@aglyn/plugins-outreach 1.0.0-beta.213 → 1.0.0-beta.215

package/src/lib/transport/rfc5322.js

@@ -292,7 +292,7 @@ const isAscii = (value)=>isPrintableAscii(value);
     return body.split(CRLF).every((line)=>isAscii(line) && line.length <= MAX_LINE);
 }
 /** Builds the message. Throws {@link Rfc5322MessageError} on anything unsafe. */ export function buildRfc5322Message(message, options = {}) {
-    var _options_messageIdDomain, _options_messageIdLocalPart, _options_date;
+    var _options_messageIdDomain, _options_messageIdLocalPart, _options_date, _options_boundary;
     const from = normalizeAddress(message.from, 'From');
     const to = normalizeAddress(message.to, 'To');
     const subject = subjectTokens(message.subject);
@@ -303,9 +303,7 @@ const isAscii = (value)=>isPrintableAscii(value);
         throw new Rfc5322MessageError('invalid-message-id', 'The Message-ID would not be valid.');
     }
     const messageId = `<${local}@${domain}>`;
-    const body = canonicalBody(message.text);
-    const sevenBit = isSevenBitSafe(body);
-    const lines = [
+    const headers = [
         foldHeader('From', formatAddress(from)),
         foldHeader('To', formatAddress(to)),
         ...subject.length ? [
@@ -316,17 +314,54 @@ const isAscii = (value)=>isPrintableAscii(value);
         `Date: ${formatRfc5322Date((_options_date = options.date) != null ? _options_date : new Date())}`,
         `Message-ID: ${messageId}`,
         ...extras.map(([name, value])=>foldHeader(name, spaceTokens(value))),
-        'MIME-Version: 1.0',
-        'Content-Type: text/plain; charset=UTF-8',
-        `Content-Transfer-Encoding: ${sevenBit ? '7bit' : 'quoted-printable'}`
+        'MIME-Version: 1.0'
     ];
-    const encodedBody = sevenBit ? body : encodeQuotedPrintable(body);
+    const text = mimePart('text/plain', message.text);
+    const html = typeof message.html === 'string' && message.html.trim() ? mimePart('text/html', message.html) : null;
+    if (!html) {
+        return {
+            raw: `${[
+                ...headers,
+                ...text.headers
+            ].join(CRLF)}${CRLF}${CRLF}${text.body}`,
+            messageId,
+            subject: message.subject.trim()
+        };
+    }
+    /*
+   * RFC 2046 §5.1.4: alternatives in increasing order of preference, so the
+   * plain text comes first and a client that can show HTML shows the HTML.
+   * The boundary is a UUID's characters behind a prefix, which no
+   * quoted-printable or 7bit body line can contain in full.
+   */ const boundary = (_options_boundary = options.boundary) != null ? _options_boundary : `aglyn-alt-${randomUUID()}`;
+    if (!/^[A-Za-z0-9'()+_,./:=?-]{1,70}$/.test(boundary)) {
+        throw new Rfc5322MessageError('invalid-header', 'The multipart boundary would not be valid.');
+    }
+    const part = (built)=>`--${boundary}${CRLF}${built.headers.join(CRLF)}${CRLF}${CRLF}${built.body}`;
     return {
-        raw: `${lines.join(CRLF)}${CRLF}${CRLF}${encodedBody}`,
+        raw: `${[
+            ...headers,
+            `Content-Type: multipart/alternative; boundary="${boundary}"`
+        ].join(CRLF)}${CRLF}${CRLF}` + `${part(text)}${part(html)}--${boundary}--${CRLF}`,
         messageId,
         subject: message.subject.trim()
     };
 }
+/**
+ * One body with its content headers: `7bit` when it is ASCII with no line
+ * over 998 octets, `quoted-printable` otherwise. The body ends with a CRLF,
+ * which is what puts a following boundary on a line of its own.
+ */ function mimePart(type, content) {
+    const body = canonicalBody(content);
+    const sevenBit = isSevenBitSafe(body);
+    return {
+        headers: [
+            `Content-Type: ${type}; charset=UTF-8`,
+            `Content-Transfer-Encoding: ${sevenBit ? '7bit' : 'quoted-printable'}`
+        ],
+        body: sevenBit ? body : encodeQuotedPrintable(body)
+    };
+}
 /** The `raw` field Gmail's `messages.send` takes: the message, base64url. */ export function encodeGmailRawMessage(raw) {
     return Buffer.from(raw, 'utf8').toString('base64url');
 }

package/src/lib/transport/rfc5322.js.map

@@ -1 +1 @@
-{"version":3,"sources":["../../../../../../../libs/plugins/outreach/src/lib/transport/rfc5322.ts"],"sourcesContent":["/**\n * @license\n * Copyright 2026 Aglyn LLC\n *\n * Licensed under the Apache License, Version 2.0 (the \"License\");\n * you may not use this file except in compliance with the License.\n * You may obtain a copy of the License at\n *\n *   http://www.apache.org/licenses/LICENSE-2.0\n *\n * Unless required by applicable law or agreed to in writing, software\n * distributed under the License is distributed on an \"AS IS\" BASIS,\n * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.\n * See the License for the specific language governing permissions and\n * limitations under the License.\n */\n\nimport { LIST_UNSUBSCRIBE_ONE_CLICK } from '@aglyn/shared-util-email/list-unsubscribe'\nimport { randomUUID } from 'node:crypto'\n\n/**\n * AN OUTREACH MESSAGE AS RFC 5322 TEXT (AGL-2978).\n *\n * Gmail's `messages.send` takes the whole message, headers and body, as one\n * base64url string. This module writes that string for the one kind of mail\n * Outreach sends: a plain-text message from one person to one person.\n *\n * ## What it writes, and what it never does\n *\n * - `From` and `To` with display names — quoted when ASCII, RFC 2047\n *   encoded-words when not.\n * - `Subject`, RFC 2047 when it is not plain ASCII, folded under 78 columns.\n * - `Date` in RFC 5322 form, UTC.\n * - `Message-ID` `<uuid@domain>`, the domain being the From address's unless\n *   the caller names one, so the id belongs to the domain the mail is from.\n * - `MIME-Version: 1.0` and `Content-Type: text/plain; charset=UTF-8`.\n * - The caller's `In-Reply-To`, `References`, `Reply-To`, `List-Unsubscribe`\n *   and `List-Unsubscribe-Post`, plus any `X-` header.\n * - CRLF line endings throughout. The body goes as `7bit` when it is ASCII\n *   with no line over 998 octets, and `quoted-printable` otherwise.\n *\n * No HTML part, no tracking pixel, no rewritten links, no open or click\n * beacon of any kind: the body the caller composed is the body that is sent.\n *\n * ## Refusals\n *\n * A header value containing a line break is a header INJECTION, whoever typed\n * it — a merge field holding a CRLF would append headers of its choosing — so\n * every value is checked and a violation throws {@link Rfc5322MessageError}\n * rather than being cleaned up. Structural headers (`From`, `To`, `Cc`,\n * `Bcc`, `Subject`, `Date`, `Message-ID`, the MIME fields, …) cannot be passed\n * in `headers`: this module writes them, exactly once.\n *\n * Addresses must be ASCII. An internationalized mailbox needs SMTPUTF8 end to\n * end, which a one-to-one prospecting message cannot count on, so one is\n * refused rather than sent in a form some hop would mangle.