nodemailer 7.0.13 → 8.0.1

package/CHANGELOG.md

@@ -1,5 +1,28 @@
 # CHANGELOG
 
+## [8.0.1](https://github.com/nodemailer/nodemailer/compare/v8.0.0...v8.0.1) (2026-02-07)
+
+
+### Bug Fixes
+
+* absorb TLS errors during socket teardown ([7f8dde4](https://github.com/nodemailer/nodemailer/commit/7f8dde41438c66b8311e888fa5f8c518fcaba6f1))
+* absorb TLS errors during socket teardown ([381f628](https://github.com/nodemailer/nodemailer/commit/381f628d55e62bb3131bd2a452fa1ce00bc48aea))
+* Add Gmail Workspace service configuration ([#1787](https://github.com/nodemailer/nodemailer/issues/1787)) ([dc97ede](https://github.com/nodemailer/nodemailer/commit/dc97ede417b3030b311771541b1f17f5ca76bcbf))
+
+## [8.0.0](https://github.com/nodemailer/nodemailer/compare/v7.0.13...v8.0.0) (2026-02-04)
+
+
+### ⚠ BREAKING CHANGES
+
+* Error code 'NoAuth' renamed to 'ENOAUTH'
+
+### Bug Fixes
+
+* add connection fallback to alternative DNS addresses ([e726d6f](https://github.com/nodemailer/nodemailer/commit/e726d6f44aa7ca14e943d4303243cb5494b09c75))
+* centralize and standardize error codes ([45062ce](https://github.com/nodemailer/nodemailer/commit/45062ce7a4705f3e63c5d9e606547f4d99fd29b5))
+* harden DNS fallback against race conditions and cleanup issues ([4fa3c63](https://github.com/nodemailer/nodemailer/commit/4fa3c63a1f36aefdbaea7f57a133adc458413a47))
+* improve socket cleanup to prevent potential memory leaks ([6069fdc](https://github.com/nodemailer/nodemailer/commit/6069fdcff68a3eef9a9bb16b2bf5ddb924c02091))
+
 ## [7.0.13](https://github.com/nodemailer/nodemailer/compare/v7.0.12...v7.0.13) (2026-01-27)
 
 

package/lib/errors.js

@@ -0,0 +1,61 @@
+'use strict';
+
+/**
+ * Nodemailer Error Codes
+ *
+ * Centralized error code definitions for consistent error handling.
+ *
+ * Usage:
+ *   const errors = require('./errors');
+ *   let err = new Error('Connection closed');
+ *   err.code = errors.ECONNECTION;
+ */
+
+/**
+ * Error code descriptions for documentation and debugging
+ */
+const ERROR_CODES = {
+    // Connection errors
+    ECONNECTION: 'Connection closed unexpectedly',
+    ETIMEDOUT: 'Connection or operation timed out',
+    ESOCKET: 'Socket-level error',
+    EDNS: 'DNS resolution failed',
+
+    // TLS/Security errors
+    ETLS: 'TLS handshake or STARTTLS failed',
+    EREQUIRETLS: 'REQUIRETLS not supported by server (RFC 8689)',
+
+    // Protocol errors
+    EPROTOCOL: 'Invalid SMTP server response',
+    EENVELOPE: 'Invalid mail envelope (sender or recipients)',
+    EMESSAGE: 'Message delivery error',
+    ESTREAM: 'Stream processing error',
+
+    // Authentication errors
+    EAUTH: 'Authentication failed',
+    ENOAUTH: 'Authentication credentials not provided',
+    EOAUTH2: 'OAuth2 token generation or refresh error',
+
+    // Resource errors
+    EMAXLIMIT: 'Pool resource limit reached (max messages per connection)',
+
+    // Transport-specific errors
+    ESENDMAIL: 'Sendmail command error',
+    ESES: 'AWS SES transport error',
+
+    // Configuration and access errors
+    ECONFIG: 'Invalid configuration',
+    EPROXY: 'Proxy connection error',
+    EFILEACCESS: 'File access rejected (disableFileAccess is set)',
+    EURLACCESS: 'URL access rejected (disableUrlAccess is set)',
+    EFETCH: 'HTTP fetch error'
+};
+
+// Export error codes as string constants and the full definitions object
+module.exports = Object.keys(ERROR_CODES).reduce(
+    (exports, code) => {
+        exports[code] = code;
+        return exports;
+    },
+    { ERROR_CODES }
+);

package/lib/fetch/index.js

@@ -8,6 +8,7 @@ const PassThrough = require('stream').PassThrough;
 const Cookies = require('./cookies');
 const packageData = require('../../package.json');
 const net = require('net');
+const errors = require('../errors');
 
 const MAX_REDIRECTS = 5;
 
