@aglyn/plugins-outreach 1.0.0-beta.152 → 1.0.0-beta.154

package/src/lib/runtime/send-job.js.map

@@ -1 +1 @@
-{"version":3,"sources":["../../../../../../../libs/plugins/outreach/src/lib/runtime/send-job.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 { consentGroupForHost } from '@aglyn/aglyn/app-utils/consent-groups'\nimport { CRM_COLLECTIONS } from '@aglyn/aglyn/app-utils/crm'\nimport { normalizeCrmEmailTemplate } from '@aglyn/aglyn/app-utils/crm-email-templates'\nimport { randomUUID } from 'node:crypto'\nimport { composeOutreachEmail } from '../engine/compose'\nimport { planOutreachStepCompletion, type OutreachEnrollmentEvent } from '../engine/enrollment-state'\nimport { evaluateOutreachGates, type OutreachGateBlock, type OutreachGateLookups } from '../engine/gates'\nimport {\n  outreachSentToday,\n  outreachTickAllowance,\n  selectDueOutreachEnrollments,\n  type OutreachDueCandidate,\n} from '../engine/sending-capacity'\nimport { readOutreachEnrollCandidates, type OutreachEnrollCandidate } from '../enrollment/enroll-people'\nimport { readOutreachGateLookups } from '../enrollment/gate-lookups'\nimport { mailboxRef } from '../mailboxes/mailbox-credentials'\nimport { outreachEffectiveDailyCap, outreachLocalDay } from '../mailboxes/mailbox-settings'\nimport { markOutreachMailboxReconnectRequired, type OpenedOutreachMailbox } from '../mailboxes/mailbox-transport'\nimport { effectiveOutreachAllowedCountries } from '../model/compliance-settings'\nimport {\n  OUTREACH_COLLECTIONS,\n  type OutreachComplianceSettingsDocument,\n  type OutreachEnrollment,\n  type OutreachMailbox,\n  type OutreachSequence,\n  type OutreachStepRecord,\n  type OutreachTaskStep,\n} from '../model/outreach.types'\nimport { readOutreachComplianceSettingsDoc } from '../storage/compliance-settings-store'\nimport {\n  outreachOrgCollection,\n  readStoredOutreachEnrollment,\n  readStoredOutreachMailbox,\n  readStoredOutreachSequence,\n} from '../storage/outreach-records'\nimport { GmailTransportError, isReconnectRequired } from '../transport/gmail-errors'\nimport { Rfc5322MessageError } from '../transport/rfc5322'\nimport { sendComposedOutreachEmail } from '../transport/send-message'\nimport { applyOutreachEvent } from './enrollment-events'\nimport { outreachSendDigest, withRecentSend } from './mailbox-health-store'\nimport type { OutreachRuntimeDeps } from './runtime-deps'\nimport { fileOutreachEmail, fileOutreachTask, OUTREACH_TASK_KIND_TO_RECORD } from './timeline'\nimport { outreachUnsubscribeMailbox } from './unsubscribe-link'\n\n/*==========================================\n * THE SEND JOB (AGL-2981): every fifteen minutes, on the console.\n *\n * ## What comes due\n *\n * One collection-group read finds every active enrollment whose next step\n * is due, oldest first, bounded per run. They are grouped by workspace and\n * mailbox, and each group is judged before anything is sent:\n *\n * - the workspace: Outreach switched on, entitled and released to it;\n * - the mailbox: an enrollment whose mailbox is gone, disconnected, or whose\n *   member left the organization is STOPPED — nothing will ever send it, and\n *   leaving it active would show a sequence that is not running. A paused\n *   mailbox, or one waiting to be reconnected, holds its enrollments;\n * - the member it sends as: a lockdown of the platform, the workspace or the\n *   member holds everything.\n *\n * ## How much goes\n *\n * The engine's per-run allowance — the day's cap and ramp, spread across\n * the window, at most five a run — picks the enrollments (follow-ups first);\n * a task step is due whenever its time comes and spends no allowance.\n *\n * ## One send, exactly once\n *\n * Each email is CLAIMED before it is sent: a transaction over the enrollment\n * and its mailbox checks the enrollment is still active on the same step\n * with no live claim, and that the mailbox's day has room under its cap,\n * then writes the claim and reserves the day's count. Two runs racing for\n * one enrollment write one claim; two racing for one mailbox's last slot\n * reserve it once. The claim carries the `Message-ID` minted for the send,\n * so a claim a run died holding is settled by finding the message in the\n * mailbox rather than by sending it a second time. A send that fails hands\n * its reservation back.\n *\n * Before it is claimed, every gate is asked again — the do-not-contact\n * list, the suppression lists, the sales topic, the roster, the other\n * sequences — because a person enrolled on Monday can unsubscribe by\n * Thursday. A lookup that could not be made holds the send; a gate that\n * refuses stops the enrollment, saying why.\n *==========================================*/\n\nexport { OUTREACH_SEND_JOB_ID } from '../constants/runtime-jobs'\n\n/** The most due enrollments one run reads. */\nexport const OUTREACH_SEND_SCAN_LIMIT = 300\n\n/** How long a claim holds before a later run settles it. */\nexport const OUTREACH_CLAIM_STALE_MS = 10 * 60_000\n\n/** What one run did, for the tick's answer. */\nexport interface OutreachSendReport {\n  [key: string]: number\n  due: number\n  sent: number\n  tasks: number\n  /** Stopped by a gate or an unusable mailbox. */\n  stopped: number\n  /** Paused for the rep to fix, or failed for good. */\n  failed: number\n  /** Due, and left for a later run: the allowance, a lookup, a hold. */\n  held: number\n  /** Claims a dead run left, settled. */\n  recovered: number\n}\n\ntype Firestore = FirebaseFirestore.Firestore\n\ninterface MailboxRun {\n  orgId: string\n  org: Record<string, unknown>\n  mailbox: OutreachMailbox\n  settings: OutreachComplianceSettingsDocument\n  report: OutreachSendReport\n  deadlineMs: number\n  opened: OpenedOutreachMailbox | null\n  /** Set once the mailbox itself cannot send this run. */\n  stopped: boolean\n  templates: Map<string, string | null>\n}\n\nconst blankReport = (): OutreachSendReport => ({\n  due: 0,\n  sent: 0,\n  tasks: 0,\n  stopped: 0,\n  failed: 0,\n  held: 0,\n  recovered: 0,\n})\n\n/** Runs the send job once — see the module note. */\nexport async function runOutreachSendJob(\n  deps: OutreachRuntimeDeps,\n  context: { nowMs: number; deadlineMs: number },\n): Promise<OutreachSendReport> {\n  const firestore = deps.firestore()\n  const report = blankReport()\n  const due = await firestore\n    .collectionGroup(OUTREACH_COLLECTIONS.enrollments)\n    .where('status', '==', 'active')\n    .where('nextDueAtMs', '<=', context.nowMs)\n    .orderBy('nextDueAtMs')\n    .limit(OUTREACH_SEND_SCAN_LIMIT)\n    .get()\n  report.due = due.size\n  const byOrg = new Map<string, Map<string, OutreachEnrollment[]>>()\n  for (const doc of due.docs) {\n    const orgId = doc.ref.parent.parent?.id\n    const enrollment = readStoredOutreachEnrollment(doc.id, doc.data())\n    if (!orgId || !enrollment) continue\n    const mailboxes = byOrg.get(orgId) ?? new Map<string, OutreachEnrollment[]>()\n    mailboxes.set(enrollment.mailboxId, [...