nodemailer 10.1.7 → 10.2.1

package/dist/esm/mime-funcs/index.js

@@ -365,6 +365,26 @@ export function buildHeaderParam(key, data, maxLength) {
  * goes in. Whitespace used to come off it only because the value was trimmed first.
  */
 const TOKEN = /^[^\x00-\x20\x7f()<>@,;:\\"/[\]?=]+$/;
+/**
+ * Offset of the ')' that closes the RFC 822 comment opening at `start`, or -1 when the
+ * comment never closes. Comments nest, and a backslash escapes the character after it
+ */
+function _findCommentEnd(str, start) {
+    let depth = 0;
+    for (let i = start, len = str.length; i < len; i++) {
+        const c = str.charAt(i);
+        if (c === '\\') {
+            i++;
+        }
+        else if (c === '(') {
+            depth++;
+        }
+        else if (c === ')' && --depth === 0) {
+            return i;
+        }
+    }
+    return -1;
+}
 /**
  * Whether a string can be a header parameter name.
  *
@@ -391,13 +411,16 @@ function _isParamName(name) {
  *   }
  *
  * @param str Header value
+ * @param options Options, see ParseHeaderValueOptions
  * @return Header value as a parsed structure
  */
-export function parseHeaderValue(str) {
+export function parseHeaderValue(str, options) {
     const response = {
         value: '',
         params: {}
     };
+    // Cleared again by an unclosed '(', see the loop
+    let stripComments = !!options?.stripComments;
     // A duplicated parameter resolves to its first occurrence, the way a duplicated header
     // does. Letting the last one win disagrees with the receivers that take the first, and
     // the two readings of 'boundary="b"; boundary="c"' name different delimiters. The
@@ -459,6 +482,25 @@ export function parseHeaderValue(str) {
     };
     for (let i = 0, len = str.length; i < len; i++) {
         chr = str.charAt(i);
+        // With stripComments, an RFC 822 comment stands anywhere outside a quoted string but
+        // right behind a token it would continue, see ParseHeaderValueOptions. In the value
+        // of a parameter, no pending whitespace means the last significant character was the
+        // '=' or a character of the token
+        if (stripComments && chr === '(' && !quote && !quoteClosed && !(stage === 'value' && key !== false && !pendingSpace)) {
+            let end = _findCommentEnd(str, i);
+            if (end < 0 && str.indexOf(';', i) < 0) {
+                // a comment that never closes runs to the end of the value, unless a
+                // parameter follows it, which is content then and survives
+                end = len - 1;
+            }
+            if (end >= 0) {
+                i = end;
+                continue;
+            }
+            // looking for a closing ')' again would scan a run of unclosed '(' to its end
+            // once for each of them
+            stripComments = false;
+        }
         if (stage === 'key') {
             if (chr === '=') {
                 key = takeValue().trim();

package/dist/esm/mime-funcs/mime-types.js

@@ -1097,10 +1097,7 @@ const extensions = new Map([
     ['bdm', 'application/vnd.syncml.dm+wbxml'],
     ['bed', 'application/vnd.realvnc.bed'],
     ['bh2', 'application/vnd.fujitsu.oasysprs'],
-    [
-        'bin',
-        ['application/octet-stream', 'application/mac-binary', 'application/macbinary', 'application/x-macbinary', 'application/x-binary']
-    ],
+    ['bin', ['application/octet-stream', 'application/mac-binary', 'application/macbinary', 'application/x-macbinary', 'application/x-binary']],
     ['bm', 'image/bmp'],
     ['bmi', 'application/vnd.bmi'],
     ['bmp', ['image/bmp', 'image/x-windows-bmp']],
@@ -1145,10 +1142,7 @@ const extensions = new Map([
     ['cii', 'application/vnd.anser-web-certificate-issue-initiation'],
     ['cil', 'application/vnd.ms-artgalry'],
     ['cla', 'application/vnd.claymore'],
-    [
-        'class',
-        ['application/octet-stream', 'application/java', 'application/java-byte-code', 'application/java-vm', 'application/x-java-class']
-    ],
+    ['class', ['application/octet-stream', 'application/java', 'application/java-byte-code', 'application/java-vm', 'application/x-java-class']],
     ['clkk', 'application/vnd.crick.clicker.keyboard'],
     ['clkp', 'application/vnd.crick.clicker.palette'],
     ['clkt', 'application/vnd.crick.clicker.template'],
@@ -1753,10 +1747,7 @@ const extensions = new Map([
     ['sbml', 'application/sbml+xml'],
     ['sc', 'application/vnd.ibm.secure-container'],
     ['scd', 'application/x-msschedule'],
-    [
-        'scm',
-        ['application/vnd.lotus-screencam', 'video/x-scm', 'text/x-script.guile', 'application/x-lotusscreencam', 'text/x-script.scheme']
-    ],
+    ['scm', ['application/vnd.lotus-screencam', 'video/x-scm', 'text/x-script.guile', 'application/x-lotusscreencam', 'text/x-script.scheme']],
     ['scq', 'application/scvp-cv-request'],
     ['scs', 'application/scvp-cv-response'],
     ['sct', 'text/scriptlet'],