@@ -76,7 +77,7 @@ function nmfetch(url, options) {
                     return;
                 }
                 finished = true;
-                err.type = 'FETCH';
+                err.code = errors.EFETCH;
                 err.sourceUrl = url;
                 fetchRes.emit('error', err);
             });
@@ -99,7 +100,7 @@ function nmfetch(url, options) {
                         return;
                     }
                     finished = true;
-                    E.type = 'FETCH';
+                    E.code = errors.EFETCH;
                     E.sourceUrl = url;
                     fetchRes.emit('error', E);
                     return;
@@ -147,7 +148,7 @@ function nmfetch(url, options) {
     } catch (E) {
         finished = true;
         setImmediate(() => {
-            E.type = 'FETCH';
+            E.code = errors.EFETCH;
             E.sourceUrl = url;
             fetchRes.emit('error', E);
         });
@@ -162,7 +163,7 @@ function nmfetch(url, options) {
             finished = true;
             req.abort();
             let err = new Error('Request Timeout');
-            err.type = 'FETCH';
+            err.code = errors.EFETCH;
             err.sourceUrl = url;
             fetchRes.emit('error', err);
         });
@@ -173,7 +174,7 @@ function nmfetch(url, options) {
             return;
         }
         finished = true;
-        err.type = 'FETCH';
+        err.code = errors.EFETCH;
         err.sourceUrl = url;
         fetchRes.emit('error', err);
     });
@@ -204,7 +205,7 @@ function nmfetch(url, options) {
             if (options.redirects > options.maxRedirects) {
                 finished = true;
                 let err = new Error('Maximum redirect count exceeded');
-                err.type = 'FETCH';
+                err.code = errors.EFETCH;
                 err.sourceUrl = url;
                 fetchRes.emit('error', err);
                 req.abort();
@@ -222,7 +223,7 @@ function nmfetch(url, options) {
         if (res.statusCode >= 300 && !options.allowErrorResponse) {
             finished = true;
             let err = new Error('Invalid status code ' + res.statusCode);
-            err.type = 'FETCH';
+            err.code = errors.EFETCH;
             err.sourceUrl = url;
             fetchRes.emit('error', err);
             req.abort();
@@ -234,7 +235,7 @@ function nmfetch(url, options) {
                 return;
             }
             finished = true;
-            err.type = 'FETCH';
+            err.code = errors.EFETCH;
             err.sourceUrl = url;
             fetchRes.emit('error', err);
             req.abort();
@@ -247,7 +248,7 @@ function nmfetch(url, options) {
                     return;
                 }
                 finished = true;
-                err.type = 'FETCH';
+                err.code = errors.EFETCH;
                 err.sourceUrl = url;
                 fetchRes.emit('error', err);
                 req.abort();
@@ -267,7 +268,7 @@ function nmfetch(url, options) {
                 }
             } catch (err) {
                 finished = true;
-                err.type = 'FETCH';
+                err.code = errors.EFETCH;
                 err.sourceUrl = url;
                 fetchRes.emit('error', err);
                 return;

package/lib/mailer/index.js

@@ -6,6 +6,7 @@ const mimeTypes = require('../mime-funcs/mime-types');
 const MailComposer = require('../mail-composer');
 const DKIM = require('../dkim');
 const httpProxyClient = require('../smtp-connection/http-proxy-client');
+const errors = require('../errors');
 const util = require('util');
 const urllib = require('url');
 const packageData = require('../../package.json');
@@ -337,7 +338,9 @@ class Mail extends EventEmitter {
                 case 'socks4':
                 case 'socks4a': {
                     if (!this.meta.has('proxy_socks_module')) {
-                        return callback(new Error('Socks module not loaded'));
+                        let err = new Error('Socks module not loaded');
+                        err.code = errors.EPROXY;
+                        return callback(err);
                     }
                     let connect = ipaddress => {
                         let proxyV2 = !!this.meta.get('proxy_socks_module').SocksClient;
@@ -394,7 +397,9 @@ class Mail extends EventEmitter {
                     });
                 }
             }
-            callback(new Error('Unknown proxy configuration'));
+            let err = new Error('Unknown proxy configuration');
+            err.code = errors.EPROXY;
+            callback(err);
         };
     }
 

