        "smtp-server": "3.19.13",
+        "smtp-server": "3.19.15",
         "tsx": "4.23.15",
         "typescript": "6.0.3",
-        "typescript-eslint": "8.70.1"
+        "typescript-eslint": "8.71.0"
     },
     "engines": {
         "node": ">=20.0.0"