package/dist/esm/mime-node/index.d.ts

@@ -58,6 +58,13 @@ export interface MimeNodePreparedHeaderValue {
  * objects (for the address headers), a prepared value object, or a list of these
  */
 export type MimeNodeHeaderValue = string | number | boolean | Date | MimeNodeAddress | MimeNodePreparedHeaderValue | MimeNodeHeaderValue[] | null | undefined;
+/**
+ * Options for the static MimeNode.encodeHeaderValue
+ */
+export interface MimeNodeHeaderEncodingOptions {
+    /** Either 'Q' (the default) or 'B' */
+    textEncoding?: string | undefined;
+}
 /**
  * A single header, the shape the headers are stored in and one of the list forms
  * setHeader and addHeader accept
@@ -319,6 +326,31 @@ declare class MimeNode {
      * @param raw Raw MIME contents
      */
     setRaw(raw: MimeNodeContent): this;
+    /**
+     * Encodes a header value the way this node encodes it in the generated message:
+     * address headers are punycoded and mime encoded, message id headers get their
+     * angle brackets, a Date object is formatted and any other value is mime encoded
+     * when it holds non-ascii or control characters (using the node's `textEncoding`).
+     *
+     * The result is a single unfolded line without the key. Fold it before writing it
+     * into a message, `key + ': ' + value` folded at 76 characters is what the node does.
+     *
+     * @param key Header key, case insensitive
+     * @param value Header value
+     * @returns Encoded header value
+     */
+    encodeHeaderValue(key: string, value: MimeNodeHeaderValue): string;
+    /**
+     * Encodes a header value without a node at hand. Same as the instance method of a
+     * node created with the given options.
+     *
+     * @param key Header key, case insensitive
+     * @param value Header value
+     * @param [options] Encoding options
+     * @param [options.textEncoding] either 'Q' (the default) or 'B'
+     * @returns Encoded header value
+     */
+    static encodeHeaderValue(key: string, value: MimeNodeHeaderValue, options?: MimeNodeHeaderEncodingOptions): string;
 }
 /**
  * Type aliases in the layout of @types/nodemailer, so `MimeNode.Options` style references keep working
@@ -327,7 +359,8 @@ declare namespace MimeNode {
     type Options = MimeNodeOptions;
     type Addresses = MimeNodeAddresses;
     type Envelope = MimeNodeEnvelope;
+    type HeaderEncodingOptions = MimeNodeHeaderEncodingOptions;
 }
 /** The same aliases as module level exports, for `import * as MimeNode` and `import MimeNode = require()` */
-export type { MimeNodeOptions as Options, MimeNodeAddresses as Addresses, MimeNodeEnvelope as Envelope };
+export type { MimeNodeOptions as Options, MimeNodeAddresses as Addresses, MimeNodeEnvelope as Envelope, MimeNodeHeaderEncodingOptions as HeaderEncodingOptions };
 export default MimeNode;