\n */\n\n/** One mailbox, optionally with the name people see. */\nexport interface OutreachMailAddress {\n  address: string\n  name?: string | null\n}\n\n/** An address as a bare string, or with a display name. */\nexport type OutreachMailAddressInput = string | OutreachMailAddress\n\n/**\n * A composed message, as the sequence engine hands it over: who it is from,\n * who it is to, the subject, the plain-text body, and any extra headers.\n */\nexport interface OutreachComposedMessage {\n  from: OutreachMailAddressInput\n  to: OutreachMailAddressInput\n  subject: string\n  text: string\n  /**\n   * `In-Reply-To`, `References`, `Reply-To`, `List-Unsubscribe`,\n   * `List-Unsubscribe-Post`, or an `X-` header. A null, undefined or empty\n   * value is omitted.\n   */\n  headers?: Readonly<Record<string, string | null | undefined>>\n}\n\nexport interface BuildRfc5322Options {\n  /** The `Date` header. Now when omitted. */\n  date?: Date\n  /** The Message-ID's left part. A random UUID when omitted. */\n  messageIdLocalPart?: string\n  /** The Message-ID's domain. The From address's domain when omitted. */\n  messageIdDomain?: string\n}\n\nexport interface BuiltRfc5322Message {\n  /** The message, CRLF line endings, ready to base64url-encode. */\n  raw: string\n  /** The `Message-ID`, angle brackets included, to thread replies against. */\n  messageId: string\n  /** The subject as written, trimmed: what the recipient sees. */\n  subject: string\n}\n\nexport type Rfc5322MessageErrorCode =\n  | 'invalid-address'\n  | 'invalid-subject'\n  | 'invalid-header'\n  | 'reserved-header'\n  | 'unsupported-header'\n  | 'invalid-message-id'\n\nexport class Rfc5322MessageError extends Error {\n  readonly code: Rfc5322MessageErrorCode\n\n  constructor(code: Rfc5322MessageErrorCode, message: string) {\n    super(message)\n    this.name = 'Rfc5322MessageError'\n    this.code = code\n  }\n}\n\nconst CRLF = '\\r\\n'\n\n/** RFC 5322 recommends lines of at most 78 characters. */\nconst FOLD_AT = 78\n\n/** RFC 5322's hard limit on a line, excluding the CRLF. */\nconst MAX_LINE = 998\n\n/** A pragmatic ASCII addr-spec: no whitespace, specials or control characters. */\nconst ADDRESS = /^[A-Za-z0-9.!#$%&'*+/=?^_`{|}~-]+@[A-Za-z0-9](?:[A-Za-z0-9-]*[A-Za-z0-9])?(?:\\.[A-Za-z0-9](?:[A-Za-z0-9-]*[A-Za-z0-9])?)+$/\n\n/** A header field name: printable ASCII, no colon (RFC 5322 §3.6.8). */\nconst FIELD_NAME = /^[!-9;-~]+$/\n\n/**\n * Whether text holds a character below space other than tab, or DEL. Finding\n * one is the point: a CR or LF in a header value is a header injection.\n */\nfunction hasControlCharacter(value: string): boolean {\n  for (let index = 0; index < value.length; index += 1) {\n    const code = value.charCodeAt(index)\n    if ((code < 32 && code !== 9) || code === 127) return true\n  }\n  return false\n}\n\n/** Whether text is printable ASCII and tabs only. */\nfunction isPrintableAscii(value: string): boolean {\n  for (let index = 0; index < value.length; index += 1) {\n    const code = value.charCodeAt(index)\n    if (code !== 9 && (code < 32 || code > 126)) return false\n  }\n  return true\n}\n\n/** A Message-ID's left part, kept to the characters a UUID and a caller need. */\nconst MESSAGE_ID_LOCAL = /^[A-Za-z0-9][A-Za-z0-9._-]{0,127}$/\n\n/**\n * Headers the builder writes itself. Passing one in `headers` is refused, so\n * no message can carry two `From` fields or smuggle a second `Content-Type`.\n */\nconst RESERVED_HEADERS = new Set([\n  'from',\n  'sender',\n  'to',\n  'cc',\n  'bcc',\n  'subject',\n  'date',\n  'message-id',\n  'mime-version',\n  'content-type',\n  'content-transfer-encoding',\n  'content-disposition',\n  'return-path',\n  'received',\n  'dkim-signature',\n])\n\n/** The extra headers a caller may set, spelled as they are written. */\nconst EXTRA_HEADERS: Record<string, string> = {\n  'in-reply-to': 'In-Reply-To',\n  references: 'References',\n  'reply-to': 'Reply-To',\n  'list-unsubscribe': 'List-Unsubscribe',\n  'list-unsubscribe-post': 'List-Unsubscribe-Post',\n}\n\n/**\n * The one value RFC 8058 defines for `List-Unsubscribe-Post`, re-exported\n * from the module campaigns and sequences share (AGL-3307).\n */\nexport { LIST_UNSUBSCRIBE_ONE_CLICK }\n\nconst isAscii = (value: string) => isPrintableAscii(value)\n\n/** The address, validated and in its written form. */\nfunction normalizeAddress(input: OutreachMailAddressInput, field: string): OutreachMailAddress {\n  const record = typeof input === 'string' ? { address: input } : input\n  const address = String(record?.address ?? '').trim()\n  if (!address || address.length > 254 || !ADDRESS.test(address)) {\n    throw new Rfc5322MessageError('invalid-address', `The ${field} address is not a valid ASCII email address.`)\n  }\n  const name = typeof record?.name === 'string' ? record.name.trim() : ''\n  if (hasControlCharacter(name)) {\n    throw new Rfc5322MessageError('invalid-address', `The ${field} display name contains a control character.`)\n  }\n  return { address, name }\n}\n\n/**\n * RFC 2047 `B` encoded-words for a UTF-8 string, each at most 75 characters\n * and never splitting a character between two words.\n */\nexport function encodeRfc2047Words(value: string): string[] {\n  // 42 bytes base64-encode to 56 characters; with `=?UTF-8?B?` and `?=` a\n  // word is 68 — inside the 75 the RFC allows, and short enough that the\n  // first word still fits on a `Subject: ` line within 78 columns.\n  const maxBytes = 42\n  const words: string[] = []\n  let chunk = ''\n  let chunkBytes = 0\n  for (const character of value) {\n    const bytes = Buffer.byteLength(character, 'utf8')\n    if (chunkBytes + bytes > maxBytes && chunk) {\n      words.push(chunk)\n      chunk = ''\n      chunkBytes = 0\n    }\n    chunk += character\n    chunkBytes += bytes\n  }\n  if (chunk) words.push(chunk)\n  return words.map((word) => `=?UTF-8?B?${Buffer.from(word, 'utf8').toString('base64')}?=`)\n}\n\n/** A quoted-string, escaping the two characters RFC 5322 requires. */\nconst quoted = (value: string) => `\"${value.replace(/([\"\\\\])/g, '\\\\$1')}\"`\n\n/**\n * Whether ASCII text would read as an encoded-word to a mail client, which\n * decodes `=?…?=` wherever it appears in a header.\n */\nconst looksEncoded = (value: string) => /=\\?[^?]*\\?[bBqQ]\\?[^?]*\\?=/.test(value)\n\n/**\n * `Name <address>` as tokens to fold, the name quoted or encoded as it needs.\n * The angle-address is its own token, so a long name folds before it.\n */\nfunction formatAddress(address: OutreachMailAddress): string[] {\n  if (!address.name) return [address.address]\n  const name =\n    isAscii(address.name) && !looksEncoded(address.name)\n      ? [quoted(address.name)]\n      : encodeRfc2047Words(address.name)\n  return [...name, `<${address.address}>`]\n}\n\n/**\n * A value split at single spaces for folding, with every run of spaces kept:\n * an empty token is merged into the next one, so joining the tokens with one\n * space gives the value back exactly and no fold ever leaves a line of only\n * whitespace.