(mailboxes.get(enrollment.mailboxId) ?? []), enrollment])\n    byOrg.set(orgId, mailboxes)\n  }\n\n  for (const [orgId, mailboxes] of byOrg) {\n    const waiting = [...mailboxes.values()].reduce((sum, list) => sum + list.length, 0)\n    if (deps.now() >= context.deadlineMs) {\n      report.held += waiting\n      continue\n    }\n    const orgSnapshot = await firestore.collection('orgs').doc(orgId).get()\n    const org = (orgSnapshot.exists ? orgSnapshot.data() : null) as Record<string, unknown> | null\n    if (!org || (await deps.orgRefusal(orgId, org))) {\n      report.held += waiting\n      continue\n    }\n    const settings = await readOutreachComplianceSettingsDoc(firestore, orgId)\n    for (const [mailboxId, enrollments] of mailboxes) {\n      await runMailbox(deps, firestore, { orgId, org, mailboxId, enrollments, settings, report, context })\n    }\n  }\n  return report\n}\n\n/** The reason an unusable mailbox stops an enrollment, or `null` for a usable one. */\nasync function unusableMailbox(\n  firestore: Firestore,\n  orgId: string,\n  mailbox: OutreachMailbox | null,\n): Promise<string | null> {\n  if (!mailbox) return 'The mailbox this sequence sends from was removed.'\n  if (mailbox.status === 'disconnected') return 'The mailbox this sequence sends from was disconnected.'\n  const member = await firestore.collection('orgs').doc(orgId).collection('members').doc(mailbox.connectedByUid).get()\n  return member.exists\n    ? null\n    : 'The member who connected the mailbox this sequence sends from is no longer in the organization.'\n}\n\nasync function runMailbox(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  input: {\n    orgId: string\n    org: Record<string, unknown>\n    mailboxId: string\n    enrollments: OutreachEnrollment[]\n    settings: OutreachComplianceSettingsDocument\n    report: OutreachSendReport\n    context: { nowMs: number; deadlineMs: number }\n  },\n): Promise<void> {\n  const { orgId, org, report, context } = input\n  const nowMs = context.nowMs\n  const snapshot = await mailboxRef(firestore, orgId, input.mailboxId).get()\n  const mailbox = readStoredOutreachMailbox(input.mailboxId, snapshot.exists ? snapshot.data() : undefined)\n  const unusable = await unusableMailbox(firestore, orgId, mailbox)\n  if (unusable || !mailbox) {\n    for (const enrollment of input.enrollments) {\n      const outcome = await applyOutreachEvent(firestore, {\n        orgId,\n        enrollmentId: enrollment.id,\n        event: { type: 'stop', atMs: nowMs, byUid: null, reason: 'gate', detail: unusable },\n        nowMs,\n      })\n      if (outcome.changed) report.stopped += 1\n    }\n    return\n  }\n  if (mailbox.status !== 'connected' || (await deps.sendRefusal({ orgId, org, uid: mailbox.connectedByUid }))) {\n    report.held += input.enrollments.length\n    return\n  }\n\n  const run: MailboxRun = {\n    orgId,\n    org,\n    mailbox,\n    settings: input.settings,\n    report,\n    deadlineMs: context.deadlineMs,\n    opened: null,\n    stopped: false,\n    templates: new Map(),\n  }\n  const sequenceIds = [...new Set(input.enrollments.map((enrollment) => enrollment.sequenceId))]\n  const sequenceSnapshots = await firestore.getAll(\n    ...sequenceIds.map((id) => outreachOrgCollection(firestore, orgId, 'sequences').doc(id)),\n  )\n  const sequences = new Map<string, OutreachSequence>()\n  sequenceSnapshots.forEach((sequenceSnapshot, index) => {\n    const sequence = readStoredOutreachSequence(\n      sequenceIds[index],\n      sequenceSnapshot.exists ? sequenceSnapshot.data() : undefined,\n    )\n    if (sequence) sequences.set(sequence.id, sequence)\n  })\n\n  const candidates: OutreachDueCandidate[] = []\n  for (const enrollment of input.enrollments) {\n    const sequence = sequences.get(enrollment.sequenceId)\n    const claim = enrollment.sendClaim\n    if (claim && nowMs - claim.atMs < OUTREACH_CLAIM_STALE_MS) continue\n    if (claim && sequence) {\n      if (await recoverClaim(deps, firestore, run, enrollment, sequence)) report.recovered += 1\n      continue\n    }\n    if (sequence) candidates.push({ enrollment, sequence })\n  }\n\n  const allowance = outreachTickAllowance({ mailbox, nowMs })\n  const selection = selectDueOutreachEnrollments({ candidates, mailbox, nowMs, allowance: allowance.allowance })\n  report.held += selection.deferred.length\n\n  for (const candidate of selection.tasks) {\n    if (deps.now() >= context.deadlineMs) {\n      report.held += 1\n      continue\n    }\n    if (await runTaskStep(deps, firestore, run, candidate)) report.tasks += 1\n  }\n  if (!selection.emails.length) return\n\n  // The people behind the emails, read once per site: the contact and its\n  // company, and every lookup the gates decide on.\n  const people = new Map<string, OutreachEnrollCandidate>()\n  const lookups = new Map<string, OutreachGateLookups>()\n  const byHost = new Map<string, OutreachEnrollment[]>()\n  for (const candidate of selection.emails) {\n    const enrollment = candidate.enrollment as OutreachEnrollment\n    byHost.set(enrollment.hostId, [...(byHost.get(enrollment.hostId) ?? []), enrollment])\n  }\n  const siteNames = new Map<string, string>()\n  for (const [hostId, enrollments] of byHost) {\n    const contactGroupId = consentGroupForHost(org, hostId).groupId\n    const [candidatesRead, lookupsRead, host] = await Promise.all([\n      readOutreachEnrollCandidates(firestore, {\n        orgId,\n        hostId,\n        contactGroupId,\n        contactIds: enrollments.map((enrollment) => enrollment.contactId),\n      }),\n      readOutreachGateLookups(firestore, {\n        orgId,\n        hostId,\n        people: enrollments.map((enrollment) => ({ contactId: enrollment.contactId, email: enrollment.email })),\n      }),\n      firestore.collection('hosts').doc(hostId).get(),\n    ])\n    for (const person of candidatesRead) people.set(person.contactId, person)\n    for (const [contactId, answer] of lookupsRead) lookups.set(contactId, answer)\n    siteNames.set(hostId, host.exists ? String(host.get('name') ?? '') : '')\n  }\n\n  for (const candidate of selection.emails) {\n    if (run.stopped || deps.now() >= context.deadlineMs) {\n      report.held += 1\n      continue\n    }\n    const enrollment = candidate.enrollment as OutreachEnrollment\n    await runEmailStep(deps, firestore, run, {\n      enrollment,\n      sequence: candidate.sequence as OutreachSequence,\n      person: people.get(enrollment.contactId) ?? null,\n      lookups: lookups.get(enrollment.contactId) ?? null,\n      siteName: siteNames.get(enrollment.hostId) ?? '',\n    })\n  }\n}\n\n/** Any lookup the runtime could not make: the send waits for a run that can. */\nfunction uncheckable(lookups: OutreachGateLookups | null): boolean {\n  return !lookups || Object.values(lookups).some((value) => value === null)\n}\n\n/** The event a gate's refusal ends an enrollment with. */\nfunction gateEvent(blocks: readonly OutreachGateBlock[], atMs: number): OutreachEnrollmentEvent {\n  const optedOut = blocks.find((block) => block.code === 'do_not_contact' || block.code === 'sales_opted_out')\n  if (optedOut) return { type: 'opt_out', atMs, reason: 'do_not_contact', detail: optedOut.reason }\n  return { type: 'stop', atMs, byUid: null, reason: 'gate', detail: blocks.map((block) => block.reason).join(' ') }\n}\n\n/** The sender line a mailbox's mail goes out with. */\nconst senderOf = (mailbox: OutreachMailbox) => ({\n  address: mailbox.sendAs || mailbox.email,\n  name: mailbox.displayName || null,\n})\n\nasync function openClient(deps: OutreachRuntimeDeps, firestore: Firestore, run: MailboxRun) {\n  const opened = (run.opened ??= await deps.openMailbox(run.mailbox.id))\n  if (opened.ok === true) return opened.client\n  run.stopped = true\n  if (opened.reason !