@mavogel/awscdk-rootmail 0.1.7 → 0.1.9

package/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
- *  * **requireTLS** - forces the client to use STARTTLS
+ *  * **ignoreTLS** - ignore server support for STARTTLS (has no effect when requireTLS is set)
+ *  * **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
@@ -414,14 +433,21 @@ class SMTPConnection extends EventEmitter {
         this._auth = authData || {};
         // Select SASL authentication method
         this._authMethod = (this._auth.method || '').toString().trim().toUpperCase() || false;
+        // XOAUTH2 needs a token generator or a custom handler, without either the method
+        // can not be run even when it is the only one the server advertised
+        const canUseXOAuth2 = !!this._auth.oauth2 || this.customAuth.has('XOAUTH2');
         if (!this._authMethod && this._auth.oauth2 && !this._auth.credentials) {
             this._authMethod = 'XOAUTH2';
         }
         else if (!this._authMethod || (this._authMethod === 'XOAUTH2' && !this._auth.oauth2)) {
-            // use first supported
-            this._authMethod = (this._supportedAuth[0] || 'PLAIN').toUpperCase().trim();
-        }
-        if (this._authMethod !== 'XOAUTH2' && (!this._auth.credentials || !this._auth.credentials.user || !this._auth.credentials.pass)) {
+            // use the first supported method that can be run
+            const supported = this._supportedAuth.find(method => method !== 'XOAUTH2' || canUseXOAuth2);
+            this._authMethod = (supported || 'PLAIN').toUpperCase().trim();
+        }
+        // a token login needs no credentials, every other method and every custom handler
+        // gets them filled in from the user and pass values
+        if ((this._authMethod !== 'XOAUTH2' || this.customAuth.has('XOAUTH2')) &&
+            (!this._auth.credentials || !this._auth.credentials.user || !this._auth.credentials.pass)) {
             if ((this._auth.user && this._auth.pass) || this.customAuth.has(this._authMethod)) {
                 this._auth.credentials = {
                     user: this._auth.user,
@@ -458,42 +484,45 @@ class SMTPConnection extends EventEmitter {
                 returned = true;
                 callback(this._formatError(err, 'EAUTH', lastResponse, 'AUTH ' + this._authMethod));
             };
+            // one implementation serves both sendCommand overloads, the promise is returned
+            // exactly when no callback was given
+            const sendCommand = (cmd, done) => {
+                let promise;
+                if (!done) {
+                    promise = new Promise((resolve, reject) => {
+                        done = shared.callbackPromise(resolve, reject);
+                    });
+                }
+                this._responseActions.push(str => {
+                    lastResponse = str;
+                    let codes = str.match(/^(\d+)(?:\s(\d+\.\d+\.\d+))?\s/);
+                    let data = {
+                        command: cmd,
+                        response: str
+                    };
+                    if (codes) {
+                        data.status = Number(codes[1]) || 0;
+                        if (codes[2]) {
+                            data.code = codes[2];
+                        }
+                        data.text = str.substr(codes[0].length);
+                    }
+                    else {
+                        data.text = str;
+                        data.status = 0; // just in case we need to perform numeric comparisons
+                    }
+                    done(null, data);
+                });
+                setImmediate(() => this._sendCommand(cmd));
+                return promise;
+            };
             const handlerResponse = handler({
                 auth: this._auth,
                 method: this._authMethod,
                 extensions: [].concat(this._supportedExtensions),
                 authMethods: [].concat(this._supportedAuth),
                 maxAllowedSize: this._maxAllowedSize || false,
-                sendCommand: (cmd, done) => {
-                    let promise;
-                    if (!done) {
-                        promise = new Promise((resolve, reject) => {
-                            done = shared.callbackPromise(resolve, reject);
-                        });
-                    }
-                    this._responseActions.push(str => {
-                        lastResponse = str;
-                        let codes = str.match(/^(\d+)(?:\s(\d+\.\d+\.\d+))?\s/);
-                        let data = {
-                            command: cmd,
-                            response: str
-                        };
-                        if (codes) {
-                            data.status = Number(codes[1]) || 0;
-                            if (codes[2]) {
-                                data.code = codes[2];
-                            }
-                            data.text = str.substr(codes[0].length);
-                        }