\n */\nfunction spaceTokens(value: string): string[] {\n  const tokens: string[] = []\n  let pending = ''\n  for (const part of value.split(' ')) {\n    if (!part) {\n      pending += ' '\n      continue\n    }\n    tokens.push(`${pending}${part}`)\n    pending = ''\n  }\n  return tokens\n}\n\n/**\n * One header written as folded lines: `tokens` are joined by a space, and a\n * token that would push its line past 78 columns starts the next line.\n */\nfunction foldHeader(name: string, tokens: readonly string[]): string {\n  const lines: string[] = []\n  let line = `${name}:`\n  for (const token of tokens) {\n    if (line.length + 1 + token.length > FOLD_AT && line !== `${name}:`) {\n      lines.push(line)\n      line = ` ${token}`\n    } else {\n      line += ` ${token}`\n    }\n  }\n  lines.push(line)\n  for (const written of lines) {\n    if (written.length > MAX_LINE) {\n      throw new Rfc5322MessageError('invalid-header', `The ${name} header has a line longer than ${MAX_LINE} characters.`)\n    }\n  }\n  return lines.join(CRLF)\n}\n\n/** The subject, as words to fold: plain ASCII split on spaces, or encoded-words. */\nfunction subjectTokens(subject: string): string[] {\n  if (typeof subject !== 'string') {\n    throw new Rfc5322MessageError('invalid-subject', 'The subject must be text.')\n  }\n  if (hasControlCharacter(subject)) {\n    throw new Rfc5322MessageError('invalid-subject', 'The subject contains a line break or control character.')\n  }\n  const trimmed = subject.trim()\n  if (!trimmed) return []\n  if (isAscii(trimmed) && !looksEncoded(trimmed)) {\n    const words = spaceTokens(trimmed)\n    if (words.every((word) => `Subject: ${word}`.length <= MAX_LINE)) return words\n  }\n  return encodeRfc2047Words(trimmed)\n}\n\n/** RFC 5322 §3.3 date-time, in UTC. */\nexport function formatRfc5322Date(date: Date): string {\n  const days = ['Sun', 'Mon', 'Tue', 'Wed', 'Thu', 'Fri', 'Sat']\n  const months = ['Jan', 'Feb', 'Mar', 'Apr', 'May', 'Jun', 'Jul', 'Aug', 'Sep', 'Oct', 'Nov', 'Dec']\n  const pad = (value: number) => String(value).padStart(2, '0')\n  return (\n    `${days[date.getUTCDay()]}, ${pad(date.getUTCDate())} ${months[date.getUTCMonth()]} ` +\n    `${date.getUTCFullYear()} ${pad(date.getUTCHours())}:${pad(date.getUTCMinutes())}:` +\n    `${pad(date.getUTCSeconds())} +0000`\n  )\n}\n\n/** The extra headers, validated, named as written, in the order given. */\nfunction extraHeaders(headers: OutreachComposedMessage['headers']): Array<[string, string]> {\n  const written: Array<[string, string]> = []\n  const seen = new Set<string>()\n  for (const [rawName, rawValue] of Object.entries(headers ?? {})) {\n    if (rawValue === null || rawValue === undefined || rawValue === '') continue\n    const name = String(rawName).trim()\n    const lower = name.toLowerCase()\n    if (!FIELD_NAME.test(name)) {\n      throw new Rfc5322MessageError('invalid-header', 'A header name is not a valid field name.')\n    }\n    if (RESERVED_HEADERS.has(lower)) {\n      throw new Rfc5322MessageError('reserved-header', `The ${name} header is written by the message builder and cannot be set.`)\n    }\n    const canonical = EXTRA_HEADERS[lower] ?? (lower.startsWith('x-') ? name : null)\n    if (!canonical) {\n      throw new Rfc5322MessageError('unsupported-header', `The ${name} header is not one a sequence sends.`)\n    }\n    if (seen.has(lower)) {\n      throw new Rfc5322MessageError('invalid-header', `The ${name} header is given twice.`)\n    }\n    const value = String(rawValue).trim()\n    if (hasControlCharacter(value) || !isAscii(value)) {\n      throw new Rfc5322MessageError('invalid-header', `The ${name} header value must be printable ASCII on one line.`)\n    }\n    seen.add(lower)\n    written.push([canonical, value])\n  }\n  const post = written.find(([name]) => name === 'List-Unsubscribe-Post')\n  if (post) {\n    const unsubscribe = written.find(([name]) => name === 'List-Unsubscribe')\n    if (post[1] !== LIST_UNSUBSCRIBE_ONE_CLICK || !unsubscribe || !/<https:\\/\\/[^>]+>/.test(unsubscribe[1])) {\n      throw new Rfc5322MessageError(\n        'invalid-header',\n        `List-Unsubscribe-Post must be \"${LIST_UNSUBSCRIBE_ONE_CLICK}\" beside a List-Unsubscribe with an https address (RFC 8058).`,\n      )\n    }\n  }\n  return written\n}\n\n/** Line breaks of any kind, as CRLF, ending with one. */\nfunction canonicalBody(text: string): string {\n  const normalized = String(text ?? '').replace(/\\r\\n|\\r|\\n/g, CRLF)\n  return normalized.endsWith(CRLF) ? normalized : `${normalized}${CRLF}`\n}\n\n/**\n * RFC 2045 §6.7 quoted-printable for CRLF-separated text: `=`, non-ASCII\n * bytes and control characters as `=XX`, whitespace at a line's end encoded,\n * and soft breaks keeping every encoded line to 76 characters.\n */\nexport function encodeQuotedPrintable(text: string): string {\n  const hex = (byte: number) => `=${byte.toString(16).toUpperCase().padStart(2, '0')}`\n  return text\n    .split(CRLF)\n    .map((line) => {\n      const bytes = Buffer.from(line, 'utf8')\n      let encoded = ''\n      let current = ''\n      bytes.forEach((byte, index) => {\n        const last = index === bytes.length - 1\n        const literal =\n          (byte >= 33 && byte <= 126 && byte !== 61) || ((byte === 32 || byte === 9) && !last)\n        const token = literal ? String.fromCharCode(byte) : hex(byte)\n        if (current.length + token.length > 75) {\n          encoded += `${current}=${CRLF}`\n          current = ''\n        }\n        current += token\n      })\n      return encoded + current\n    })\n    .join(CRLF)\n}\n\n/** Whether the body can travel as 7bit: ASCII, and no line over 998 octets. */\nfunction isSevenBitSafe(body: string): boolean {\n  return body.split(CRLF).every((line) => isAscii(line) && line.length <= MAX_LINE)\n}\n\n/** Builds the message. Throws {@link Rfc5322MessageError} on anything unsafe. */\nexport function buildRfc5322Message(\n  message: OutreachComposedMessage,\n  options: BuildRfc5322Options = {},\n): BuiltRfc5322Message {\n  const from = normalizeAddress(message.from, 'From')\n  const to = normalizeAddress(message.to, 'To')\n  const subject = subjectTokens(message.subject)\n  const extras = extraHeaders(message.headers)\n\n  const domain = (options.messageIdDomain ?? from.address.slice(from.address.lastIndexOf('@') + 1)).trim()\n  const local = options.messageIdLocalPart ?? randomUUID()\n  if (!MESSAGE_ID_LOCAL.test(local) || !ADDRESS.test(`id@${domain}`)) {\n    throw new Rfc5322MessageError('invalid-message-id', 'The Message-ID would not be valid.')\n  }\n  const messageId = `<${local}@${domain}>`\n\n  const body = canonicalBody(message.text)\n  const sevenBit = isSevenBitSafe(body)\n\n  const lines = [\n    foldHeader('From', formatAddress(from)),\n    foldHeader('To', formatAddress(to)),\n    ...