package/dist/esm/mime-node/index.js

@@ -117,9 +117,7 @@ function exceedsDomainLimits(domain) {
  */
 function normalizeDomain(domain, toUnicode) {
     // domainToASCII and domainToUnicode landed in Node 7, the bundled codec covers Node 6
-    if (typeof urlModule.domainToASCII === 'function' &&
-        typeof urlModule.domainToUnicode === 'function' &&
-        !URL_PARSER_UNSAFE.test(domain)) {
+    if (typeof urlModule.domainToASCII === 'function' && typeof urlModule.domainToUnicode === 'function' && !URL_PARSER_UNSAFE.test(domain)) {
         // The U-label form is decoded from the A-label form rather than from the input:
         // Deno's domainToASCII returns an empty string for a label it cannot decode, while
         // its domainToUnicode returns the label with U+FFFD in place of the bad part
@@ -618,23 +616,24 @@ class MimeNode {
                 return;
             }
             switch (header.key) {
+                // The comments of a MIME header are not part of its value and are dropped, so a
+                // caller supplied 'boundary=b (comment)' is the boundary b it names, and the
+                // header goes out without the comment
                 case 'Content-Disposition':
-                    structured = mimeFuncs.parseHeaderValue(value);
+                    structured = mimeFuncs.parseHeaderValue(value, { stripComments: true });
                     if (this.filename) {
                         structured.params.filename = this.filename;
                     }
                     value = mimeFuncs.buildHeaderValue(structured);
                     break;
                 case 'Content-Type':
-                    structured = mimeFuncs.parseHeaderValue(value);
+                    structured = mimeFuncs.parseHeaderValue(value, { stripComments: true });
                     // the type token decides multipart and charset below, so clean it before
                     // those run and not just on the way out, otherwise a control char makes
                     // the checks miss and the header ends up claiming a type it is not set up for
                     structured.value = (structured.value || '').toString().replace(/[\x00-\x1f\x7f]/g, '');
                     this._handleContentType(structured);
-                    if (structured.value.match(/^text\/plain\b/) &&
-                        typeof this.content === 'string' &&
-                        /[\u0080-\uFFFF]/.test(this.content)) {
+                    if (structured.value.match(/^text\/plain\b/) && typeof this.content === 'string' && /[\u0080-\uFFFF]/.test(this.content)) {
                         structured.params.charset = 'utf-8';
                     }
                     if (this.filename) {
@@ -675,7 +674,7 @@ class MimeNode {
                     }
                     break;
             }
-            value = this._encodeHeaderValue(key, value);
+            value = this.encodeHeaderValue(key, value);
             // skip empty lines
             if (!(value || '').toString().trim()) {
                 return;
@@ -1293,8 +1292,7 @@ class MimeNode {
             // where it came from. MimeNode is exported and subclassable, so the generator is
             // not necessarily the one below. Stripping twice costs nothing, it is idempotent.
             const declared = _stripBoundaryControls(structured.params.boundary || this.boundary || '');
-            this.boundary = structured.params.boundary =
-                declared || _stripBoundaryControls(this._generateBoundary());
+            this.boundary = structured.params.boundary = declared || _stripBoundaryControls(this._generateBoundary());
         }
         else {
             this.boundary = false;
@@ -1312,13 +1310,19 @@ class MimeNode {
         return _stripBoundaryControls(this.rootNode.boundaryPrefix + '-' + this.rootNode.baseBoundary) + '-Part_' + this._nodeId;
     }
     /**
-     * Encodes a header value for use in the generated rfc2822 email.
+     * Encodes a header value the way this node encodes it in the generated message:
+     * address headers are punycoded and mime encoded, message id headers get their
+     * angle brackets, a Date object is formatted and any other value is mime encoded
+     * when it holds non-ascii or control characters (using the node's `textEncoding`).
      *
-     * @param key Header key
+     * The result is a single unfolded line without the key. Fold it before writing it
+     * into a message, `key + ': ' + value` folded at 76 characters is what the node does.
+     *
+     * @param key Header key, case insensitive
      * @param value Header value
-     * @internal
+     * @returns Encoded header value
      */
-    _encodeHeaderValue(key, value) {
+    encodeHeaderValue(key, value) {
         key = this._normalizeHeaderKey(key);
         switch (key) {
             // Structured headers
@@ -1383,6 +1387,27 @@ class MimeNode {
                 return this._encodeHeaderText(value);
         }
     }
+    /**
+     * Encodes a header value without a node at hand. Same as the instance method of a
+     * node created with the given options.
+     *
+     * @param key Header key, case insensitive
+     * @param value Header value
+     * @param [options] Encoding options
+     * @param [options.textEncoding] either 'Q' (the default) or 'B'
+     * @returns Encoded header value
+     */
+    static encodeHeaderValue(key, value, options) {
+        return new MimeNode(false, { textEncoding: options?.textEncoding }).encodeHeaderValue(key, value);
+    }
+    /**
+     * Alias of encodeHeaderValue, kept for callers that used the method before it was public
+     *
+     * @internal
+     */
+    _encodeHeaderValue(key, value) {
+        return this.encodeHeaderValue(key, value);
+    }
     /**
      * Rebuilds address object using punycode and other adjustments
      *