== 'not-configured') {\n    await markOutreachMailboxReconnectRequired(firestore, {\n      orgId: run.orgId,\n      mailboxId: run.mailbox.id,\n      errorCode: opened.reason,\n      nowMs: deps.now(),\n    })\n  }\n  return null\n}\n\n/**\n * Claims one step: the enrollment still active on the same step with no\n * live claim, and — for an email — a slot under the mailbox's cap today,\n * reserved in the same transaction.\n */\nasync function claimStep(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  enrollment: OutreachEnrollment,\n  messageId: string | null,\n): Promise<'claimed' | 'taken' | 'cap'> {\n  const enrollmentRef = outreachOrgCollection(firestore, run.orgId, 'enrollments').doc(enrollment.id)\n  const boxRef = mailboxRef(firestore, run.orgId, run.mailbox.id)\n  const nowMs = deps.now()\n  return firestore.runTransaction(async (transaction) => {\n    const [current, box] = await Promise.all([transaction.get(enrollmentRef), transaction.get(boxRef)])\n    const stored = readStoredOutreachEnrollment(enrollment.id, current.exists ? current.data() : undefined)\n    const claim = stored?.sendClaim\n    if (\n      !stored ||\n      stored.status !== 'active' ||\n      stored.stepIndex !== enrollment.stepIndex ||\n      stored.nextDueAtMs === null ||\n      stored.nextDueAtMs > nowMs ||\n      (claim && nowMs - claim.atMs < OUTREACH_CLAIM_STALE_MS)\n    ) {\n      return 'taken'\n    }\n    if (messageId) {\n      const mailbox = readStoredOutreachMailbox(run.mailbox.id, box.exists ? box.data() : undefined)\n      if (!mailbox || mailbox.status !== 'connected') return 'taken'\n      const sent = outreachSentToday(mailbox.health, nowMs, mailbox.timezone)\n      if (sent >= outreachEffectiveDailyCap(mailbox, nowMs)) return 'cap'\n      transaction.update(boxRef, {\n        'health.sentToday': sent + 1,\n        'health.sentOnDay': outreachLocalDay(nowMs, mailbox.timezone),\n      })\n    }\n    transaction.update(enrollmentRef, {\n      sendClaim: { token: randomUUID(), atMs: nowMs, stepIndex: enrollment.stepIndex, messageId },\n      updatedAtMs: nowMs,\n    })\n    return 'claimed'\n  })\n}\n\n/** Drops a claim, and hands an email's reservation back to the mailbox's day. */\nasync function releaseClaim(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  enrollment: Pick<OutreachEnrollment, 'id'>,\n  reserved: boolean,\n  event: OutreachEnrollmentEvent | null = null,\n): Promise<void> {\n  const nowMs = deps.now()\n  await applyOutreachEvent(firestore, {\n    orgId: run.orgId,\n    enrollmentId: enrollment.id,\n    event,\n    extra: () => ({ sendClaim: null }),\n    nowMs,\n  })\n  if (!reserved) return\n  const boxRef = mailboxRef(firestore, run.orgId, run.mailbox.id)\n  await firestore.runTransaction(async (transaction) => {\n    const box = await transaction.get(boxRef)\n    const mailbox = readStoredOutreachMailbox(run.mailbox.id, box.exists ? box.data() : undefined)\n    if (!mailbox || mailbox.health?.sentOnDay !== outreachLocalDay(nowMs, mailbox.timezone)) return\n    transaction.update(boxRef, { 'health.sentToday': Math.max(0, (Number(mailbox.health.sentToday) || 0) - 1) })\n  })\n}\n\n/**\n * Records a step that ran: the engine's completion patch, the claim\n * cleared, the step's record kept — and for an email the mailbox's send on\n * its day, its last-sent time and its window of recent sends. Refuses\n * (answers false) when the claim is no longer this run's.\n */\nasync function completeStep(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  input: {\n    enrollment: OutreachEnrollment\n    sequence: OutreachSequence\n    record: OutreachStepRecord\n    sent: { messageId: string; threadId: string; subject: string } | null\n    claimMessageId: string | null\n  },\n): Promise<boolean> {\n  const enrollmentRef = outreachOrgCollection(firestore, run.orgId, 'enrollments').doc(input.enrollment.id)\n  const boxRef = mailboxRef(firestore, run.orgId, run.mailbox.id)\n  const nowMs = deps.now()\n  return firestore.runTransaction(async (transaction) => {\n    const [current, box] = await Promise.all([\n      transaction.get(enrollmentRef),\n      input.sent ? transaction.get(boxRef) : Promise.resolve(null),\n    ])\n    const stored = readStoredOutreachEnrollment(input.enrollment.id, current.exists ? current.data() : undefined)\n    if (!stored?.sendClaim || stored.sendClaim.messageId !== input.claimMessageId) return false\n    if (stored.stepIndex !== input.enrollment.stepIndex) return false\n    // The step RAN, whatever happened to the enrollment while it did — a\n    // member paused it, a reply stopped it — so it is recorded as run, and a\n    // resume never sends it twice.\n    const plan = planOutreachStepCompletion({\n      enrollment: { ...stored, status: 'active' },\n      sequence: input.sequence,\n      mailbox: run.mailbox,\n      completedAtMs: nowMs,\n      sent: input.sent,\n      random: deps.random,\n    })\n    const patch: Record<string, unknown> = {\n      sendClaim: null,\n      stepRecords: [...(stored.stepRecords ?? []), input.record].slice(-20),\n      updatedAtMs: nowMs,\n      ...(plan.patch ?? {}),\n    }\n    if (stored.status !== 'active') {\n      patch['status'] = stored.status\n      if (stored.status !== 'paused') patch['nextDueAtMs'] = null\n    }\n    transaction.update(enrollmentRef, patch)\n    if (input.sent && box?.exists) {\n      const mailbox = readStoredOutreachMailbox(run.mailbox.id, box.data())\n      if (mailbox) {\n        const day = outreachLocalDay(nowMs, mailbox.timezone)\n        const counts = mailbox.health?.daily?.[day] ?? { sent: 0, bounces: 0, replies: 0 }\n        transaction.update(boxRef, {\n          'health.lastSentAtMs': nowMs,\n          'health.lastErrorAtMs': null,\n          'health.lastErrorCode': null,\n          [`health.daily.${day}`]: { ...counts, sent: (Number(counts.sent) || 0) + 1 },\n          'health.recentSends': withRecentSend(mailbox.health?.recentSends, {\n            id: outreachSendDigest(input.sent.messageId),\n            atMs: nowMs,\n            bounced: false,\n          }),\n          updatedAtMs: nowMs,\n        })\n      }\n    }\n    return true\n  })\n}\n\n/** One task step: the rep's task on the contact, then the step recorded. */\nasync function runTaskStep(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  candidate: OutreachDueCandidate,\n): Promise<boolean> {\n  const enrollment = candidate.enrollment as OutreachEnrollment\n  const sequence = candidate.sequence as OutreachSequence\n  const step = sequence.steps[enrollment.stepIndex] as OutreachTaskStep\n  if ((await claimStep(deps, firestore, run, enrollment, null)) !== 'claimed') return false\n  const nowMs = deps.now()\n  let taskId: string | null\n  try {\n    const written = await fileOutreachTask(deps, {\n      orgId: run.orgId,\n      hostId: enrollment.hostId,\n      contactId: enrollment.contactId,\n      dedupeKey: `step:${enrollment.id}:${step.id}`,\n      title: step.title,\n      notes: `From sequence step ${enrollment.stepIndex + 1}.`,\n      kind: OUTREACH_TASK_KIND_TO_RECORD[step.taskKind] ?? 'todo',\n      dueAtMs: nowMs,\n      assigneeUid: run.mailbox.connectedByUid,\n    })\n    taskId = written?.ok ? written.id : null\n    if (written?.ok === false) console.warn(`[outreach] a task step's task was not filed: ${written.error}`)\n  } catch (error) {\n    // The record system failed rather than refused: the step waits for a\n    // run that can file its task.