(subject.length ? [foldHeader('Subject', subject)] : ['Subject:']),\n    `Date: ${formatRfc5322Date(options.date ?? new Date())}`,\n    `Message-ID: ${messageId}`,\n    ...extras.map(([name, value]) => foldHeader(name, spaceTokens(value))),\n    'MIME-Version: 1.0',\n    'Content-Type: text/plain; charset=UTF-8',\n    `Content-Transfer-Encoding: ${sevenBit ? '7bit' : 'quoted-printable'}`,\n  ]\n  const encodedBody = sevenBit ? body : encodeQuotedPrintable(body)\n  return {\n    raw: `${lines.join(CRLF)}${CRLF}${CRLF}${encodedBody}`,\n    messageId,\n    subject: message.subject.trim(),\n  }\n}\n\n/** The `raw` field Gmail's `messages.send` takes: the message, base64url. */\nexport function encodeGmailRawMessage(raw: string): string {\n  return Buffer.from(raw, 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+{"version":3,"sources":["../../../../../../../libs/plugins/outreach/src/lib/transport/rfc5322.ts"],"sourcesContent":["/**\n * @license\n * Copyright 2026 Aglyn LLC\n *\n * Licensed under the Apache License, Version 2.0 (the \"License\");\n * you may not use this file except in compliance with the License.\n * You may obtain a copy of the License at\n *\n *   http://www.apache.org/licenses/LICENSE-2.0\n *\n * Unless required by applicable law or agreed to in writing, software\n * distributed under the License is distributed on an \"AS IS\" BASIS,\n * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.\n * See the License for the specific language governing permissions and\n * limitations under the License.\n */\n\nimport { LIST_UNSUBSCRIBE_ONE_CLICK } from '@aglyn/shared-util-email/list-unsubscribe'\nimport { randomUUID } from 'node:crypto'\n\n/**\n * AN OUTREACH MESSAGE AS RFC 5322 TEXT (AGL-2978).\n *\n * Gmail's `messages.send` takes the whole message, headers and body, as one\n * base64url string. This module writes that string for the one kind of mail\n * Outreach sends: a plain-text message from one person to one person.\n *\n * ## What it writes, and what it never does\n *\n * - `From` and `To` with display names — quoted when ASCII, RFC 2047\n *   encoded-words when not.\n * - `Subject`, RFC 2047 when it is not plain ASCII, folded under 78 columns.\n * - `Date` in RFC 5322 form, UTC.\n * - `Message-ID` `<uuid@domain>`, the domain being the From address's unless\n *   the caller names one, so the id belongs to the domain the mail is from.\n * - `MIME-Version: 1.0` and `Content-Type: text/plain; charset=UTF-8` —\n *   or, for a sequence that counts opens (AGL-3395), `multipart/alternative`\n *   holding that same plain-text part and the caller's HTML part after it.\n * - The caller's `In-Reply-To`, `References`, `Reply-To`, `List-Unsubscribe`\n *   and `List-Unsubscribe-Post`, plus any `X-` header.\n * - CRLF line endings throughout. The body goes as `7bit` when it is ASCII\n *   with no line over 998 octets, and `quoted-printable` otherwise.\n *\n * Nothing is added to what the caller composed: no HTML part it did not\n * pass, no image, no rewritten link. The body the caller composed is the\n * body that is sent.\n *\n * ## Refusals\n *\n * A header value containing a line break is a header INJECTION, whoever typed\n * it — a merge field holding a CRLF would append headers of its choosing — so\n * every value is checked and a violation throws {@link Rfc5322MessageError}\n * rather than being cleaned up. Structural headers (`From`, `To`, `Cc`,\n * `Bcc`, `Subject`, `Date`, `Message-ID`, the MIME fields, …) cannot be passed\n * in `headers`: this module writes them, exactly once.\n *\n * Addresses must be ASCII. An internationalized mailbox needs SMTPUTF8 end to\n * end, which a one-to-one prospecting message cannot count on, so one is\n * refused rather than sent in a form some hop would mangle.\n */\n\n/** One mailbox, optionally with the name people see. */\nexport interface OutreachMailAddress {\n  address: string\n  name?: string | null\n}\n\n/** An address as a bare string, or with a display name. */\nexport type OutreachMailAddressInput = string | OutreachMailAddress\n\n/**\n * A composed message, as the sequence engine hands it over: who it is from,\n * who it is to, the subject, the plain-text body, and any extra headers.\n */\nexport interface OutreachComposedMessage {\n  from: OutreachMailAddressInput\n  to: OutreachMailAddressInput\n  subject: string\n  text: string\n  /**\n   * An HTML alternative to `text` (AGL-3395). Absent — every send of a\n   * sequence that does not count opens — sends `text` alone as\n   * `text/plain`, exactly as before.\n   */\n  html?: string | null\n  /**\n   * `In-Reply-To`, `References`, `Reply-To`, `List-Unsubscribe`,\n   * `List-Unsubscribe-Post`, or an `X-` header. A null, undefined or empty\n   * value is omitted.\n   */\n  headers?: Readonly<Record<string, string | null | undefined>>\n}\n\nexport interface BuildRfc5322Options {\n  /** The `Date` header. Now when omitted. */\n  date?: Date\n  /** The Message-ID's left part. A random UUID when omitted. */\n  messageIdLocalPart?: string\n  /** The Message-ID's domain. The From address's domain when omitted. */\n  messageIdDomain?: string\n  /** The `multipart/alternative` boundary. A random one when omitted. */\n  boundary?: string\n}\n\nexport interface BuiltRfc5322Message {\n  /** The message, CRLF line endings, ready to base64url-encode. */\n  raw: string\n  /** The `Message-ID`, angle brackets included, to thread replies against. */\n  messageId: string\n  /** The subject as written, trimmed: what the recipient sees. */\n  subject: string\n}\n\nexport type Rfc5322MessageErrorCode =\n  | 'invalid-address'\n  | 'invalid-subject'\n  | 'invalid-header'\n  | 'reserved-header'\n  | 'unsupported-header'\n  | 'invalid-message-id'\n\nexport class Rfc5322MessageError extends Error {\n  readonly code: Rfc5322MessageErrorCode\n\n  constructor(code: Rfc5322MessageErrorCode, message: string) {\n    super(message)\n    this.name = 'Rfc5322MessageError'\n    this.code = code\n  }\n}\n\nconst CRLF = '\\r\\n'\n\n/** RFC 5322 recommends lines of at most 78 characters. */\nconst FOLD_AT = 78\n\n/** RFC 5322's hard limit on a line, excluding the CRLF. */\nconst MAX_LINE = 998\n\n/** A pragmatic ASCII addr-spec: no whitespace, specials or control characters. */\nconst ADDRESS = /^[A-Za-z0-9.!#$%&'*+/=?^_`{|}~-]+@[A-Za-z0-9](?:[A-Za-z0-9-]*[A-Za-z0-9])?(?:\\.[A-Za-z0-9](?:[A-Za-z0-9-]*[A-Za-z0-9])?)+$/\n\n/** A header field name: printable ASCII, no colon (RFC 5322 §3.6.8). */\nconst FIELD_NAME = /^[!-9;-~]+$/\n\n/**\n * Whether text holds a character below space other than tab, or DEL. Finding\n * one is the point: a CR or LF in a header value is a header injection.\n */\nfunction hasControlCharacter(value: string): boolean {\n  for (let index = 0; index < value.length; index += 1) {\n    const code = value.charCodeAt(index)\n    if ((code < 32 && code !== 9) || code === 127) return true\n  }\n  return false\n}\n\n/** Whether text is printable ASCII and tabs only. */\nfunction isPrintableAscii(value: string): boolean {\n  for (let index = 0; index < value.length; index += 1) {\n    const code = value.charCodeAt(index)\n    if (code !