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

@@ -1,3 +1,3 @@
 export declare const name = "nodemailer";
-export declare const version = "10.1.7";
+export declare const version = "10.2.1";
 export declare const homepage = "https://nodemailer.com/";

package/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 = '10.1.7';
+export const version = '10.2.1';
 export const homepage = 'https://nodemailer.com/';

package/dist/esm/qp/index.js

@@ -45,15 +45,9 @@ function encodeBytes(buffer, next, binary, previous) {
     for (let i = 0; i < len; i++) {
         const ord = buffer[i];
         const following = i + 1 < len ? buffer[i + 1] : next;
-        const lineBreakByte = binary && (ord === 0x0d || ord === 0x0a)
-            ? ord === 0x0d
-                ? following === 0x0a
-                : (i > 0 ? buffer[i - 1] : previous) === 0x0d
-            : true;
+        const lineBreakByte = binary && (ord === 0x0d || ord === 0x0a) ? (ord === 0x0d ? following === 0x0a : (i > 0 ? buffer[i - 1] : previous) === 0x0d) : true;
         // if the char is in allowed range, then keep as is, unless it is a WS in the end of a line
-        if (QP_LITERAL[ord] &&
-            lineBreakByte &&
-            !(isWhitespace(ord) && (following === undefined || following === 0x0a || following === 0x0d))) {
+        if (QP_LITERAL[ord] && lineBreakByte && !(isWhitespace(ord) && (following === undefined || following === 0x0a || following === 0x0d))) {
             output[pos++] = ord;
             continue;
         }
@@ -114,10 +108,7 @@ export function wrap(str, lineLength) {
                 line = line.substr(0, line.length - match[0].length);
             }
             // ensure that utf-8 sequences are not split
-            while (line.length > 3 &&
-                line.length < len - pos &&
-                !line.match(/^(?:=[\da-f]{2}){1,4}$/i) &&
-                (match = line.match(/[=][\da-f]{2}$/gi))) {
+            while (line.length > 3 && line.length < len - pos && !line.match(/^(?:=[\da-f]{2}){1,4}$/i) && (match = line.match(/[=][\da-f]{2}$/gi))) {
                 code = parseInt(match[0].substr(1, 2), 16);
                 if (code < 128) {
                     break;

package/dist/esm/sendmail-transport/index.js

@@ -71,9 +71,7 @@ class SendmailTransport {
             return done(err);
         }
         // force -i to keep single dots
-        const args = this.args
-            ? ['-i'].concat(this.args).concat(envelope.to)
-            : ['-i'].concat(envelope.from ? ['-f', envelope.from] : []).concat(envelope.to);
+        const args = this.args ? ['-i'].concat(this.args).concat(envelope.to) : ['-i'].concat(envelope.from ? ['-f', envelope.from] : []).concat(envelope.to);
         const callback = (err) => {
             if (returned) {
                 // ignore any additional responses, already done

package/dist/esm/shared/index.js

@@ -217,9 +217,7 @@ export const resolveHostname = (options, callback) => {
                     return respond(err);
                 }
                 // Get all supported addresses from dns.lookup
-                const supportedAddresses = addresses
-                    ? addresses.filter(addr => isFamilySupported(addr.family)).map(addr => addr.address)
-                    : [];
+                const supportedAddresses = addresses ? addresses.filter(addr => isFamilySupported(addr.family)).map(addr => addr.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`);
@@ -549,9 +547,7 @@ export const assign = function (...args) {
             if (isProtoKey(key)) {
                 return;
             }
-            if (['tls', 'auth'].includes(key) &&
-                source[key] &&
-                typeof source[key] === 'object') {
+            if (['tls', 'auth'].includes(key) && source[key] && typeof source[key] === 'object') {
                 // tls and auth are special keys that need to be enumerated separately
                 // other objects are passed as is. Enumerating is a copy of user supplied
                 // keys just like the loop above, so it gets the same treatment