\n    console.error('[outreach] filing a task step failed; the step waits', error)\n    await releaseClaim(deps, firestore, run, enrollment, false)\n    return false\n  }\n  return completeStep(deps, firestore, run, {\n    enrollment,\n    sequence,\n    record: { stepIndex: enrollment.stepIndex, stepId: step.id, kind: 'task', atMs: nowMs, taskId },\n    sent: null,\n    claimMessageId: null,\n  })\n}\n\n/** A CRM template's body, read once per run. */\nasync function templateBody(firestore: Firestore, run: MailboxRun, templateId: string): Promise<string | null> {\n  if (!run.templates.has(templateId)) {\n    const snapshot = await firestore\n      .collection('orgs')\n      .doc(run.orgId)\n      .collection(CRM_COLLECTIONS.emailTemplates)\n      .doc(templateId)\n      .get()\n    run.templates.set(\n      templateId,\n      snapshot.exists ? normalizeCrmEmailTemplate(snapshot.data() as Record<string, unknown>).body : null,\n    )\n  }\n  return run.templates.get(templateId) ?? null\n}\n\nasync function runEmailStep(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  input: {\n    enrollment: OutreachEnrollment\n    sequence: OutreachSequence\n    person: OutreachEnrollCandidate | null\n    lookups: OutreachGateLookups | null\n    siteName: string\n  },\n): Promise<void> {\n  const { enrollment, sequence, person } = input\n  const { report, mailbox } = run\n  const nowMs = deps.now()\n  const stop = async (event: OutreachEnrollmentEvent, counter: 'stopped' | 'failed') => {\n    const outcome = await applyOutreachEvent(firestore, { orgId: run.orgId, enrollmentId: enrollment.id, event, nowMs })\n    if (outcome.changed) report[counter] += 1\n  }\n\n  // Every gate again, on the person as they stand now.\n  if (!person?.contact) {\n    return stop({ type: 'stop', atMs: nowMs, byUid: null, reason: 'gate', detail: 'This contact no longer exists in the CRM.' }, 'stopped')\n  }\n  if (!person.visible) {\n    return stop(\n      { type: 'stop', atMs: nowMs, byUid: null, reason: 'gate', detail: \"This contact is no longer in the sequence's site's CRM.\" },\n      'stopped',\n    )\n  }\n  if (uncheckable(input.lookups)) {\n    report.held += 1\n    return\n  }\n  const contactGroupId = consentGroupForHost(run.org, enrollment.hostId).groupId\n  const gate = evaluateOutreachGates({\n    email: enrollment.email,\n    contact: person.contact,\n    contactGroupId,\n    company: person.company,\n    settings: {\n      ...sequence.settings,\n      allowedCountries: effectiveOutreachAllowedCountries(\n        sequence.settings.allowedCountries,\n        run.settings.allowedCountries,\n      ),\n    },\n    personalLine: enrollment.personalLine,\n    attestations: enrollment.attestations,\n    enrollmentId: enrollment.id,\n    lookups: input.lookups as OutreachGateLookups,\n  })\n  if (!gate.allowed) return stop(gateEvent(gate.blocks, nowMs), 'stopped')\n\n  // The email, with its way out.\n  const listUnsubscribeUrl = deps.unsubscribeUrl({ orgId: run.orgId, enrollmentId: enrollment.id })\n  const mailto = outreachUnsubscribeMailbox(mailbox.email)\n  if (!listUnsubscribeUrl || !mailto) {\n    // No link can be minted — no secret, or no HTTPS console origin — and an\n    // email without its one-click way out does not leave.\n    console.error('[outreach] no unsubscribe link could be minted; nothing sends until one can')\n    run.stopped = true\n    report.held += 1\n    return\n  }\n  const step = sequence.steps[enrollment.stepIndex]\n  const sender = senderOf(mailbox)\n  const composed = composeOutreachEmail({\n    sequence,\n    enrollment,\n    orgSettings: run.settings,\n    merge: {\n      contact: person.contact,\n      contactGroupId,\n      sender: { name: mailbox.displayName, email: sender.address },\n      site: { name: input.siteName },\n    },\n    templateBody: step?.kind === 'email' && step.templateId ? await templateBody(firestore, run, step.templateId) : null,\n    listUnsubscribeUrl,\n    listUnsubscribeMailto: mailto.uri,\n  })\n  if (composed.error || !composed.email) {\n    const code = composed.error?.code\n    if (code === 'missing_postal_address' || code === 'missing_legal_name') {\n      // The organization's footer: nothing of theirs sends until it is set.\n      run.stopped = true\n      report.held += 1\n      return\n    }\n    if (code === 'invalid_recipient' || code === 'missing_thread' || code === 'not_an_email_step') {\n      return stop({ type: 'send_failed', atMs: nowMs, detail: composed.error?.message }, 'failed')\n    }\n    // The sequence's own words: the rep fixes the step and resumes.\n    return stop({ type: 'pause', atMs: nowMs, byUid: null, detail: composed.error?.message }, 'failed')\n  }\n  if (composed.unresolvedFields.length) {\n    const fields = composed.unresolvedFields.map((field) => `{{${field}}}`).join(', ')\n    return stop(\n      {\n        type: 'pause',\n        atMs: nowMs,\n        byUid: null,\n        detail: `Paused before sending: this contact has nothing for ${fields}. Fill it in and resume.`,\n      },\n      'failed',\n    )\n  }\n\n  // Claimed, then sent, then recorded.\n  const domain = sender.address.slice(sender.address.lastIndexOf('@') + 1)\n  const local = randomUUID()\n  const messageId = `<${local}@${domain}>`\n  const claimed = await claimStep(deps, firestore, run, enrollment, messageId)\n  if (claimed !== 'claimed') {\n    if (claimed === 'cap') run.stopped = true\n    report.held += 1\n    return\n  }\n  const client = await openClient(deps, firestore, run)\n  if (!client) {\n    await releaseClaim(deps, firestore, run, enrollment, true)\n    report.held += 1\n    return\n  }\n  let sent: Awaited<ReturnType<typeof sendComposedOutreachEmail>>\n  try {\n    sent = await sendComposedOutreachEmail(client, composed.email, sender, {\n      messageIdLocalPart: local,\n      messageIdDomain: domain,\n    })\n  } catch (error) {\n    if (error instanceof Rfc5322MessageError || (error instanceof GmailTransportError && error.code === 'invalid_request')) {\n      await releaseClaim(deps, firestore, run, enrollment, true, {\n        type: 'send_failed',\n        atMs: deps.now(),\n        detail: `Gmail refused the email: ${error.message}`,\n      })\n      report.failed += 1\n      return\n    }\n    await releaseClaim(deps, firestore, run, enrollment, true)\n    report.held += 1\n    run.stopped = true\n    const code = error instanceof GmailTransportError ? error.code : 'unexpected'\n    if (isReconnectRequired(error)) {\n      await markOutreachMailboxReconnectRequired(firestore, {\n        orgId: run.orgId,\n        mailboxId: mailbox.id,\n        errorCode: code,\n        nowMs: deps.now(),\n      })\n    } else {\n      await mailboxRef(firestore, run.orgId, mailbox.id)\n        .update({ 'health.lastErrorAtMs': deps.now(), 'health.lastErrorCode': code })\n        .catch(() => undefined)\n    }\n    console.error(`[outreach] a send from a mailbox failed (${code}); its sends wait for the next run`)\n    return\n  }\n\n  const record: OutreachStepRecord = {\n    stepIndex: enrollment.stepIndex,\n    stepId: step?.id ?? '',\n    kind: 'email',\n    atMs: deps.now(),\n    gmailMessageId: sent.gmailMessageId,\n    gmailThreadId: sent.threadId,\n    messageId: sent.messageId,\n    subject: sent.subject,\n  }\n  await completeStep(deps, firestore, run, {\n    enrollment,\n    sequence,\n    record,\n    sent: { messageId: sent.messageId, threadId: sent.threadId, subject: sent.subject },\n    claimMessageId: messageId,\n  })\n  report.sent += 1\n  await fileOutreachEmail(deps, {\n    orgId: run.orgId,\n    hostId: enrollment.hostId,\n    contactId: enrollment.contactId,\n    direction: 'outbound',\n    subject: sent.subject,\n    from: sender.address,\n    to: composed.email.to,\n    messageId: sent.messageId,\n    inReplyTo: composed.email.inReplyTo ?? null,\n    body: composed.email.text,\n    atMs: record.atMs,\n    byUid: mailbox.connectedByUid,\n    byName: mailbox.displayName || null,\n  })\n}\n\n/**\n * Settles a claim a run died holding. A task step's claim is dropped and\n * the step runs again (its task is filed once however often it is asked).