package/lib/mime-node/index.js

@@ -13,6 +13,7 @@ const qp = require('../qp');
 const base64 = require('../base64');
 const addressparser = require('../addressparser');
 const nmfetch = require('../fetch');
+const errors = require('../errors');
 const LastNewline = require('./last-newline');
 
 const LeWindows = require('./le-windows');
@@ -979,7 +980,11 @@ class MimeNode {
         } else if (content && typeof content.path === 'string' && !content.href) {
             if (this.disableFileAccess) {
                 contentStream = new PassThrough();
-                setImmediate(() => contentStream.emit('error', new Error('File access rejected for ' + content.path)));
+                setImmediate(() => {
+                    let err = new Error('File access rejected for ' + content.path);
+                    err.code = errors.EFILEACCESS;
+                    contentStream.emit('error', err);
+                });
                 return contentStream;
             }
             // read file
@@ -987,7 +992,11 @@ class MimeNode {
         } else if (content && typeof content.href === 'string') {
             if (this.disableUrlAccess) {
                 contentStream = new PassThrough();
-                setImmediate(() => contentStream.emit('error', new Error('Url access rejected for ' + content.href)));
+                setImmediate(() => {
+                    let err = new Error('Url access rejected for ' + content.href);
+                    err.code = errors.EURLACCESS;
+                    contentStream.emit('error', err);
+                });
                 return contentStream;
             }
             // fetch URL

package/lib/nodemailer.js

@@ -8,6 +8,7 @@ const SendmailTransport = require('./sendmail-transport');
 const StreamTransport = require('./stream-transport');
 const JSONTransport = require('./json-transport');
 const SESTransport = require('./ses-transport');
+const errors = require('./errors');
 const nmfetch = require('./fetch');
 const packageData = require('../package.json');
 
@@ -49,7 +50,7 @@ module.exports.createTransport = function (transporter, defaults) {
                 let error = new Error(
                     'Using legacy SES configuration, expecting @aws-sdk/client-sesv2, see https://nodemailer.com/transports/ses/'
                 );
-                error.code = 'LegacyConfig';
+                error.code = errors.ECONFIG;
                 throw error;
             }
             transporter = new SESTransport(options);

package/lib/sendmail-transport/index.js

@@ -3,6 +3,7 @@
 const spawn = require('child_process').spawn;
 const packageData = require('../../package.json');
 const shared = require('../shared');
+const errors = require('../errors');
 
 /**
  * Generates a Transport object for Sendmail
@@ -72,7 +73,9 @@ class SendmailTransport {
             .concat(envelope.to || [])
             .some(addr => /^-/.test(addr));
         if (hasInvalidAddresses) {
-            return done(new Error('Can not send mail. Invalid envelope addresses.'));
+            let err = new Error('Can not send mail. Invalid envelope addresses.');
+            err.code = errors.ESENDMAIL;
+            return done(err);
         }
 
         if (this.args) {
@@ -141,6 +144,7 @@ class SendmailTransport {
                 } else {
                     err = new Error('Sendmail exited with code ' + code);
                 }
+                err.code = errors.ESENDMAIL;
 
                 this.logger.error(
                     {
@@ -202,7 +206,9 @@ class SendmailTransport {
 
             sourceStream.pipe(sendmail.stdin);
         } else {
-            return callback(new Error('sendmail was not found'));
+            let err = new Error('sendmail was not found');
+            err.code = errors.ESENDMAIL;
+            return callback(err);
         }
     }
 }

package/lib/shared/index.js

@@ -82,15 +82,22 @@ const formatDNSValue = (value, extra) => {
         return Object.assign({}, extra || {});
     }
 
+    let addresses = value.addresses || [];
+
+    // Select a random address from available addresses, or null if none
+    let host = null;
+    if (addresses.length === 1) {
+        host = addresses[0];
+    } else if (addresses.length > 1) {
+        host = addresses[Math.floor(Math.random() * addresses.length)];
+    }
+
     return Object.assign(
         {
             servername: value.servername,
-            host:
-                !value.addresses || !value.addresses.length
-                    ? null
-                    : value.addresses.length === 1
-                      ? value.addresses[0]
-                      : value.addresses[Math.floor(Math.random() * value.addresses.length)]
+            host,
+            // Include all addresses for connection fallback support
+            _addresses: addresses
         },
         extra || {}
     );
@@ -151,46 +158,51 @@ module.exports.resolveHostname = (options, callback) => {
         }
     }
 