package/dist/esm/smtp-connection/http-proxy-client.js

@@ -9,7 +9,7 @@ import * as errors from '../errors.js';
 // never sends \r\n\r\n cannot grow memory unboundedly before the socket times out.
 const MAX_RESPONSE_HEADER_BYTES = 64 * 1024;
 // URL hostnames keep the brackets around an IPv6 literal, socket options and net.isIPv6 take it without
-const unbracket = (host) => typeof host === 'string' && host.startsWith('[') && host.endsWith(']') ? host.slice(1, -1) : host;
+const unbracket = (host) => (typeof host === 'string' && host.startsWith('[') && host.endsWith(']') ? host.slice(1, -1) : host);
 function httpProxyClient(proxyUrl, destinationPort, destinationHost, tlsOptions, callback) {
     if (typeof tlsOptions === 'function') {
         callback = tlsOptions;

package/dist/esm/smtp-connection/index.d.ts

@@ -245,6 +245,12 @@ export interface SMTPConnectionSendInfo extends SMTPConnectionEnvelopeInfo {
     messageSize: number;
     /** Final server response for the message */
     response: string;
+    /**
+     * Message-ID the server gave the message, with angle brackets, when its final reply names
+     * one in a known format (Microsoft 365 and Outlook.com, Amazon SES). Such a server replaces
+     * the Message-ID header, so the delivered copy carries this id instead of messageId
+     */
+    serverMessageId?: string | undefined;
 }
 /**
  * Callback for send(), receives the result once the server accepted the message. The error

package/dist/esm/smtp-connection/index.js

@@ -7,7 +7,8 @@ import crypto from 'node:crypto';
 import DataStream from './data-stream.js';
 import { PassThrough } from 'node:stream';
 import * as shared from '../shared/index.js';
-import { ERR_ACCESS_DENIED, isTransientError } from '../errors.js';
+import { parseServerMessageId } from './server-message-id.js';
+import { ERR_ACCESS_DENIED, isPermanentResponseCode, isTransientError } from '../errors.js';
 // default timeout values in ms
 const CONNECTION_TIMEOUT = 2 * 60 * 1000; // how much to wait for the connection to be established
 const SOCKET_TIMEOUT = 10 * 60 * 1000; // how much to wait for socket inactivity before disconnecting the client
@@ -361,9 +362,7 @@ class SMTPConnection extends EventEmitter {
         if (this._destroyed || this._closing) {
             return;
         }
-        const connectFn = secure
-            ? tls.connect
-            : net.connect;
+        const connectFn = secure ? tls.connect : net.connect;
         try {
             this._socket = connectFn(opts, () => this._onConnect());
             this._setupConnectionHandlers();
@@ -701,6 +700,16 @@ class SMTPConnection extends EventEmitter {
                 result.messageTime = Date.now() - envelopeTime;
                 result.messageSize = stream.outByteCount;
                 result.response = str;
+                const serverMessageId = parseServerMessageId(result.response, this.options.host);
+                if (serverMessageId) {
+                    result.serverMessageId = serverMessageId;
+                }
+                // an LMTP server answers the message once per recipient, so recipients can be
+                // refused after the envelope info was built without any rejected errors on it
+                const rejectedErrors = this._envelope?.rejectedErrors;
+                if (!result.rejectedErrors && rejectedErrors && rejectedErrors.length) {
+                    result.rejectedErrors = rejectedErrors;
+                }
                 return callback(null, result);
             });
             if (typeof message.pipe === 'function') {
@@ -928,6 +937,7 @@ class SMTPConnection extends EventEmitter {
         const responseCode = (typeof response === 'string' && Number((response.match(/^\d+/) || [])[0])) || false;
         if (responseCode) {
             err.responseCode = responseCode;
+            err.permanent = isPermanentResponseCode(responseCode);
         }
         if (command) {
             err.command = command;
@@ -970,12 +980,7 @@ class SMTPConnection extends EventEmitter {
             this.close();
             return;
         }
-        if (!failureResponse &&
-            this.stage === 'connected' &&
-            !this._responseActions.length &&
-            !this._pendingSend &&
-            !this._destroyed &&
-            !this._closing) {
+        if (!failureResponse && this.stage === 'connected' && !this._responseActions.length && !this._pendingSend && !this._destroyed && !this._closing) {
             // nothing was waiting for the server, so this is the server ending an idle session
             // (usually after its idle timeout), not a failure
             this.logger.info({
@@ -1196,9 +1201,7 @@ class SMTPConnection extends EventEmitter {
         const args = [];
         let useSmtpUtf8 = false;
         this._envelope = (envelope || {});
-        this._envelope.from = ((this._envelope.from && this._envelope.from.address) || this._envelope.from || '')
-            .toString()
-            .trim();
+        this._envelope.from = ((this._envelope.from && this._envelope.from.address) || this._envelope.from || '').toString().trim();
         this._envelope.to = []
             .concat(this._envelope.to || [])
             .map(to => ((to && to.address) || to || '').toString().trim());