\n * An email's claim looks for the message it minted in the mailbox: found,\n * the send happened and is recorded; not found, it did not, and the claim\n * and its reservation are handed back for the next run.\n */\nasync function recoverClaim(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  enrollment: OutreachEnrollment,\n  sequence: OutreachSequence,\n): Promise<boolean> {\n  const claim = enrollment.sendClaim\n  if (!claim) return false\n  if (!claim.messageId) {\n    await releaseClaim(deps, firestore, run, enrollment, false)\n    return true\n  }\n  const client = await openClient(deps, firestore, run)\n  if (!client) return false\n  const bare = claim.messageId.replace(/^<|>$/g, '')\n  const found = await client.listMessages({ q: `rfc822msgid:${bare}`, maxResults: 1, includeSpamTrash: true })\n  const hit = found.messages[0]\n  if (!hit) {\n    await releaseClaim(deps, firestore, run, enrollment, true)\n    return true\n  }\n  const message = await client.getMessage(hit.id, { metadataHeaders: ['Subject'] })\n  const subject = message.headers.find((header) => header.name.toLowerCase() === 'subject')?.value ?? ''\n  const step = sequence.steps[enrollment.stepIndex]\n  return completeStep(deps, firestore, run, {\n    enrollment,\n    sequence,\n    record: {\n      stepIndex: enrollment.stepIndex,\n      stepId: step?.id ?? 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+{"version":3,"sources":["../../../../../../../libs/plugins/outreach/src/lib/runtime/send-job.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 { consentGroupForHost } from '@aglyn/aglyn/app-utils/consent-groups'\nimport { CRM_COLLECTIONS } from '@aglyn/aglyn/app-utils/crm'\nimport { normalizeCrmEmailTemplate } from '@aglyn/aglyn/app-utils/crm-email-templates'\nimport { randomUUID } from 'node:crypto'\nimport { composeOutreachEmail } from '../engine/compose'\nimport { planOutreachStepCompletion, type OutreachEnrollmentEvent } from '../engine/enrollment-state'\nimport { evaluateOutreachGates, type OutreachGateBlock, type OutreachGateLookups } from '../engine/gates'\nimport {\n  outreachSentToday,\n  outreachTickAllowance,\n  selectDueOutreachEnrollments,\n  type OutreachDueCandidate,\n} from '../engine/sending-capacity'\nimport { readOutreachEnrollCandidates, type OutreachEnrollCandidate } from '../enrollment/enroll-people'\nimport { readOutreachGateLookups } from '../enrollment/gate-lookups'\nimport { mailboxRef } from '../mailboxes/mailbox-credentials'\nimport { outreachEffectiveDailyCap, outreachLocalDay } from '../mailboxes/mailbox-settings'\nimport { markOutreachMailboxReconnectRequired, type OpenedOutreachMailbox } from '../mailboxes/mailbox-transport'\nimport { effectiveOutreachAllowedCountries } from '../model/compliance-settings'\nimport {\n  OUTREACH_COLLECTIONS,\n  type OutreachComplianceSettingsDocument,\n  type OutreachEnrollment,\n  type OutreachMailbox,\n  type OutreachSequence,\n  type OutreachStepRecord,\n  type OutreachTaskStep,\n} from '../model/outreach.types'\nimport { readOutreachComplianceSettingsDoc } from '../storage/compliance-settings-store'\nimport {\n  outreachEnrollmentLink,\n  outreachEnrollmentPerson,\n  outreachOrgCollection,\n  readStoredOutreachEnrollment,\n  readStoredOutreachMailbox,\n  readStoredOutreachSequence,\n} from '../storage/outreach-records'\nimport { GmailTransportError, isReconnectRequired } from '../transport/gmail-errors'\nimport { Rfc5322MessageError } from '../transport/rfc5322'\nimport { sendComposedOutreachEmail } from '../transport/send-message'\nimport { applyOutreachEvent } from './enrollment-events'\nimport { outreachSendDigest, withRecentSend } from './mailbox-health-store'\nimport type { OutreachRuntimeDeps } from './runtime-deps'\nimport { fileOutreachEmail, fileOutreachTask, OUTREACH_TASK_KIND_TO_RECORD } from './timeline'\nimport { outreachUnsubscribeMailbox } from './unsubscribe-link'\n\n/*==========================================\n * THE SEND JOB (AGL-2981): every fifteen minutes, on the console.\n *\n * ## What comes due\n *\n * One collection-group read finds every active enrollment whose next step\n * is due, oldest first, bounded per run. They are grouped by workspace and\n * mailbox, and each group is judged before anything is sent:\n *\n * - the workspace: Outreach switched on, entitled and released to it;\n * - the mailbox: an enrollment whose mailbox is gone, disconnected, or whose\n *   member left the organization is STOPPED — nothing will ever send it, and\n *   leaving it active would show a sequence that is not running. A paused\n *   mailbox, or one waiting to be reconnected, holds its enrollments;\n * - the member it sends as: a lockdown of the platform, the workspace or the\n *   member holds everything.\n *\n * ## How much goes\n *\n * The engine's per-run allowance — the day's cap and ramp, spread across\n * the window, at most five a run — picks the enrollments (follow-ups first);\n * a task step is due whenever its time comes and spends no allowance.\n *\n * ## One send, exactly once\n *\n * Each email is CLAIMED before it is sent: a transaction over the enrollment\n * and its mailbox checks the enrollment is still active on the same step\n * with no live claim, and that the mailbox's day has room under its cap,\n * then writes the claim and reserves the day's count. Two runs racing for\n * one enrollment write one claim; two racing for one mailbox's last slot\n * reserve it once. The claim carries the `Message-ID` minted for the send,\n * so a claim a run died holding is settled by finding the message in the\n * mailbox rather than by sending it a second time. A send that fails hands\n * its reservation back.\n *\n * Before it is claimed, every gate is asked again — the do-not-contact\n * list, the suppression lists, the sales topic, the roster, the other\n * sequences — because a person enrolled on Monday can unsubscribe by\n * Thursday. A lookup that could not be made holds the send; a gate that\n * refuses stops the enrollment, saying why.