+    // Resolve both IPv4 and IPv6 addresses for fallback support
+    let ipv4Addresses = [];
+    let ipv6Addresses = [];
+    let ipv4Error = null;
+    let ipv6Error = null;
+
     resolver(4, options.host, options, (err, addresses) => {
         if (err) {
-            if (cached) {
+            ipv4Error = err;
+        } else {
+            ipv4Addresses = addresses || [];
+        }
+
+        resolver(6, options.host, options, (err, addresses) => {
+            if (err) {
+                ipv6Error = err;
+            } else {
+                ipv6Addresses = addresses || [];
+            }
+
+            // Combine addresses: IPv4 first, then IPv6
+            let allAddresses = ipv4Addresses.concat(ipv6Addresses);
+
+            if (allAddresses.length) {
+                let value = {
+                    addresses: allAddresses,
+                    servername: options.servername || options.host
+                };
+
                 dnsCache.set(options.host, {
-                    value: cached.value,
+                    value,
                     expires: Date.now() + (options.dnsTtl || DNS_TTL)
                 });
 
                 return callback(
                     null,
-                    formatDNSValue(cached.value, {
-                        cached: true,
-                        error: err
+                    formatDNSValue(value, {
+                        cached: false
                     })
                 );
             }
-            return callback(err);
-        }
-
-        if (addresses && addresses.length) {
-            let value = {
-                addresses,
-                servername: options.servername || options.host
-            };
 
-            dnsCache.set(options.host, {
-                value,
-                expires: Date.now() + (options.dnsTtl || DNS_TTL)
-            });
-
-            return callback(
-                null,
-                formatDNSValue(value, {
-                    cached: false
-                })
-            );
-        }
-
-        resolver(6, options.host, options, (err, addresses) => {
-            if (err) {
+            // No addresses from resolve4/resolve6, try dns.lookup as fallback
+            if (ipv4Error && ipv6Error) {
+                // Both resolvers had errors
                 if (cached) {
                     dnsCache.set(options.host, {
                         value: cached.value,
@@ -201,30 +213,10 @@ module.exports.resolveHostname = (options, callback) => {
                         null,
                         formatDNSValue(cached.value, {
                             cached: true,
-                            error: err
+                            error: ipv4Error
                         })
                     );
                 }
-                return callback(err);
-            }
-
-            if (addresses && addresses.length) {
-                let value = {
-                    addresses,
-                    servername: options.servername || options.host
-                };
-
-                dnsCache.set(options.host, {
-                    value,
-                    expires: Date.now() + (options.dnsTtl || DNS_TTL)
-                });
-
-                return callback(
-                    null,
-                    formatDNSValue(value, {
-                        cached: false
-                    })
-                );
             }
 
             try {
@@ -247,19 +239,17 @@ module.exports.resolveHostname = (options, callback) => {
                         return callback(err);
                     }
 
-                    let address = addresses
-                        ? addresses
-                              .filter(addr => isFamilySupported(addr.family))
-                              .map(addr => addr.address)
-                              .shift()
-                        : false;
+                    // Get all supported addresses from dns.lookup
+                    let supportedAddresses = addresses
+                        ? addresses.filter(addr => isFamilySupported(addr.family)).map(addr => addr.address)
+                        : [];
 
-                    if (addresses && addresses.length && !address) {
+                    if (addresses && addresses.length && !supportedAddresses.length) {
                         // there are addresses but none can be used
                         console.warn(`Failed to resolve IPv${addresses[0].family} addresses with current network`);
                     }
 
-                    if (!address && cached) {
+                    if (!supportedAddresses.length && cached) {
                         // nothing was found, fallback to cached value
                         return callback(
                             null,
@@ -270,7 +260,7 @@ module.exports.resolveHostname = (options, callback) => {
                     }
 
                     let value = {
-                        addresses: address ? [address] : [options.host],
+                        addresses: supportedAddresses.length ? supportedAddresses : [options.host],
                         servername: options.servername || options.host
                     };
 