-                        else {
-                            data.text = str;
-                            data.status = 0; // just in case we need to perform numeric comparisons
-                        }
-                        done(null, data);
-                    });
-                    setImmediate(() => this._sendCommand(cmd));
-                    return promise;
-                },
+                sendCommand: sendCommand,
                 resolve,
                 reject
             });
@@ -547,35 +576,46 @@ class SMTPConnection extends EventEmitter {
      *
      * @param envelope Envelope object, {from: addr, to: [addr]}
      * @param message String, Buffer or a Stream
-     * @param callback Callback to return once sending is completed
+     * @param done Callback to return once sending is completed
      */
     send(envelope, message, done) {
+        // ensure that the callback is only called once. The public callback type has a
+        // required result, the error paths hand over the error alone
+        let returned = false;
+        const callback = (err, info) => {
+            if (returned) {
+                return;
+            }
+            returned = true;
+            if (this._pendingSend && this._pendingSend.callback === callback) {
+                this._pendingSend = false;
+            }
+            done(err, info);
+        };
         if (!message) {
-            return done(this._formatError('Empty message', 'EMESSAGE', false, 'API'));
+            return callback(this._formatError('Empty message', 'EMESSAGE', false, 'API'));
         }
         const isDestroyedMessage = this._isDestroyedMessage('send message');
         if (isDestroyedMessage) {
-            return done(this._formatError(isDestroyedMessage, 'ECONNECTION', false, 'API'));
+            return callback(this._formatError(isDestroyedMessage, 'ECONNECTION', false, 'API'));
         }
         // reject larger messages than allowed
         if (this._maxAllowedSize && envelope.size > this._maxAllowedSize) {
             setImmediate(() => {
-                done(this._formatError('Message size larger than allowed ' + this._maxAllowedSize, 'EMESSAGE', false, 'MAIL FROM'));
+                callback(this._formatError('Message size larger than allowed ' + this._maxAllowedSize, 'EMESSAGE', false, 'MAIL FROM'));
             });
             return;
         }
-        // ensure that callback is only called once
-        let returned = false;
-        const callback = function (...args) {
-            if (returned) {
-                return;
-            }
-            returned = true;
-            done(...args);
+        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) {
@@ -595,11 +635,13 @@ class SMTPConnection extends EventEmitter {
                 if (err) {
                     return callback(err);
                 }
-                info.envelopeTime = envelopeTime - startTime;
-                info.messageTime = Date.now() - envelopeTime;
-                info.messageSize = stream.outByteCount;
-                info.response = str;
-                return callback(null, info);
+                // the envelope info becomes the send result once the timings are on it
+                const result = info;
+                result.envelopeTime = envelopeTime - startTime;
+                result.messageTime = Date.now() - envelopeTime;
+                result.messageSize = stream.outByteCount;
+                result.response = str;
+                return callback(null, result);
             });
             if (typeof message.pipe === 'function') {
                 message.pipe(stream);
@@ -747,6 +789,8 @@ class SMTPConnection extends EventEmitter {
      * @event
      * @param err Error object
      * @param type Error name
+     * @param data Server response that triggered the error, false if there is none
+     * @param command SMTP command that was in flight
      * @internal
      */
     _onError(err, type, data, command) {
@@ -766,8 +810,14 @@ 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) {
@@ -813,14 +863,25 @@ 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');
-        }
-        else if (![this._actionGreeting, this.close].includes(this._responseActions[0]) && !this._destroyed) {
-            return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', serverResponse, 'CONN');
+            return this._onError(new Error('Connection closed unexpectedly'), 'ETLS', failureResponse, 'CONN');
+        }
+        if (!failureResponse && this._responseActions[0] === this._actionGreeting && this._connectCallback && !this._destroyed) {
+            // 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)) {
-            return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', serverResponse, 'CONN');
+        if (failureResponse || (this._responseActions[0] !== this.close && !this._destroyed)) {
+            return this._onError(new Error('Connection closed unexpectedly'), 'ECONNECTION', failureResponse, 'CONN');