\n *==========================================*/\n\nexport { OUTREACH_SEND_JOB_ID } from '../constants/runtime-jobs'\n\n/** The most due enrollments one run reads. */\nexport const OUTREACH_SEND_SCAN_LIMIT = 300\n\n/** How long a claim holds before a later run settles it. */\nexport const OUTREACH_CLAIM_STALE_MS = 10 * 60_000\n\n/** What one run did, for the tick's answer. */\nexport interface OutreachSendReport {\n  [key: string]: number\n  due: number\n  sent: number\n  tasks: number\n  /** Stopped by a gate or an unusable mailbox. */\n  stopped: number\n  /** Paused for the rep to fix, or failed for good. */\n  failed: number\n  /** Due, and left for a later run: the allowance, a lookup, a hold. */\n  held: number\n  /** Claims a dead run left, settled. */\n  recovered: number\n}\n\ntype Firestore = FirebaseFirestore.Firestore\n\ninterface MailboxRun {\n  orgId: string\n  org: Record<string, unknown>\n  mailbox: OutreachMailbox\n  settings: OutreachComplianceSettingsDocument\n  report: OutreachSendReport\n  deadlineMs: number\n  opened: OpenedOutreachMailbox | null\n  /** Set once the mailbox itself cannot send this run. */\n  stopped: boolean\n  templates: Map<string, string | null>\n}\n\nconst blankReport = (): OutreachSendReport => ({\n  due: 0,\n  sent: 0,\n  tasks: 0,\n  stopped: 0,\n  failed: 0,\n  held: 0,\n  recovered: 0,\n})\n\n/** Runs the send job once — see the module note. */\nexport async function runOutreachSendJob(\n  deps: OutreachRuntimeDeps,\n  context: { nowMs: number; deadlineMs: number },\n): Promise<OutreachSendReport> {\n  const firestore = deps.firestore()\n  const report = blankReport()\n  const due = await firestore\n    .collectionGroup(OUTREACH_COLLECTIONS.enrollments)\n    .where('status', '==', 'active')\n    .where('nextDueAtMs', '<=', context.nowMs)\n    .orderBy('nextDueAtMs')\n    .limit(OUTREACH_SEND_SCAN_LIMIT)\n    .get()\n  report.due = due.size\n  const byOrg = new Map<string, Map<string, OutreachEnrollment[]>>()\n  for (const doc of due.docs) {\n    const orgId = doc.ref.parent.parent?.id\n    const enrollment = readStoredOutreachEnrollment(doc.id, doc.data())\n    if (!orgId || !enrollment) continue\n    const mailboxes = byOrg.get(orgId) ?? new Map<string, OutreachEnrollment[]>()\n    mailboxes.set(enrollment.mailboxId, [...(mailboxes.get(enrollment.mailboxId) ?? []), enrollment])\n    byOrg.set(orgId, mailboxes)\n  }\n\n  for (const [orgId, mailboxes] of byOrg) {\n    const waiting = [...mailboxes.values()].reduce((sum, list) => sum + list.length, 0)\n    if (deps.now() >= context.deadlineMs) {\n      report.held += waiting\n      continue\n    }\n    const orgSnapshot = await firestore.collection('orgs').doc(orgId).get()\n    const org = (orgSnapshot.exists ? orgSnapshot.data() : null) as Record<string, unknown> | null\n    if (!org || (await deps.orgRefusal(orgId, org))) {\n      report.held += waiting\n      continue\n    }\n    const settings = await readOutreachComplianceSettingsDoc(firestore, orgId)\n    for (const [mailboxId, enrollments] of mailboxes) {\n      await runMailbox(deps, firestore, { orgId, org, mailboxId, enrollments, settings, report, context })\n    }\n  }\n  return report\n}\n\n/** The reason an unusable mailbox stops an enrollment, or `null` for a usable one. */\nasync function unusableMailbox(\n  firestore: Firestore,\n  orgId: string,\n  mailbox: OutreachMailbox | null,\n): Promise<string | null> {\n  if (!mailbox) return 'The mailbox this sequence sends from was removed.'\n  if (mailbox.status === 'disconnected') return 'The mailbox this sequence sends from was disconnected.'\n  const member = await firestore.collection('orgs').doc(orgId).collection('members').doc(mailbox.connectedByUid).get()\n  return member.exists\n    ? null\n    : 'The member who connected the mailbox this sequence sends from is no longer in the organization.'\n}\n\nasync function runMailbox(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  input: {\n    orgId: string\n    org: Record<string, unknown>\n    mailboxId: string\n    enrollments: OutreachEnrollment[]\n    settings: OutreachComplianceSettingsDocument\n    report: OutreachSendReport\n    context: { nowMs: number; deadlineMs: number }\n  },\n): Promise<void> {\n  const { orgId, org, report, context } = input\n  const nowMs = context.nowMs\n  const snapshot = await mailboxRef(firestore, orgId, input.mailboxId).get()\n  const mailbox = readStoredOutreachMailbox(input.mailboxId, snapshot.exists ? snapshot.data() : undefined)\n  const unusable = await unusableMailbox(firestore, orgId, mailbox)\n  if (unusable || !mailbox) {\n    for (const enrollment of input.enrollments) {\n      const outcome = await applyOutreachEvent(firestore, {\n        orgId,\n        enrollmentId: enrollment.id,\n        event: { type: 'stop', atMs: nowMs, byUid: null, reason: 'gate', detail: unusable },\n        nowMs,\n      })\n      if (outcome.changed) report.stopped += 1\n    }\n    return\n  }\n  if (mailbox.status !== 'connected' || (await deps.sendRefusal({ orgId, org, uid: mailbox.connectedByUid }))) {\n    report.held += input.enrollments.length\n    return\n  }\n\n  const run: MailboxRun = {\n    orgId,\n    org,\n    mailbox,\n    settings: input.settings,\n    report,\n    deadlineMs: context.deadlineMs,\n    opened: null,\n    stopped: false,\n    templates: new Map(),\n  }\n  const sequenceIds = [...new Set(input.enrollments.map((enrollment) => enrollment.sequenceId))]\n  const sequenceSnapshots = await firestore.getAll(\n    ...sequenceIds.map((id) => outreachOrgCollection(firestore, orgId, 'sequences').doc(id)),\n  )\n  const sequences = new Map<string, OutreachSequence>()\n  sequenceSnapshots.forEach((sequenceSnapshot, index) => {\n    const sequence = readStoredOutreachSequence(\n      sequenceIds[index],\n      sequenceSnapshot.exists ? sequenceSnapshot.data() : undefined,\n    )\n    if (sequence) sequences.set(sequence.id, sequence)\n  })\n\n  const candidates: OutreachDueCandidate[] = []\n  for (const enrollment of input.enrollments) {\n    const sequence = sequences.get(enrollment.sequenceId)\n    const claim = enrollment.sendClaim\n    if (claim && nowMs - claim.atMs < OUTREACH_CLAIM_STALE_MS) continue\n    if (claim && sequence) {\n      if (await recoverClaim(deps, firestore, run, enrollment, sequence)) report.recovered += 1\n      continue\n    }\n    if (sequence) candidates.push({ enrollment, sequence })\n  }\n\n  const allowance = outreachTickAllowance({ mailbox, nowMs })\n  const selection = selectDueOutreachEnrollments({ candidates, mailbox, nowMs, allowance: allowance.allowance })\n  report.held += selection.deferred.length\n\n  for (const candidate of selection.tasks) {\n    if (deps.now() >= context.deadlineMs) {\n      report.held += 1\n      continue\n    }\n    if (await runTaskStep(deps, firestore, run, candidate)) report.tasks += 1\n  }\n  if (!selection.emails.length) return\n\n  // The people behind the emails, read once per site: the contact and its\n  // company, and every lookup the gates decide on.\n  const people = new Map<string, OutreachEnrollCandidate>()\n  const lookups = new Map<string, OutreachGateLookups>()\n  const byHost = new Map<string, OutreachEnrollment[]>()\n  for (const candidate of selection.emails) {\n    const enrollment = candidate.enrollment as OutreachEnrollment\n    byHost.set(enrollment.hostId, [...(byHost.get(enrollment.hostId) ?? []), enrollment])\n  }\n  const siteNames = new Map<string, string>()\n  for (const [hostId, enrollments] of byHost) {\n    const contactGroupId = consentGroupForHost(org, hostId).groupId\n    // Each by the record it names — the contact, or the lead while the\n    // person is one (AGL-3234) — keyed by that record's id.