@@ -286,7 +276,7 @@ module.exports.resolveHostname = (options, callback) => {
                         })
                     );
                 });
-            } catch (_err) {
+            } catch (lookupErr) {
                 if (cached) {
                     dnsCache.set(options.host, {
                         value: cached.value,
@@ -297,11 +287,11 @@ module.exports.resolveHostname = (options, callback) => {
                         null,
                         formatDNSValue(cached.value, {
                             cached: true,
-                            error: err
+                            error: lookupErr
                         })
                     );
                 }
-                return callback(err);
+                return callback(ipv4Error || ipv6Error || lookupErr);
             }
         });
     });

package/lib/smtp-connection/http-proxy-client.js

@@ -7,6 +7,7 @@
 const net = require('net');
 const tls = require('tls');
 const urllib = require('url');
+const errors = require('../errors');
 
 /**
  * Establishes proxied connection to destinationPort
@@ -121,7 +122,9 @@ function httpProxyClient(proxyUrl, destinationPort, destinationHost, callback) {
                     } catch (_E) {
                         // ignore
                     }
-                    return callback(new Error('Invalid response from proxy' + ((match && ': ' + match[1]) || '')));
+                    let err = new Error('Invalid response from proxy' + ((match && ': ' + match[1]) || ''));
+                    err.code = errors.EPROXY;
+                    return callback(err);
                 }
 
                 socket.removeListener('error', tempSocketErr);

package/lib/smtp-connection/index.js

@@ -15,6 +15,7 @@ const CONNECTION_TIMEOUT = 2 * 60 * 1000; // how much to wait for the connection
 const SOCKET_TIMEOUT = 10 * 60 * 1000; // how much to wait for socket inactivity before disconnecting the client
 const GREETING_TIMEOUT = 30 * 1000; // how much to wait after connection is established but SMTP greeting is not receieved
 const DNS_TIMEOUT = 30 * 1000; // how much to wait for resolveHostname
+const TEARDOWN_NOOP = () => {}; // reusable no-op handler for absorbing errors during socket teardown
 
 /**
  * Generates a SMTP connection object
@@ -197,6 +198,17 @@ class SMTPConnection extends EventEmitter {
         this._onSocketClose = () => this._onClose();
         this._onSocketEnd = () => this._onEnd();
         this._onSocketTimeout = () => this._onTimeout();
+
+        /**
+         * Connection-phase error handler (supports fallback to alternative addresses)
+         */
+        this._onConnectionSocketError = err => this._onConnectionError(err, 'ESOCKET');
+
+        /**
+         * Connection attempt counter for fallback race condition protection
+         * @private
+         */
+        this._connectionAttemptId = 0;
     }
 
     /**
@@ -232,18 +244,10 @@ class SMTPConnection extends EventEmitter {
             opts.localAddress = this.options.localAddress;
         }
 
-        let setupConnectionHandlers = () => {
-            this._connectionTimeout = setTimeout(() => {
-                this._onError('Connection timeout', 'ETIMEDOUT', false, 'CONN');
-            }, this.options.connectionTimeout || CONNECTION_TIMEOUT);
-
-            this._socket.on('error', this._onSocketError);
-        };
-
         if (this.options.connection) {
             // connection is already opened
             this._socket = this.options.connection;
-            setupConnectionHandlers();
+            this._setupConnectionHandlers();
 