         }
         this._destroy();
     }
@@ -998,6 +1059,7 @@ class SMTPConnection extends EventEmitter {
      *        {from:'...', to:['...']}
      *        or
      *        {from:{address:'...',name:'...'}, to:[address:'...',name:'...']}
+     * @param callback Callback to run once the envelope is processed
      * @internal
      */
     _setEnvelope(envelope, callback) {
@@ -1297,21 +1359,25 @@ class SMTPConnection extends EventEmitter {
         if (/[ -]AUTH\b/i.test(str)) {
             this.allowsAuth = true;
         }
-        // Detect if the server supports PLAIN auth
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)PLAIN/i.test(str)) {
-            this._supportedAuth.push('PLAIN');
-        }
-        // Detect if the server supports LOGIN auth
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)LOGIN/i.test(str)) {
-            this._supportedAuth.push('LOGIN');
-        }
-        // 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 the advertised SASL mechanisms. The list is split into whole tokens rather
+        // than searched for each name with a pattern: the patterns this replaced let two
+        // 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 XOAUTH2 auth
-        if (/[ -]AUTH(?:(\s+|=)[^\n]*\s+|\s+|=)XOAUTH2/i.test(str)) {
-            this._supportedAuth.push('XOAUTH2');
+        // listed in order of preference, the first one the credentials allow is used
+        for (const mechanism of ['PLAIN', 'LOGIN', 'CRAM-MD5', 'XOAUTH2']) {
+            if (authMechanisms.has(mechanism)) {
+                this._supportedAuth.push(mechanism);
+            }
         }
         // Detect if the server supports SIZE extensions (and the max allowed size)
         if ((match = str.match(/[ -]SIZE(?:[ \t]+(\d+))?/im))) {
@@ -1388,6 +1454,7 @@ class SMTPConnection extends EventEmitter {
      * hosts invalidly use a longer message than VXNlcm5hbWU6
      *
      * @param str Message from the server
+     * @param callback Callback to run once the authentication sequence completes
      * @internal
      */
     _actionAUTH_LOGIN_USER(str, callback) {
@@ -1409,6 +1476,7 @@ class SMTPConnection extends EventEmitter {
      * base64 encoded again.
      *
      * @param str Message from the server
+     * @param callback Callback to run once the authentication sequence completes
      * @internal
      */
     _actionAUTH_CRAM_MD5(str, callback) {
@@ -1433,6 +1501,7 @@ class SMTPConnection extends EventEmitter {
      * the user can be considered logged in. Start waiting for a message to send
      *
      * @param str Message from the server
+     * @param callback Callback to run once the authentication sequence completes
      * @internal
      */
     _actionAUTH_CRAM_MD5_PASS(str, callback) {
@@ -1454,6 +1523,7 @@ class SMTPConnection extends EventEmitter {
      * response needs to be base64 encoded password.
      *
      * @param str Message from the server
+     * @param callback Callback to run once the authentication sequence completes
      * @internal
      */
     _actionAUTH_LOGIN_PASS(str, callback) {
@@ -1473,6 +1543,8 @@ class SMTPConnection extends EventEmitter {
      * the user can be considered logged in. Start waiting for a message to send
      *
      * @param str Message from the server
+     * @param isRetry True if this is a retry after a failed login, or the callback itself
+     * @param [callback] Callback to run once the authentication sequence completes
      * @internal
      */
     _actionAUTHComplete(str, isRetry, callback) {
@@ -1515,6 +1587,7 @@ class SMTPConnection extends EventEmitter {
      * Handle response for a MAIL FROM: command
      *
      * @param str Message from the server
+     * @param callback Callback to run once the envelope is processed
      * @internal
      */
     _actionMAIL(str, callback) {
@@ -1543,6 +1616,7 @@ class SMTPConnection extends EventEmitter {
      * Handle response for a RCPT TO: command
      *
      * @param str Message from the server
+     * @param callback Callback to run once the envelope is processed
      * @internal
      */
     _actionRCPT(str, callback) {
@@ -1571,7 +1645,11 @@ 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);
@@ -1590,6 +1668,7 @@ class SMTPConnection extends EventEmitter {
      * Handle response for a DATA command
      *
      * @param str Message from the server
+     * @param callback Callback to run once the envelope is processed
      * @internal
      */
     _actionDATA(str, callback) {
@@ -1616,6 +1695,7 @@ class SMTPConnection extends EventEmitter {
      * We expect a single response that defines if the sending succeeded or failed
      *
      * @param str Message from the server
+     * @param callback Callback to run with the final send result
      * @internal
      */
     _actionSMTPStream(str, callback) {
@@ -1632,6 +1712,7 @@ class SMTPConnection extends EventEmitter {
      * @param recipient The recipient this response applies to
      * @param final Is this the final recipient?