\n    const [candidatesRead, lookupsRead, host] = await Promise.all([\n      readOutreachEnrollCandidates(firestore, {\n        orgId,\n        hostId,\n        contactGroupId,\n        people: enrollments.map(outreachEnrollmentPerson),\n      }),\n      readOutreachGateLookups(firestore, {\n        orgId,\n        hostId,\n        people: enrollments.map((enrollment) => {\n          const person = outreachEnrollmentPerson(enrollment)\n          return {\n            personId: person.id,\n            contactId: person.kind === 'contact' ? person.id : null,\n            leadId: person.kind === 'lead' ? person.id : null,\n            email: enrollment.email,\n          }\n        }),\n      }),\n      firestore.collection('hosts').doc(hostId).get(),\n    ])\n    for (const person of candidatesRead) people.set(person.personId, person)\n    for (const [personId, answer] of lookupsRead) lookups.set(personId, answer)\n    siteNames.set(hostId, host.exists ? String(host.get('name') ?? '') : '')\n  }\n\n  for (const candidate of selection.emails) {\n    if (run.stopped || deps.now() >= context.deadlineMs) {\n      report.held += 1\n      continue\n    }\n    const enrollment = candidate.enrollment as OutreachEnrollment\n    const personId = outreachEnrollmentPerson(enrollment).id\n    await runEmailStep(deps, firestore, run, {\n      enrollment,\n      sequence: candidate.sequence as OutreachSequence,\n      person: people.get(personId) ?? null,\n      lookups: lookups.get(personId) ?? null,\n      siteName: siteNames.get(enrollment.hostId) ?? '',\n    })\n  }\n}\n\n/** Any lookup the runtime could not make: the send waits for a run that can. */\nfunction uncheckable(lookups: OutreachGateLookups | null): boolean {\n  return !lookups || Object.values(lookups).some((value) => value === null)\n}\n\n/** The event a gate's refusal ends an enrollment with. */\nfunction gateEvent(blocks: readonly OutreachGateBlock[], atMs: number): OutreachEnrollmentEvent {\n  const optedOut = blocks.find((block) => block.code === 'do_not_contact' || block.code === 'sales_opted_out')\n  if (optedOut) return { type: 'opt_out', atMs, reason: 'do_not_contact', detail: optedOut.reason }\n  return { type: 'stop', atMs, byUid: null, reason: 'gate', detail: blocks.map((block) => block.reason).join(' ') }\n}\n\n/** The sender line a mailbox's mail goes out with. */\nconst senderOf = (mailbox: OutreachMailbox) => ({\n  address: mailbox.sendAs || mailbox.email,\n  name: mailbox.displayName || null,\n})\n\nasync function openClient(deps: OutreachRuntimeDeps, firestore: Firestore, run: MailboxRun) {\n  const opened = (run.opened ??= await deps.openMailbox(run.mailbox.id))\n  if (opened.ok === true) return opened.client\n  run.stopped = true\n  if (opened.reason !== 'not-configured') {\n    await markOutreachMailboxReconnectRequired(firestore, {\n      orgId: run.orgId,\n      mailboxId: run.mailbox.id,\n      errorCode: opened.reason,\n      nowMs: deps.now(),\n    })\n  }\n  return null\n}\n\n/**\n * Claims one step: the enrollment still active on the same step with no\n * live claim, and — for an email — a slot under the mailbox's cap today,\n * reserved in the same transaction.\n */\nasync function claimStep(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  enrollment: OutreachEnrollment,\n  messageId: string | null,\n): Promise<'claimed' | 'taken' | 'cap'> {\n  const enrollmentRef = outreachOrgCollection(firestore, run.orgId, 'enrollments').doc(enrollment.id)\n  const boxRef = mailboxRef(firestore, run.orgId, run.mailbox.id)\n  const nowMs = deps.now()\n  return firestore.runTransaction(async (transaction) => {\n    const [current, box] = await Promise.all([transaction.get(enrollmentRef), transaction.get(boxRef)])\n    const stored = readStoredOutreachEnrollment(enrollment.id, current.exists ? current.data() : undefined)\n    const claim = stored?.sendClaim\n    if (\n      !stored ||\n      stored.status !== 'active' ||\n      stored.stepIndex !== enrollment.stepIndex ||\n      stored.nextDueAtMs === null ||\n      stored.nextDueAtMs > nowMs ||\n      (claim && nowMs - claim.atMs < OUTREACH_CLAIM_STALE_MS)\n    ) {\n      return 'taken'\n    }\n    if (messageId) {\n      const mailbox = readStoredOutreachMailbox(run.mailbox.id, box.exists ? box.data() : undefined)\n      if (!mailbox || mailbox.status !== 'connected') return 'taken'\n      const sent = outreachSentToday(mailbox.health, nowMs, mailbox.timezone)\n      if (sent >= outreachEffectiveDailyCap(mailbox, nowMs)) return 'cap'\n      transaction.update(boxRef, {\n        'health.sentToday': sent + 1,\n        'health.sentOnDay': outreachLocalDay(nowMs, mailbox.timezone),\n      })\n    }\n    transaction.update(enrollmentRef, {\n      sendClaim: { token: randomUUID(), atMs: nowMs, stepIndex: enrollment.stepIndex, messageId },\n      updatedAtMs: nowMs,\n    })\n    return 'claimed'\n  })\n}\n\n/** Drops a claim, and hands an email's reservation back to the mailbox's day. */\nasync function releaseClaim(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  enrollment: Pick<OutreachEnrollment, 'id'>,\n  reserved: boolean,\n  event: OutreachEnrollmentEvent | null = null,\n): Promise<void> {\n  const nowMs = deps.now()\n  await applyOutreachEvent(firestore, {\n    orgId: run.orgId,\n    enrollmentId: enrollment.id,\n    event,\n    extra: () => ({ sendClaim: null }),\n    nowMs,\n  })\n  if (!reserved) return\n  const boxRef = mailboxRef(firestore, run.orgId, run.mailbox.id)\n  await firestore.runTransaction(async (transaction) => {\n    const box = await transaction.get(boxRef)\n    const mailbox = readStoredOutreachMailbox(run.mailbox.id, box.exists ? box.data() : undefined)\n    if (!mailbox || mailbox.health?.sentOnDay !== outreachLocalDay(nowMs, mailbox.timezone)) return\n    transaction.update(boxRef, { 'health.sentToday': Math.max(0, (Number(mailbox.health.sentToday) || 0) - 1) })\n  })\n}\n\n/**\n * Records a step that ran: the engine's completion patch, the claim\n * cleared, the step's record kept — and for an email the mailbox's send on\n * its day, its last-sent time and its window of recent sends. Refuses\n * (answers false) when the claim is no longer this run's.\n */\nasync function completeStep(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  input: {\n    enrollment: OutreachEnrollment\n    sequence: OutreachSequence\n    record: OutreachStepRecord\n    sent: { messageId: string; threadId: string; subject: string } | null\n    claimMessageId: string | null\n  },\n): Promise<boolean> {\n  const enrollmentRef = outreachOrgCollection(firestore, run.orgId, 'enrollments').doc(input.enrollment.id)\n  const boxRef = mailboxRef(firestore, run.orgId, run.mailbox.id)\n  const nowMs = deps.now()\n  return firestore.runTransaction(async (transaction) => {\n    const [current, box] = await Promise.all([\n      transaction.get(enrollmentRef),\n      input.sent ? transaction.get(boxRef) : Promise.resolve(null),\n    ])\n    const stored = readStoredOutreachEnrollment(input.enrollment.id, current.exists ? current.data() : undefined)\n    if (!stored?.sendClaim || stored.sendClaim.messageId !== input.claimMessageId) return false\n    if (stored.stepIndex !== input.enrollment.stepIndex) return false\n    // The step RAN, whatever happened to the enrollment while it did — a\n    // member paused it, a reply stopped it — so it is recorded as run, and a\n    // resume never sends it twice.