             if (this.secureConnection && !this.alreadySecured) {
                 setImmediate(() =>
@@ -288,7 +292,7 @@ class SMTPConnection extends EventEmitter {
                         this._socket.setKeepAlive(true);
                         this._onConnect();
                     });
-                    setupConnectionHandlers();
+                    this._setupConnectionHandlers();
                 } catch (E) {
                     return setImmediate(() => this._onError(E, 'ECONNECTION', false, 'CONN'));
                 }
@@ -327,15 +331,12 @@ class SMTPConnection extends EventEmitter {
                         opts[key] = resolved[key];
                     }
                 });
-                try {
-                    this._socket = tls.connect(opts, () => {
-                        this._socket.setKeepAlive(true);
-                        this._onConnect();
-                    });
-                    setupConnectionHandlers();
-                } catch (E) {
-                    return setImmediate(() => this._onError(E, 'ECONNECTION', false, 'CONN'));
-                }
+
+                // Store fallback addresses for retry on connection failure
+                this._fallbackAddresses = (resolved._addresses || []).filter(addr => addr !== opts.host);
+                this._connectOpts = Object.assign({}, opts);
+
+                this._connectToHost(opts, true);
             });
         } else {
             // connect using plaintext
@@ -360,19 +361,101 @@ class SMTPConnection extends EventEmitter {
                         opts[key] = resolved[key];
                     }
                 });
-                try {
-                    this._socket = net.connect(opts, () => {
-                        this._socket.setKeepAlive(true);
-                        this._onConnect();
-                    });
-                    setupConnectionHandlers();
-                } catch (E) {
-                    return setImmediate(() => this._onError(E, 'ECONNECTION', false, 'CONN'));
+
+                // Store fallback addresses for retry on connection failure
+                this._fallbackAddresses = (resolved._addresses || []).filter(addr => addr !== opts.host);
+                this._connectOpts = Object.assign({}, opts);
+
+                this._connectToHost(opts, false);
+            });
+        }
+    }
+
+    /**
+     * Attempts to connect to the specified host address
+     *
+     * @param {Object} opts Connection options
+     * @param {Boolean} secure Whether to use TLS
+     */
+    _connectToHost(opts, secure) {
+        this._connectionAttemptId++;
+        const currentAttemptId = this._connectionAttemptId;
+
+        let connectFn = secure ? tls.connect : net.connect;
+        try {
+            this._socket = connectFn(opts, () => {
+                // Ignore callback if this is a stale connection attempt
+                if (this._connectionAttemptId !== currentAttemptId) {
+                    return;
                 }
+                this._socket.setKeepAlive(true);
+                this._onConnect();
             });
+            this._setupConnectionHandlers();
+        } catch (E) {
+            return setImmediate(() => this._onError(E, 'ECONNECTION', false, 'CONN'));
         }
     }
 
+    /**
+     * Sets up connection timeout and error handlers
+     */
+    _setupConnectionHandlers() {
+        this._connectionTimeout = setTimeout(() => {
+            this._onConnectionError('Connection timeout', 'ETIMEDOUT');
+        }, this.options.connectionTimeout || CONNECTION_TIMEOUT);
+
+        this._socket.on('error', this._onConnectionSocketError);
+    }
+
+    /**
+     * Handles connection errors with fallback to alternative addresses
+     *
+     * @param {Error|String} err Error object or message
+     * @param {String} code Error code
+     */
+    _onConnectionError(err, code) {
+        clearTimeout(this._connectionTimeout);
+
+        // Check if we have fallback addresses to try
+        let canFallback = this._fallbackAddresses && this._fallbackAddresses.length && this.stage === 'init' && !this._destroyed;
+
+        if (!canFallback) {
+            // No more fallback addresses, report the error
+            this._onError(err, code, false, 'CONN');
+            return;
+        }
+
+        let nextHost = this._fallbackAddresses.shift();
+
+        this.logger.info(
+            {
+                tnx: 'network',
+                failedHost: this._connectOpts.host,
+                nextHost,
+                error: err.message || err
+            },
+            'Connection to %s failed, trying %s',
+            this._connectOpts.host,
+            nextHost
+        );
+
+        // Clean up current socket
+        if (this._socket) {
+            try {
+                this._socket.removeListener('error', this._onConnectionSocketError);
+                this._socket.destroy();
+            } catch (_E) {
+                // ignore
+            }
+            this._socket = null;
+        }
+
+        // Update host and retry
+        this._connectOpts.host = nextHost;
+        this._connectToHost(this._connectOpts, this.secureConnection);
+    }
+
     /**
      * Sends QUIT
      */
@@ -414,6 +497,18 @@ class SMTPConnection extends EventEmitter {
 
         if (socket && !socket.destroyed) {
             try {
+                // Clear socket timeout to prevent timer leaks
+                socket.setTimeout(0);
+                // Remove all listeners to allow proper garbage collection
+                socket.removeListener('data', this._onSocketData);
+                socket.removeListener('timeout', this._onSocketTimeout);
+                socket.removeListener('close', this._onSocketClose);
+                socket.removeListener('end', this._onSocketEnd);
+                socket.removeListener('error', this._onSocketError);
+                socket.removeListener('error', this._onConnectionSocketError);
+                // Absorb errors that may fire during socket teardown (e.g. server
+                // sending cleartext after TLS shutdown triggers ERR_SSL_BAD_RECORD_TYPE)
+                socket.on('error', TEARDOWN_NOOP);
                 socket[closeMethod]();
             } catch (_E) {
                 // just ignore
@@ -715,7 +810,10 @@ class SMTPConnection extends EventEmitter {
         this._socket.removeListener('timeout', this._onSocketTimeout);
         this._socket.removeListener('close', this._onSocketClose);
         this._socket.removeListener('end', this._onSocketEnd);
+        // Switch from connection-phase error handler to normal error handler
+        this._socket.removeListener('error', this._onConnectionSocketError);
 