== 9 && (code < 32 || code > 126)) return false\n  }\n  return true\n}\n\n/** A Message-ID's left part, kept to the characters a UUID and a caller need. */\nconst MESSAGE_ID_LOCAL = /^[A-Za-z0-9][A-Za-z0-9._-]{0,127}$/\n\n/**\n * Headers the builder writes itself. Passing one in `headers` is refused, so\n * no message can carry two `From` fields or smuggle a second `Content-Type`.\n */\nconst RESERVED_HEADERS = new Set([\n  'from',\n  'sender',\n  'to',\n  'cc',\n  'bcc',\n  'subject',\n  'date',\n  'message-id',\n  'mime-version',\n  'content-type',\n  'content-transfer-encoding',\n  'content-disposition',\n  'return-path',\n  'received',\n  'dkim-signature',\n])\n\n/** The extra headers a caller may set, spelled as they are written. */\nconst EXTRA_HEADERS: Record<string, string> = {\n  'in-reply-to': 'In-Reply-To',\n  references: 'References',\n  'reply-to': 'Reply-To',\n  'list-unsubscribe': 'List-Unsubscribe',\n  'list-unsubscribe-post': 'List-Unsubscribe-Post',\n}\n\n/**\n * The one value RFC 8058 defines for `List-Unsubscribe-Post`, re-exported\n * from the module campaigns and sequences share (AGL-3307).\n */\nexport { LIST_UNSUBSCRIBE_ONE_CLICK }\n\nconst isAscii = (value: string) => isPrintableAscii(value)\n\n/** The address, validated and in its written form. */\nfunction normalizeAddress(input: OutreachMailAddressInput, field: string): OutreachMailAddress {\n  const record = typeof input === 'string' ? { address: input } : input\n  const address = String(record?.address ?? '').trim()\n  if (!address || address.length > 254 || !ADDRESS.test(address)) {\n    throw new Rfc5322MessageError('invalid-address', `The ${field} address is not a valid ASCII email address.`)\n  }\n  const name = typeof record?.name === 'string' ? record.name.trim() : ''\n  if (hasControlCharacter(name)) {\n    throw new Rfc5322MessageError('invalid-address', `The ${field} display name contains a control character.`)\n  }\n  return { address, name }\n}\n\n/**\n * RFC 2047 `B` encoded-words for a UTF-8 string, each at most 75 characters\n * and never splitting a character between two words.\n */\nexport function encodeRfc2047Words(value: string): string[] {\n  // 42 bytes base64-encode to 56 characters; with `=?UTF-8?B?` and `?=` a\n  // word is 68 — inside the 75 the RFC allows, and short enough that the\n  // first word still fits on a `Subject: ` line within 78 columns.\n  const maxBytes = 42\n  const words: string[] = []\n  let chunk = ''\n  let chunkBytes = 0\n  for (const character of value) {\n    const bytes = Buffer.byteLength(character, 'utf8')\n    if (chunkBytes + bytes > maxBytes && chunk) {\n      words.push(chunk)\n      chunk = ''\n      chunkBytes = 0\n    }\n    chunk += character\n    chunkBytes += bytes\n  }\n  if (chunk) words.push(chunk)\n  return words.map((word) => `=?UTF-8?B?${Buffer.from(word, 'utf8').toString('base64')}?=`)\n}\n\n/** A quoted-string, escaping the two characters RFC 5322 requires. */\nconst quoted = (value: string) => `\"${value.replace(/([\"\\\\])/g, '\\\\$1')}\"`\n\n/**\n * Whether ASCII text would read as an encoded-word to a mail client, which\n * decodes `=?…?=` wherever it appears in a header.\n */\nconst looksEncoded = (value: string) => /=\\?[^?]*\\?[bBqQ]\\?[^?]*\\?=/.test(value)\n\n/**\n * `Name <address>` as tokens to fold, the name quoted or encoded as it needs.\n * The angle-address is its own token, so a long name folds before it.\n */\nfunction formatAddress(address: OutreachMailAddress): string[] {\n  if (!address.name) return [address.address]\n  const name =\n    isAscii(address.name) && !looksEncoded(address.name)\n      ? [quoted(address.name)]\n      : encodeRfc2047Words(address.name)\n  return [...name, `<${address.address}>`]\n}\n\n/**\n * A value split at single spaces for folding, with every run of spaces kept:\n * an empty token is merged into the next one, so joining the tokens with one\n * space gives the value back exactly and no fold ever leaves a line of only\n * whitespace.\n */\nfunction spaceTokens(value: string): string[] {\n  const tokens: string[] = []\n  let pending = ''\n  for (const part of value.split(' ')) {\n    if (!part) {\n      pending += ' '\n      continue\n    }\n    tokens.push(`${pending}${part}`)\n    pending = ''\n  }\n  return tokens\n}\n\n/**\n * One header written as folded lines: `tokens` are joined by a space, and a\n * token that would push its line past 78 columns starts the next line.\n */\nfunction foldHeader(name: string, tokens: readonly string[]): string {\n  const lines: string[] = []\n  let line = `${name}:`\n  for (const token of tokens) {\n    if (line.length + 1 + token.length > FOLD_AT && line !== `${name}:`) {\n      lines.push(line)\n      line = ` ${token}`\n    } else {\n      line += ` ${token}`\n    }\n  }\n  lines.push(line)\n  for (const written of lines) {\n    if (written.length > MAX_LINE) {\n      throw new Rfc5322MessageError('invalid-header', `The ${name} header has a line longer than ${MAX_LINE} characters.`)\n    }\n  }\n  return lines.join(CRLF)\n}\n\n/** The subject, as words to fold: plain ASCII split on spaces, or encoded-words. */\nfunction subjectTokens(subject: string): string[] {\n  if (typeof subject !== 'string') {\n    throw new Rfc5322MessageError('invalid-subject', 'The subject must be text.')\n  }\n  if (hasControlCharacter(subject)) {\n    throw new Rfc5322MessageError('invalid-subject', 'The subject contains a line break or control character.')\n  }\n  const trimmed = subject.trim()\n  if (!trimmed) return []\n  if (isAscii(trimmed) && !looksEncoded(trimmed)) {\n    const words = spaceTokens(trimmed)\n    if (words.every((word) => `Subject: ${word}`.length <= MAX_LINE)) return words\n  }\n  return encodeRfc2047Words(trimmed)\n}\n\n/** RFC 5322 §3.3 date-time, in UTC. */\nexport function formatRfc5322Date(date: Date): string {\n  const days = ['Sun', 'Mon', 'Tue', 'Wed', 'Thu', 'Fri', 'Sat']\n  const months = ['Jan', 'Feb', 'Mar', 'Apr', 'May', 'Jun', 'Jul', 'Aug', 'Sep', 'Oct', 'Nov', 'Dec']\n  const pad = (value: number) => String(value).padStart(2, '0')\n  return (\n    `${days[date.getUTCDay()]}, ${pad(date.getUTCDate())} ${months[date.getUTCMonth()]} ` +\n    `${date.getUTCFullYear()} ${pad(date.getUTCHours())}:${pad(date.getUTCMinutes())}:` +\n    `${pad(date.getUTCSeconds())} +0000`\n  )\n}\n\n/** The extra headers, validated, named as written, in the order given. */\nfunction extraHeaders(headers: OutreachComposedMessage['headers']): Array<[string, string]> {\n  const written: Array<[string, string]> = []\n  const seen = new Set<string>()\n  for (const [rawName, rawValue] of Object.entries(headers ?? {})) {\n    if (rawValue === null || rawValue === undefined || rawValue === '') continue\n    const name = String(rawName).trim()\n    const lower = name.toLowerCase()\n    if (!FIELD_NAME.test(name)) {\n      throw new Rfc5322MessageError('invalid-header', 'A header name is not a valid field name.')