      * @param str Message from the server
+     * @param callback Callback to run with the final send result
      * @internal
      */
     _actionLMTPStream(recipient, final, str, callback) {

package/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
@@ -80,7 +81,7 @@ declare class SMTPPool extends EventEmitter {
     /**
      * The Mail instance using this transport, assigned by Mail
      */
-    mailer?: Mail<SMTPPoolSentMessageInfo> | undefined;
+    mailer?: Mail<SMTPPoolSentMessageInfo, SMTPPoolOptions> | undefined;
     constructor(options?: SMTPPoolOptions | string);
     /**
      * Placeholder function for creating proxy sockets. This method immediatelly returns
@@ -96,7 +97,7 @@ declare class SMTPPool extends EventEmitter {
      * @param mail Mail object
      * @param callback Callback function
      */
-    send(mail: MailMessage, callback: SMTPPoolSendCallback): boolean;
+    send(mail: MailMessage<SMTPPoolSentMessageInfo>, callback: SMTPPoolSendCallback): boolean;
     /**
      * Closes all connections in the pool. If there is a message being sent, the connection
      * is closed later
@@ -109,9 +110,14 @@ declare class SMTPPool extends EventEmitter {
     /**
      * Verifies SMTP configuration
      *
-     * @param callback Callback function
+     * @returns Promise that resolves to true if the configuration is usable
      */
     verify(): Promise<true>;
+    /**
+     * Verifies SMTP configuration
+     *
+     * @param callback Callback function
+     */
     verify(callback: VerifyCallback): void;
 }
 /**
@@ -122,4 +128,6 @@ declare namespace SMTPPool {
     type MailOptions = SendMailOptions;
     type SentMessageInfo = SMTPPoolSentMessageInfo;
 }
+/** The same aliases as module level exports, for `import * as SMTPPool` and `import SMTPPool = require()` */
+export type { SMTPPoolOptions as Options, SendMailOptions as MailOptions, SMTPPoolSentMessageInfo as SentMessageInfo };
 export default SMTPPool;

package/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
@@ -424,10 +445,12 @@ class SMTPPool extends EventEmitter {
                 callback = shared.callbackPromise(resolve, reject);
             });
         }
+        // the error paths hand over the error alone
+        const done = callback;
         const auth = new PoolResource(this).auth;
         this.getSocket(this.options, (err, socketOptions) => {
             if (err) {
-                return callback(err);
+                return done(err);
             }
             let options = this.options;
             if (socketOptions && socketOptions.connection) {
@@ -449,14 +472,14 @@ class SMTPPool extends EventEmitter {
                 }
                 returned = true;
                 connection.close();
-                return callback(err);
+                return done(err);
             });
             connection.once('end', () => {
                 if (returned) {
                     return;
                 }
                 returned = true;
-                return callback(new Error('Connection closed'));
+                return done(new Error('Connection closed'));
             });
             const finalize = () => {
                 if (returned) {
@@ -464,12 +487,17 @@ class SMTPPool extends EventEmitter {
                 }
                 returned = true;
                 connection.quit();
-                return callback(null, true);
+                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) {
@@ -478,7 +506,7 @@ class SMTPPool extends EventEmitter {
                         if (err) {
                             returned = true;
                             connection.close();
-                            return callback(err);
+                            return done(err);
                         }
                         finalize();
                     });
@@ -488,7 +516,7 @@ class SMTPPool extends EventEmitter {
                     err.code = errors.ENOAUTH;
                     returned = true;
                     connection.close();
-                    return callback(err);
+                    return done(err);
                 }
                 else {
                     finalize();