+        this._socket.on('error', this._onSocketError);
         this._socket.on('data', this._onSocketData);
         this._socket.once('close', this._onSocketClose);
         this._socket.once('end', this._onSocketEnd);
@@ -941,8 +1039,10 @@ class SMTPConnection extends EventEmitter {
                 this.upgrading = false;
                 this._socket.on('data', this._onSocketData);
 
+                // Remove all listeners from the plain socket to allow proper garbage collection
                 socketPlain.removeListener('close', this._onSocketClose);
                 socketPlain.removeListener('end', this._onSocketEnd);
+                socketPlain.removeListener('error', this._onSocketError);
 
                 return callback(null, true);
             });

package/lib/smtp-pool/index.js

@@ -5,6 +5,7 @@ const PoolResource = require('./pool-resource');
 const SMTPConnection = require('../smtp-connection');
 const wellKnown = require('../well-known');
 const shared = require('../shared');
+const errors = require('../errors');
 const packageData = require('../../package.json');
 
 /**
@@ -633,7 +634,7 @@ class SMTPPool extends EventEmitter {
                     });
                 } else if (!auth && connection.allowsAuth && options.forceAuth) {
                     let err = new Error('Authentication info was not provided');
-                    err.code = 'NoAuth';
+                    err.code = errors.ENOAUTH;
 
                     returned = true;
                     connection.close();

package/lib/smtp-pool/pool-resource.js

@@ -3,6 +3,7 @@
 const SMTPConnection = require('../smtp-connection');
 const assign = require('../shared').assign;
 const XOAuth2 = require('../xoauth2');
+const errors = require('../errors');
 const EventEmitter = require('events');
 
 /**
@@ -121,7 +122,7 @@ class PoolResource extends EventEmitter {
                     let err = new Error('Unexpected socket close');
                     if (this.connection && this.connection._socket && this.connection._socket.upgrading) {
                         // starttls connection errors
-                        err.code = 'ETLS';
+                        err.code = errors.ETLS;
                     }
                     callback(err);
                 }, 1000);
@@ -226,7 +227,7 @@ class PoolResource extends EventEmitter {
                 let err;
                 if (this.messages >= this.options.maxMessages) {
                     err = new Error('Resource exhausted');
-                    err.code = 'EMAXLIMIT';
+                    err.code = errors.EMAXLIMIT;
                     this.connection.close();
                     this.emit('error', err);
                 } else {

package/lib/smtp-transport/index.js

@@ -5,6 +5,7 @@ const SMTPConnection = require('../smtp-connection');
 const wellKnown = require('../well-known');
 const shared = require('../shared');
 const XOAuth2 = require('../xoauth2');
+const errors = require('../errors');
 const packageData = require('../../package.json');
 
 /**
@@ -190,7 +191,7 @@ class SMTPTransport extends EventEmitter {
                     let err = new Error('Unexpected socket close');
                     if (connection && connection._socket && connection._socket.upgrading) {
                         // starttls connection errors
-                        err.code = 'ETLS';
+                        err.code = errors.ETLS;
                     }
                     callback(err);
                 }, 1000);
@@ -392,7 +393,7 @@ class SMTPTransport extends EventEmitter {
                     });
                 } else if (!authData && connection.allowsAuth && options.forceAuth) {
                     let err = new Error('Authentication info was not provided');
-                    err.code = 'NoAuth';
+                    err.code = errors.ENOAUTH;
 
                     returned = true;
                     connection.close();

package/lib/well-known/services.json

@@ -147,6 +147,14 @@
         "secure": true
     },
 
+    "GmailWorkspace": {
+        "description": "Gmail Workspace",
+        "aliases": ["Google Workspace Mail"],
+        "host": "smtp-relay.gmail.com",
+        "port": 465,
+        "secure": true
+    },
+
     "GMX": {
         "description": "GMX Mail",
         "domains": ["gmx.com", "gmx.net", "gmx.de"],

package/lib/xoauth2/index.js

@@ -4,6 +4,7 @@ const Stream = require('stream').Stream;
 const nmfetch = require('../fetch');
 const crypto = require('crypto');
 const shared = require('../shared');
+const errors = require('../errors');
 