package/dist/esm/smtp-connection/server-message-id.d.ts

@@ -0,0 +1,14 @@
+/**
+ * Reads the Message-ID a receiving server gave the message out of its final 250 reply. Some
+ * servers replace the Message-ID header of a submitted message with one of their own, and
+ * the copy the recipients and the sent folder get carries that one instead of the id the
+ * message was built with. Only replies in a format known to carry such an id are read.
+ */
+/**
+ * Reads the server assigned Message-ID out of the final reply to a message
+ *
+ * @param response Final server reply for the message
+ * @param [host] Hostname the connection was made to, SES replies are only read for an SES host
+ * @returns The Message-ID with its angle brackets, or undefined when the reply names none
+ */
+export declare function parseServerMessageId(response: string | undefined, host?: string): string | undefined;

package/dist/esm/smtp-connection/server-message-id.js

@@ -0,0 +1,50 @@
+/**
+ * Reads the Message-ID a receiving server gave the message out of its final 250 reply. Some
+ * servers replace the Message-ID header of a submitted message with one of their own, and
+ * the copy the recipients and the sent folder get carries that one instead of the id the
+ * message was built with. Only replies in a format known to carry such an id are read.
+ */
+// Microsoft 365 and Outlook.com: "250 2.0.0 OK <id@host.prod.outlook.com> [Hostname=...]"
+const OUTLOOK_REPLY = /^250 2\.0\.0 OK (<[^<>\s]+\.prod\.outlook\.com>)/i;
+// Amazon SES: "250 Ok 0100018b5c3c0a4f-...-000000", the local part of the Message-ID it sets
+const SES_REPLY = /^250 Ok ([0-9a-f]+(?:-[0-9a-f]+)+)$/i;
+// an AWS region name such as us-east-1 or ap-southeast-2
+const AWS_REGION = /^[a-z]{2}(?:-[a-z]+)+-\d+$/;
+/**
+ * Finds the AWS region an SES SMTP endpoint is in from its hostname, such as
+ * email-smtp.eu-west-1.amazonaws.com or a VPC endpoint name under it
+ *
+ * @param host SMTP hostname
+ * @returns Region name, or undefined for a host outside amazonaws.com and awsapps.com
+ */
+function sesRegion(host) {
+    const labels = host.toLowerCase().replace(/\.$/, '').split('.');
+    const domain = labels.slice(-2).join('.');
+    if (domain !== 'amazonaws.com' && domain !== 'awsapps.com') {
+        return undefined;
+    }
+    return labels.slice(0, -2).find(label => AWS_REGION.test(label));
+}
+/**
+ * Reads the server assigned Message-ID out of the final reply to a message
+ *
+ * @param response Final server reply for the message
+ * @param [host] Hostname the connection was made to, SES replies are only read for an SES host
+ * @returns The Message-ID with its angle brackets, or undefined when the reply names none
+ */
+export function parseServerMessageId(response, host) {
+    const reply = (response || '').toString().trim();
+    const outlook = reply.match(OUTLOOK_REPLY);
+    if (outlook) {
+        return outlook[1];
+    }
+    const ses = reply.match(SES_REPLY);
+    if (ses && host) {
+        const region = sesRegion(host);
+        if (region) {
+            // the SES Message-ID domain is email.amazonses.com in us-east-1 and the region elsewhere
+            return '<' + ses[1].toLowerCase() + '@' + (region === 'us-east-1' ? 'email' : region) + '.amazonses.com>';
+        }
+    }
+    return undefined;
+}