\n    }\n    if (RESERVED_HEADERS.has(lower)) {\n      throw new Rfc5322MessageError('reserved-header', `The ${name} header is written by the message builder and cannot be set.`)\n    }\n    const canonical = EXTRA_HEADERS[lower] ?? (lower.startsWith('x-') ? name : null)\n    if (!canonical) {\n      throw new Rfc5322MessageError('unsupported-header', `The ${name} header is not one a sequence sends.`)\n    }\n    if (seen.has(lower)) {\n      throw new Rfc5322MessageError('invalid-header', `The ${name} header is given twice.`)\n    }\n    const value = String(rawValue).trim()\n    if (hasControlCharacter(value) || !isAscii(value)) {\n      throw new Rfc5322MessageError('invalid-header', `The ${name} header value must be printable ASCII on one line.`)\n    }\n    seen.add(lower)\n    written.push([canonical, value])\n  }\n  const post = written.find(([name]) => name === 'List-Unsubscribe-Post')\n  if (post) {\n    const unsubscribe = written.find(([name]) => name === 'List-Unsubscribe')\n    if (post[1] !== LIST_UNSUBSCRIBE_ONE_CLICK || !unsubscribe || !/<https:\\/\\/[^>]+>/.test(unsubscribe[1])) {\n      throw new Rfc5322MessageError(\n        'invalid-header',\n        `List-Unsubscribe-Post must be \"${LIST_UNSUBSCRIBE_ONE_CLICK}\" beside a List-Unsubscribe with an https address (RFC 8058).`,\n      )\n    }\n  }\n  return written\n}\n\n/** Line breaks of any kind, as CRLF, ending with one. */\nfunction canonicalBody(text: string): string {\n  const normalized = String(text ?? '').replace(/\\r\\n|\\r|\\n/g, CRLF)\n  return normalized.endsWith(CRLF) ? normalized : `${normalized}${CRLF}`\n}\n\n/**\n * RFC 2045 §6.7 quoted-printable for CRLF-separated text: `=`, non-ASCII\n * bytes and control characters as `=XX`, whitespace at a line's end encoded,\n * and soft breaks keeping every encoded line to 76 characters.\n */\nexport function encodeQuotedPrintable(text: string): string {\n  const hex = (byte: number) => `=${byte.toString(16).toUpperCase().padStart(2, '0')}`\n  return text\n    .split(CRLF)\n    .map((line) => {\n      const bytes = Buffer.from(line, 'utf8')\n      let encoded = ''\n      let current = ''\n      bytes.forEach((byte, index) => {\n        const last = index === bytes.length - 1\n        const literal =\n          (byte >= 33 && byte <= 126 && byte !== 61) || ((byte === 32 || byte === 9) && !last)\n        const token = literal ? String.fromCharCode(byte) : hex(byte)\n        if (current.length + token.length > 75) {\n          encoded += `${current}=${CRLF}`\n          current = ''\n        }\n        current += token\n      })\n      return encoded + current\n    })\n    .join(CRLF)\n}\n\n/** Whether the body can travel as 7bit: ASCII, and no line over 998 octets. */\nfunction isSevenBitSafe(body: string): boolean {\n  return body.split(CRLF).every((line) => isAscii(line) && line.length <= MAX_LINE)\n}\n\n/** Builds the message. Throws {@link Rfc5322MessageError} on anything unsafe. */\nexport function buildRfc5322Message(\n  message: OutreachComposedMessage,\n  options: BuildRfc5322Options = {},\n): BuiltRfc5322Message {\n  const from = normalizeAddress(message.from, 'From')\n  const to = normalizeAddress(message.to, 'To')\n  const subject = subjectTokens(message.subject)\n  const extras = extraHeaders(message.headers)\n\n  const domain = (options.messageIdDomain ?? from.address.slice(from.address.lastIndexOf('@') + 1)).trim()\n  const local = options.messageIdLocalPart ?? randomUUID()\n  if (!MESSAGE_ID_LOCAL.test(local) || !ADDRESS.test(`id@${domain}`)) {\n    throw new Rfc5322MessageError('invalid-message-id', 'The Message-ID would not be valid.')\n  }\n  const messageId = `<${local}@${domain}>`\n\n  const headers = [\n    foldHeader('From', formatAddress(from)),\n    foldHeader('To', formatAddress(to)),\n    ...(subject.length ? [foldHeader('Subject', subject)] : ['Subject:']),\n    `Date: ${formatRfc5322Date(options.date ?? new Date())}`,\n    `Message-ID: ${messageId}`,\n    ...extras.map(([name, value]) => foldHeader(name, spaceTokens(value))),\n    'MIME-Version: 1.0',\n  ]\n  const text = mimePart('text/plain', message.text)\n  const html = typeof message.html === 'string' && message.html.trim() ? mimePart('text/html', message.html) : null\n  if (!html) {\n    return {\n      raw: `${[...headers, ...text.headers].join(CRLF)}${CRLF}${CRLF}${text.body}`,\n      messageId,\n      subject: message.subject.trim(),\n    }\n  }\n  /*\n   * RFC 2046 §5.1.4: alternatives in increasing order of preference, so the\n   * plain text comes first and a client that can show HTML shows the HTML.\n   * The boundary is a UUID's characters behind a prefix, which no\n   * quoted-printable or 7bit body line can contain in full.\n   */\n  const boundary = options.boundary ?? `aglyn-alt-${randomUUID()}`\n  if (!/^[A-Za-z0-9'()+_,./:=?-]{1,70}$/.test(boundary)) {\n    throw new Rfc5322MessageError('invalid-header', 'The multipart boundary would not be valid.')\n  }\n  const part = (built: { headers: string[]; body: string }) =>\n    `--${boundary}${CRLF}${built.headers.join(CRLF)}${CRLF}${CRLF}${built.body}`\n  return {\n    raw:\n      `${[...headers, `Content-Type: multipart/alternative; boundary=\"${boundary}\"`].join(CRLF)}${CRLF}${CRLF}` +\n      `${part(text)}${part(html)}--${boundary}--${CRLF}`,\n    messageId,\n    subject: message.subject.trim(),\n  }\n}\n\n/**\n * One body with its content headers: `7bit` when it is ASCII with no line\n * over 998 octets, `quoted-printable` otherwise. The body ends with a CRLF,\n * which is what puts a following boundary on a line of its own.\n */\nfunction mimePart(type: 'text/plain' | 'text/html', content: string): { headers: string[]; body: string } {\n  const body = canonicalBody(content)\n  const sevenBit = isSevenBitSafe(body)\n  return {\n    headers: [\n      `Content-Type: ${type}; charset=UTF-8`,\n      `Content-Transfer-Encoding: ${sevenBit ? '7bit' : 'quoted-printable'}`,\n    ],\n    body: sevenBit ? body : encodeQuotedPrintable(body),\n  }\n}\n\n/** The `raw` field Gmail's `messages.send` takes: the message, base64url. */\nexport function encodeGmailRawMessage(raw: string): string {\n  return Buffer.from(raw, 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package/src/lib/transport/send-message.js

@@ -54,7 +54,7 @@ import { buildRfc5322Message, encodeGmailRawMessage } from "./rfc5322.js";
  * Answers the Gmail thread id, the `Message-ID` and the subject as sent,
  * which the runtime records on the enrollment for the next step to answer.
  */ export function sendComposedOutreachEmail(client, email, sender, options = {}) {
-    var _unsubscribe_ListUnsubscribe, _unsubscribe_ListUnsubscribePost, _email_threadId;
+    var _email_html, _unsubscribe_ListUnsubscribe, _unsubscribe_ListUnsubscribePost, _email_threadId;
     // The pair campaigns write too (AGL-3307): both URIs in one
     // `List-Unsubscribe`, and the one-click `Post` only beside the URL.