 /**
  * XOAUTH2 access_token generator for Gmail.
@@ -41,7 +42,9 @@ class XOAuth2 extends Stream {
 
         if (options && options.serviceClient) {
             if (!options.privateKey || !options.user) {
-                setImmediate(() => this.emit('error', new Error('Options "privateKey" and "user" are required for service account!')));
+                let err = new Error('Options "privateKey" and "user" are required for service account!');
+                err.code = errors.EOAUTH2;
+                setImmediate(() => this.emit('error', err));
                 return;
             }
 
@@ -120,7 +123,9 @@ class XOAuth2 extends Stream {
                 'Cannot renew access token for %s: No refresh mechanism available',
                 this.options.user
             );
-            return callback(new Error("Can't create new access token for user"));
+            let err = new Error("Can't create new access token for user");
+            err.code = errors.EOAUTH2;
+            return callback(err);
         }
 
         // If renewal already in progress, queue this request instead of starting another
@@ -218,7 +223,9 @@ class XOAuth2 extends Stream {
             try {
                 token = this.jwtSignRS256(tokenData);
             } catch (_err) {
-                return callback(new Error("Can't generate token. Check your auth options"));
+                let err = new Error("Can't generate token. Check your auth options");
+                err.code = errors.EOAUTH2;
+                return callback(err);
             }
 
             urlOptions = {
@@ -232,7 +239,9 @@ class XOAuth2 extends Stream {
             };
         } else {
             if (!this.options.refreshToken) {
-                return callback(new Error("Can't create new access token for user"));
+                let err = new Error("Can't create new access token for user");
+                err.code = errors.EOAUTH2;
+                return callback(err);
             }
 
             // web app - https://developers.google.com/identity/protocols/OAuth2WebServer
@@ -289,7 +298,9 @@ class XOAuth2 extends Stream {
                     'Response: %s',
                     (body || '').toString()
                 );
-                return callback(new Error('Invalid authentication response'));
+                let err = new Error('Invalid authentication response');
+                err.code = errors.EOAUTH2;
+                return callback(err);
             }
 
             let logData = {};
@@ -320,7 +331,9 @@ class XOAuth2 extends Stream {
                 if (data.error_uri) {
                     errorMessage += ' (' + data.error_uri + ')';
                 }
-                return callback(new Error(errorMessage));
+                let err = new Error(errorMessage);
+                err.code = errors.EOAUTH2;
+                return callback(err);
             }
 
             if (data.access_token) {
@@ -328,7 +341,9 @@ class XOAuth2 extends Stream {
                 return callback(null, this.accessToken);
             }
 
-            return callback(new Error('No access token'));
+            let err = new Error('No access token');
+            err.code = errors.EOAUTH2;
+            return callback(err);
         });
     }
 

package/package.json

@@ -1,6 +1,6 @@
 {
     "name": "nodemailer",
-    "version": "7.0.13",
+    "version": "8.0.1",
     "description": "Easy as cake e-mail sending from your Node.js applications",
     "main": "lib/nodemailer.js",
     "scripts": {
@@ -26,12 +26,12 @@
     },
     "homepage": "https://nodemailer.com/",
     "devDependencies": {
-        "@aws-sdk/client-sesv2": "3.975.0",
+        "@aws-sdk/client-sesv2": "3.985.0",
         "bunyan": "1.8.15",
         "c8": "10.1.3",
-        "eslint": "9.39.2",
+        "eslint": "10.0.0",
         "eslint-config-prettier": "10.1.8",
-        "globals": "17.1.0",
+        "globals": "17.3.0",
         "libbase64": "1.3.0",
         "libmime": "5.3.7",
         "libqp": "2.1.1",
@@ -39,7 +39,7 @@
         "prettier": "3.8.1",
         "proxy": "1.0.2",
         "proxy-test-server": "1.0.0",
-        "smtp-server": "3.18.0"
+        "smtp-server": "3.18.1"
     },
     "engines": {
         "node": ">=6.0.0"