package/dist/esm/smtp-pool/index.d.ts

@@ -110,6 +110,17 @@ declare class SMTPPool extends EventEmitter {
      * Returns true if there are free slots in the queue
      */
     isIdle(): boolean;
+    /**
+     * Counts the messages the pool has not finished with yet: the ones waiting in the queue
+     * plus the ones a connection is transmitting right now. isIdle() only tells whether the
+     * pool can take another message, it is already true while a message is still being sent,
+     * so use this to check that nothing would be lost by closing the pool. A message that is
+     * re-queued after its connection dropped is counted until its callback runs, also while it waits to be put back on the queue, and
+     * it is no longer counted by the time its callback runs.
+     *
+     * @returns Number of queued and in-flight messages
+     */
+    pendingCount(): number;
     /**
      * Verifies SMTP configuration
      *

package/dist/esm/smtp-pool/index.js

@@ -62,6 +62,7 @@ class SMTPPool extends EventEmitter {
         this._queue = [];
         this._connections = [];
         this._connectionCounter = 0;
+        this._pending = 0;
         this.idling = true;
         setImmediate(() => {
             if (this.idling) {
@@ -94,10 +95,20 @@ class SMTPPool extends EventEmitter {
             setImmediate(() => callback(err));
             return false;
         }
+        // counted until the callback runs, whichever path runs it: delivered, failed, requeued
+        // until it gives up, or drained by close()
+        let counted = true;
+        this._pending++;
         this._queue.push({
             mail,
             requeueAttempts: 0,
-            callback
+            callback: (err, info) => {
+                if (counted) {
+                    counted = false;
+                    this._pending--;
+                }
+                callback(err, info);
+            }
         });
         if (this.idling && this._queue.length >= this.options.maxConnections) {
             this.idling = false;
@@ -441,6 +452,19 @@ class SMTPPool extends EventEmitter {
     isIdle() {
         return this.idling;
     }
+    /**
+     * Counts the messages the pool has not finished with yet: the ones waiting in the queue
+     * plus the ones a connection is transmitting right now. isIdle() only tells whether the
+     * pool can take another message, it is already true while a message is still being sent,
+     * so use this to check that nothing would be lost by closing the pool. A message that is
+     * re-queued after its connection dropped is counted until its callback runs, also while it waits to be put back on the queue, and
+     * it is no longer counted by the time its callback runs.
+     *
+     * @returns Number of queued and in-flight messages
+     */
+    pendingCount() {
+        return this._pending;
+    }
     verify(callback) {
         let promise;
         if (!callback) {

package/dist/esm/smtp-pool/pool-resource.js

@@ -19,8 +19,7 @@ export default class PoolResource extends EventEmitter {
             switch ((this.options.auth.type || '').toString().toUpperCase()) {
                 case 'OAUTH2': {
                     const oauth2 = new XOAuth2(this.options.auth, this.logger);
-                    oauth2.provisionCallback =
-                        (this.pool.mailer && this.pool.mailer.get('oauth2_provision_cb')) || oauth2.provisionCallback;
+                    oauth2.provisionCallback = (this.pool.mailer && this.pool.mailer.get('oauth2_provision_cb')) || oauth2.provisionCallback;
                     this.auth = {
                         type: 'OAUTH2',
                         user: this.options.auth.user,
@@ -208,9 +207,7 @@ export default class PoolResource extends EventEmitter {
                     this.connection.close();
                     return;
                 }
-                if ((err.code === errors.EENVELOPE || err.code === errors.EMESSAGE) &&
-                    err.responseCode !== 421 &&
-                    !this.connection._destroyed) {
+                if ((err.code === errors.EENVELOPE || err.code === errors.EMESSAGE) && err.responseCode !== 421 && !this.connection._destroyed) {
                     // The server refused this message, the connection itself is fine. Reset the
                     // session and keep using it instead of opening a new one
                     this.connection.reset(resetErr => {