     const unsubscribe = listUnsubscribeHeaders({
@@ -66,6 +66,7 @@ import { buildRfc5322Message, encodeGmailRawMessage } from "./rfc5322.js";
         to: email.to,
         subject: email.subject,
         text: email.text,
+        html: (_email_html = email.html) != null ? _email_html : null,
         headers: {
             'In-Reply-To': email.inReplyTo,
             References: email.references,

package/src/lib/transport/send-message.js.map

@@ -1 +1 @@
-{"version":3,"sources":["../../../../../../../libs/plugins/outreach/src/lib/transport/send-message.ts"],"sourcesContent":["/**\n * @license\n * Copyright 2026 Aglyn LLC\n *\n * Licensed under the Apache License, Version 2.0 (the \"License\");\n * you may not use this file except in compliance with the License.\n * You may obtain a copy of the License at\n *\n *   http://www.apache.org/licenses/LICENSE-2.0\n *\n * Unless required by applicable law or agreed to in writing, software\n * distributed under the License is distributed on an \"AS IS\" BASIS,\n * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.\n * See the License for the specific language governing permissions and\n * limitations under the License.\n */\n\nimport type { ComposedOutreachEmail } from '../engine/compose'\nimport type { GmailClient } from './gmail-client'\nimport { listUnsubscribeHeaders } from '@aglyn/shared-util-email/list-unsubscribe'\nimport {\n  buildRfc5322Message,\n  encodeGmailRawMessage,\n  type OutreachComposedMessage,\n  type OutreachMailAddress,\n} from './rfc5322'\n\n/** What one sent message is known by afterwards. */\nexport interface OutreachSentMessage {\n  /** Gmail's id for the message in the sender's mailbox. */\n  gmailMessageId: string\n  /** Gmail's thread id — what the next step of the sequence replies into. */\n  threadId: string\n  /** The RFC 5322 `Message-ID` it carried, for `In-Reply-To`/`References`. */\n  messageId: string\n  /**\n   * The subject as sent — the thread's own subject when this message started\n   * the thread, which a later step answers with `Re:`.\n   */\n  subject: string\n}\n\nexport interface SendOutreachMessageOptions {\n  /** The Gmail thread to send into; a new thread when absent. */\n  threadId?: string | null\n  /** The `Date` header. Now when omitted. */\n  date?: Date\n  /** The Message-ID's domain. The From address's domain when omitted. */\n  messageIdDomain?: string\n  /**\n   * The Message-ID's local part, minted by the caller so it knows the id\n   * before the send answers (AGL-2981). A random one when omitted.\n   */\n  messageIdLocalPart?: string\n}\n\n/**\n * Builds a composed message and sends it through a mailbox's client\n * (AGL-2978). The one door a send goes through, so every Outreach message is\n * built by the same RFC 5322 writer and none can bypass its header checks.\n */\nexport async function sendOutreachMessage(\n  client: Pick<GmailClient, 'sendMessage'>,\n  message: OutreachComposedMessage,\n  options: SendOutreachMessageOptions = {},\n): Promise<OutreachSentMessage> {\n  const built = buildRfc5322Message(message, {\n    date: options.date,\n    messageIdDomain: options.messageIdDomain,\n    messageIdLocalPart: options.messageIdLocalPart,\n  })\n  const sent = await client.sendMessage({\n    raw: encodeGmailRawMessage(built.raw),\n    threadId: options.threadId ?? null,\n  })\n  return {\n    gmailMessageId: sent.id,\n    threadId: sent.threadId,\n    messageId: built.messageId,\n    subject: built.subject,\n  }\n}\n\n/**\n * Sends the email the engine composed (`composeOutreachEmail`) from a\n * mailbox, as the sending runtime does for a sequence step.\n *\n * The engine decides what is said and how it threads; this adds what the\n * engine leaves to the transport — the From line, from the mailbox's send-as\n * address and display name, and the MIME — and maps the rest onto headers:\n *\n * - a reply step goes into the engine's `threadId`, with its `In-Reply-To`\n *   and `References`;\n * - the unsubscribe URL and mailto become one `List-Unsubscribe`, and the\n *   URL adds `List-Unsubscribe-Post: List-Unsubscribe=One-Click` (RFC 8058).\n *\n * Answers the Gmail thread id, the `Message-ID` and the subject as sent,\n * which the runtime records on the enrollment for the next step to answer.\n */\nexport function sendComposedOutreachEmail(\n  client: Pick<GmailClient, 'sendMessage'>,\n  email: ComposedOutreachEmail,\n  sender: OutreachMailAddress,\n  options: Omit<SendOutreachMessageOptions, 'threadId'> = {},\n): Promise<OutreachSentMessage> {\n  // The pair campaigns write too (AGL-3307): both URIs in one\n  // `List-Unsubscribe`, and the one-click `Post` only beside the URL.\n  const unsubscribe = listUnsubscribeHeaders({\n    url: email.listUnsubscribeUrl,\n    mailto: email.listUnsubscribeMailto,\n  })\n  return sendOutreachMessage(\n    client,\n    {\n      from: sender,\n      to: email.to,\n      subject: email.subject,\n      text: email.text,\n      headers: {\n        'In-Reply-To': email.inReplyTo,\n        References: email.references,\n        'List-Unsubscribe': unsubscribe['List-Unsubscribe'] ?? null,\n        'List-Unsubscribe-Post': unsubscribe['List-Unsubscribe-Post'] ?? null,\n      },\n    },\n    { ...options, threadId: email.threadId ?? null },\n  )\n}\n"],"names":["listUnsubscribeHeaders","buildRfc5322Message","encodeGmailRawMessage","sendOutreachMessage","client","message","options","built","date","messageIdDomain","messageIdLocalPart","sent","sendMessage","raw","threadId","gmailMessageId","id","messageId","subject","sendComposedOutreachEmail","email","sender","unsubscribe","url","listUnsubscribeUrl","mailto","listUnsubscribeMailto","from","to","text","headers","inReplyTo","References","references"],"mappings":"AAAA;;;;;;;;;;;;;;;CAeC;AAID,SAASA,sBAAsB,QAAQ,4CAA2C;AAClF,SACEC,mBAAmB,EACnBC,qBAAqB,QAGhB,eAAW;AA+BlB;;;;CAIC,GACD,OAAO,eAAeC,oBACpBC,MAAwC,EACxCC,OAAgC,EAChCC,UAAsC,CAAC,CAAC;QAS5BA;IAPZ,MAAMC,QAAQN,oBAAoBI,SAAS;QACzCG,MAAMF,QAAQE,IAAI;QAClBC,iBAAiBH,QAAQG,eAAe;QACxCC,oBAAoBJ,QAAQI,kBAAkB;IAChD;IACA,MAAMC,OAAO,MAAMP,OAAOQ,WAAW,CAAC;QACpCC,KAAKX,sBAAsBK,MAAMM,GAAG;QACpCC,QAAQ,GAAER,oBAAAA,QAAQQ,QAAQ,YAAhBR,oBAAoB;IAChC;IACA,OAAO;QACLS,gBAAgBJ,KAAKK,EAAE;QACvBF,UAAUH,KAAKG,QAAQ;QACvBG,WAAWV,MAAMU,SAAS;QAC1BC,SAASX,MAAMW,OAAO;IACxB;AACF;AAEA;;;;;;;;;;;;;;;CAeC,GACD,OAAO,SAASC,0BACdf,MAAwC,EACxCgB,KAA4B,EAC5BC,MAA2B,EAC3Bf,UAAwD,CAAC,CAAC;QAkBhCgB,8BACKA,kCAGLF;IApB1B,4DAA4D;IAC5D,oEAAoE;IACpE,MAAME,cAActB,uBAAuB;QACzCuB,KAAKH,MAAMI,kBAAkB;QAC7BC,QAAQL,MAAMM,qBAAqB;IACrC;IACA,OAAOvB,oBACLC,QACA;QACEuB,MAAMN;QACNO,IAAIR,MAAMQ,EAAE;QACZV,SAASE,MAAMF,OAAO;QACtBW,MAAMT,MAAMS,IAAI;QAChBC,SAAS;YACP,eAAeV,MAAMW,SAAS;YAC9BC,YAAYZ,MAAMa,UAAU;YAC5B,kBAAkB,GAAEX,+BAAAA,WAAW,CAAC,mBAAmB,YAA/BA,+BAAmC;YACvD,uBAAuB,GAAEA,mCAAAA,WAAW,CAAC,wBAAwB,YAApCA,mCAAwC;QACnE;IACF,GACA,aAAKhB;QAASQ,QAAQ,GAAEM,kBAAAA,MAAMN,QAAQ,YAAdM,kBAAkB;;AAE9C"}
+{"version":3,"sources":["../../../../../../../libs/plugins/outreach/src/lib/transport/send-message.ts"],"sourcesContent":["/**\n * @license\n * Copyright 2026 Aglyn LLC\n *\n * Licensed under the Apache License, Version 2.0 (the \"License\");\n * you may not use this file except in compliance with the License.\n * You may obtain a copy of the License at\n *\n *   http://www.apache.org/licenses/LICENSE-2.0\n *\n * Unless required by applicable law or agreed to in writing, software\n * distributed under the License is distributed on an \"AS IS\" BASIS,\n * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.\n * See the License for the specific language governing permissions and\n * limitations under the License.\n */\n\nimport type { ComposedOutreachEmail } from '../engine/compose'\nimport type { GmailClient } from './gmail-client'\nimport { listUnsubscribeHeaders } from '@aglyn/shared-util-email/list-unsubscribe'\nimport {\n  buildRfc5322Message,\n  encodeGmailRawMessage,\n  type OutreachComposedMessage,\n  type OutreachMailAddress,\n} from './rfc5322'\n\n/** What one sent message is known by afterwards. */\nexport interface OutreachSentMessage {\n  /** Gmail's id for the message in the sender's mailbox. */\n  gmailMessageId: string\n  /** Gmail's thread id — what the next step of the sequence replies into. */\n  threadId: string\n  /** The RFC 5322 `Message-ID` it carried, for `In-Reply-To`/`References`. */\n  messageId: string\n  /**\n   * The subject as sent — the thread's own subject when this message started\n   * the thread, which a later step answers with `Re:`.\n   */\n  subject: string\n}\n\nexport interface SendOutreachMessageOptions {\n  /** The Gmail thread to send into; a new thread when absent. */\n  threadId?: string | null\n  /** The `Date` header. Now when omitted. */\n  date?: Date\n  /** The Message-ID's domain. The From address's domain when omitted. */\n  messageIdDomain?: string\n  /**\n   * The Message-ID's local part, minted by the caller so it knows the id\n   * before the send answers (AGL-2981). A random one when omitted.\n   */\n  messageIdLocalPart?: string\n}\n\n/**\n * Builds a composed message and sends it through a mailbox's client\n * (AGL-2978). The one door a send goes through, so every Outreach message is\n * built by the same RFC 5322 writer and none can bypass its header checks.\n */\nexport async function sendOutreachMessage(\n  client: Pick<GmailClient, 'sendMessage'>,\n  message: OutreachComposedMessage,\n  options: SendOutreachMessageOptions = {},\n): Promise<OutreachSentMessage> {\n  const built = buildRfc5322Message(message, {\n    date: options.date,\n    messageIdDomain: options.messageIdDomain,\n    messageIdLocalPart: options.messageIdLocalPart,\n  })\n  const sent = await client.sendMessage({\n    raw: encodeGmailRawMessage(built.raw),\n    threadId: options.threadId ?? null,\n  })\n  return {\n    gmailMessageId: sent.id,\n    threadId: sent.threadId,\n    messageId: built.messageId,\n    subject: built.subject,\n  }\n}\n\n/**\n * Sends the email the engine composed (`composeOutreachEmail`) from a\n * mailbox, as the sending runtime does for a sequence step.\n *\n * The engine decides what is said and how it threads; this adds what the\n * engine leaves to the transport — the From line, from the mailbox's send-as\n * address and display name, and the MIME — and maps the rest onto headers:\n *\n * - a reply step goes into the engine's `threadId`, with its `In-Reply-To`\n *   and `References`;\n * - the unsubscribe URL and mailto become one `List-Unsubscribe`, and the\n *   URL adds `List-Unsubscribe-Post: List-Unsubscribe=One-Click` (RFC 8058).\n *\n * Answers the Gmail thread id, the `Message-ID` and the subject as sent,\n * which the runtime records on the enrollment for the next step to answer.\n */\nexport function sendComposedOutreachEmail(\n  client: Pick<GmailClient, 'sendMessage'>,\n  email: ComposedOutreachEmail,\n  sender: OutreachMailAddress,\n  options: Omit<SendOutreachMessageOptions, 'threadId'> = {},\n): Promise<OutreachSentMessage> {\n  // The pair campaigns write too (AGL-3307): both URIs in one\n  // `List-Unsubscribe`, and the one-click `Post` only beside the URL.\n  const unsubscribe = listUnsubscribeHeaders({\n    url: email.listUnsubscribeUrl,\n    mailto: email.listUnsubscribeMailto,\n  })\n  return sendOutreachMessage(\n    client,\n    {\n      from: sender,\n      to: email.to,\n      subject: email.subject,\n      text: email.text,\n      html: email.html ?? null,\n      headers: {\n        'In-Reply-To': email.inReplyTo,\n        References: email.references,\n        'List-Unsubscribe': unsubscribe['List-Unsubscribe'] ?? null,\n        'List-Unsubscribe-Post': unsubscribe['List-Unsubscribe-Post'] ?? null,\n      },\n    },\n    { ...options, threadId: email.threadId ?? null },\n  )\n}\n"],"names":["listUnsubscribeHeaders","buildRfc5322Message","encodeGmailRawMessage","sendOutreachMessage","client","message","options","built","date","messageIdDomain","messageIdLocalPart","sent","sendMessage","raw","threadId","gmailMessageId","id","messageId","subject","sendComposedOutreachEmail","email","sender","unsubscribe","url","listUnsubscribeUrl","mailto","listUnsubscribeMailto","from","to","text","html","headers","inReplyTo","References","references"],"mappings":"AAAA;;;;;;;;;;;;;;;CAeC;AAID,SAASA,sBAAsB,QAAQ,4CAA2C;AAClF,SACEC,mBAAmB,EACnBC,qBAAqB,QAGhB,eAAW;AA+BlB;;;;CAIC,GACD,OAAO,eAAeC,oBACpBC,MAAwC,EACxCC,OAAgC,EAChCC,UAAsC,CAAC,CAAC;QAS5BA;IAPZ,MAAMC,QAAQN,oBAAoBI,SAAS;QACzCG,MAAMF,QAAQE,IAAI;QAClBC,iBAAiBH,QAAQG,eAAe;QACxCC,oBAAoBJ,QAAQI,kBAAkB;IAChD;IACA,MAAMC,OAAO,MAAMP,OAAOQ,WAAW,CAAC;QACpCC,KAAKX,sBAAsBK,MAAMM,GAAG;QACpCC,QAAQ,GAAER,oBAAAA,QAAQQ,QAAQ,YAAhBR,oBAAoB;IAChC;IACA,OAAO;QACLS,gBAAgBJ,KAAKK,EAAE;QACvBF,UAAUH,KAAKG,QAAQ;QACvBG,WAAWV,MAAMU,SAAS;QAC1BC,SAASX,MAAMW,OAAO;IACxB;AACF;AAEA;;;;;;;;;;;;;;;CAeC,GACD,OAAO,SAASC,0BACdf,MAAwC,EACxCgB,KAA4B,EAC5BC,MAA2B,EAC3Bf,UAAwD,CAAC,CAAC;QAehDc,aAIgBE,8BACKA,kCAGLF;IArB1B,4DAA4D;IAC5D,oEAAoE;IACpE,MAAME,cAActB,uBAAuB;QACzCuB,KAAKH,MAAMI,kBAAkB;QAC7BC,QAAQL,MAAMM,qBAAqB;IACrC;IACA,OAAOvB,oBACLC,QACA;QACEuB,MAAMN;QACNO,IAAIR,MAAMQ,EAAE;QACZV,SAASE,MAAMF,OAAO;QACtBW,MAAMT,MAAMS,IAAI;QAChBC,IAAI,GAAEV,cAAAA,MAAMU,IAAI,YAAVV,cAAc;QACpBW,SAAS;YACP,eAAeX,MAAMY,SAAS;YAC9BC,YAAYb,MAAMc,UAAU;YAC5B,kBAAkB,GAAEZ,+BAAAA,WAAW,CAAC,mBAAmB,YAA/BA,+BAAmC;YACvD,uBAAuB,GAAEA,mCAAAA,WAAW,CAAC,wBAAwB,YAApCA,mCAAwC;QACnE;IACF,GACA,aAAKhB;QAASQ,QAAQ,GAAEM,kBAAAA,MAAMN,QAAQ,YAAdM,kBAAkB;;AAE9C"}