\n    const plan = planOutreachStepCompletion({\n      enrollment: { ...stored, status: 'active' },\n      sequence: input.sequence,\n      mailbox: run.mailbox,\n      completedAtMs: nowMs,\n      sent: input.sent,\n      random: deps.random,\n    })\n    const patch: Record<string, unknown> = {\n      sendClaim: null,\n      stepRecords: [...(stored.stepRecords ?? []), input.record].slice(-20),\n      updatedAtMs: nowMs,\n      ...(plan.patch ?? {}),\n    }\n    if (stored.status !== 'active') {\n      patch['status'] = stored.status\n      if (stored.status !== 'paused') patch['nextDueAtMs'] = null\n    }\n    transaction.update(enrollmentRef, patch)\n    if (input.sent && box?.exists) {\n      const mailbox = readStoredOutreachMailbox(run.mailbox.id, box.data())\n      if (mailbox) {\n        const day = outreachLocalDay(nowMs, mailbox.timezone)\n        const counts = mailbox.health?.daily?.[day] ?? { sent: 0, bounces: 0, replies: 0 }\n        transaction.update(boxRef, {\n          'health.lastSentAtMs': nowMs,\n          'health.lastErrorAtMs': null,\n          'health.lastErrorCode': null,\n          [`health.daily.${day}`]: { ...counts, sent: (Number(counts.sent) || 0) + 1 },\n          'health.recentSends': withRecentSend(mailbox.health?.recentSends, {\n            id: outreachSendDigest(input.sent.messageId),\n            atMs: nowMs,\n            bounced: false,\n          }),\n          updatedAtMs: nowMs,\n        })\n      }\n    }\n    return true\n  })\n}\n\n/** One task step: the rep's task on the contact, then the step recorded. */\nasync function runTaskStep(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  candidate: OutreachDueCandidate,\n): Promise<boolean> {\n  const enrollment = candidate.enrollment as OutreachEnrollment\n  const sequence = candidate.sequence as OutreachSequence\n  const step = sequence.steps[enrollment.stepIndex] as OutreachTaskStep\n  if ((await claimStep(deps, firestore, run, enrollment, null)) !== 'claimed') return false\n  const nowMs = deps.now()\n  let taskId: string | null\n  try {\n    const written = await fileOutreachTask(deps, {\n      orgId: run.orgId,\n      hostId: enrollment.hostId,\n      link: outreachEnrollmentLink(enrollment),\n      dedupeKey: `step:${enrollment.id}:${step.id}`,\n      title: step.title,\n      notes: `From sequence step ${enrollment.stepIndex + 1}.`,\n      kind: OUTREACH_TASK_KIND_TO_RECORD[step.taskKind] ?? 'todo',\n      dueAtMs: nowMs,\n      assigneeUid: run.mailbox.connectedByUid,\n    })\n    taskId = written?.ok ? written.id : null\n    if (written?.ok === false) console.warn(`[outreach] a task step's task was not filed: ${written.error}`)\n  } catch (error) {\n    // The record system failed rather than refused: the step waits for a\n    // run that can file its task.\n    console.error('[outreach] filing a task step failed; the step waits', error)\n    await releaseClaim(deps, firestore, run, enrollment, false)\n    return false\n  }\n  return completeStep(deps, firestore, run, {\n    enrollment,\n    sequence,\n    record: { stepIndex: enrollment.stepIndex, stepId: step.id, kind: 'task', atMs: nowMs, taskId },\n    sent: null,\n    claimMessageId: null,\n  })\n}\n\n/** A CRM template's body, read once per run. */\nasync function templateBody(firestore: Firestore, run: MailboxRun, templateId: string): Promise<string | null> {\n  if (!run.templates.has(templateId)) {\n    const snapshot = await firestore\n      .collection('orgs')\n      .doc(run.orgId)\n      .collection(CRM_COLLECTIONS.emailTemplates)\n      .doc(templateId)\n      .get()\n    run.templates.set(\n      templateId,\n      snapshot.exists ? normalizeCrmEmailTemplate(snapshot.data() as Record<string, unknown>).body : null,\n    )\n  }\n  return run.templates.get(templateId) ?? null\n}\n\nasync function runEmailStep(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  input: {\n    enrollment: OutreachEnrollment\n    sequence: OutreachSequence\n    person: OutreachEnrollCandidate | null\n    lookups: OutreachGateLookups | null\n    siteName: string\n  },\n): Promise<void> {\n  const { enrollment, sequence, person } = input\n  const { report, mailbox } = run\n  const nowMs = deps.now()\n  const stop = async (event: OutreachEnrollmentEvent, counter: 'stopped' | 'failed') => {\n    const outcome = await applyOutreachEvent(firestore, { orgId: run.orgId, enrollmentId: enrollment.id, event, nowMs })\n    if (outcome.changed) report[counter] += 1\n  }\n\n  // Every gate again, on the person as they stand now.\n  if (!person?.contact) {\n    return stop(\n      {\n        type: 'stop',\n        atMs: nowMs,\n        byUid: null,\n        reason: 'gate',\n        detail:\n          enrollment.target === 'lead'\n            ? \"This lead no longer exists in the sequence's site's CRM.\"\n            : 'This contact no longer exists in the CRM.',\n      },\n      'stopped',\n    )\n  }\n  if (person.convertedContactId && enrollment.target === 'lead') {\n    // The lead converted and the enrollment has not followed it yet: the\n    // conversion's listener re-points it, and the next run sends as the contact.\n    report.held += 1\n    return\n  }\n  if (!person.visible) {\n    return stop(\n      { type: 'stop', atMs: nowMs, byUid: null, reason: 'gate', detail: \"This contact is no longer in the sequence's site's CRM.\" },\n      'stopped',\n    )\n  }\n  if (uncheckable(input.lookups)) {\n    report.held += 1\n    return\n  }\n  const contactGroupId = consentGroupForHost(run.org, enrollment.hostId).groupId\n  const gate = evaluateOutreachGates({\n    email: enrollment.email,\n    contact: person.contact,\n    contactGroupId,\n    company: person.company,\n    settings: {\n      ...sequence.settings,\n      allowedCountries: effectiveOutreachAllowedCountries(\n        sequence.settings.allowedCountries,\n        run.settings.allowedCountries,\n      ),\n    },\n    personalLine: enrollment.personalLine,\n    attestations: enrollment.attestations,\n    enrollmentId: enrollment.id,\n    lookups: input.lookups as OutreachGateLookups,\n  })\n  if (!gate.allowed) return stop(gateEvent(gate.blocks, nowMs), 'stopped')\n\n  // The email, with its way out.\n  const listUnsubscribeUrl = deps.unsubscribeUrl({ orgId: run.orgId, enrollmentId: enrollment.id })\n  const mailto = outreachUnsubscribeMailbox(mailbox.email)\n  if (!listUnsubscribeUrl || !mailto) {\n    // No link can be minted — no secret, or no HTTPS console origin — and an\n    // email without its one-click way out does not leave.\n    console.error('[outreach] no unsubscribe link could be minted; nothing sends until one can')\n    run.stopped = true\n    report.held += 1\n    return\n  }\n  const step = sequence.steps[enrollment.stepIndex]\n  const sender = senderOf(mailbox)\n  const composed = composeOutreachEmail({\n    sequence,\n    enrollment,\n    orgSettings: run.settings,\n    merge: {\n      // For a lead, the contact-shaped view of it (`leadAsContact`), so a\n      // step written with `{{contact.*}}` reads the lead; `{{lead.*}}` reads\n      // the lead's own document beside it.\n      contact: person.contact,\n      contactGroupId,\n      lead: person.lead,\n      sender: { name: mailbox.displayName, email: sender.address },\n      site: { name: input.siteName },\n    },\n    templateBody: step?.kind === 'email' && step.templateId ? await templateBody(firestore, run, step.templateId) : null,\n    listUnsubscribeUrl,\n    listUnsubscribeMailto: mailto.uri,\n  })\n  if (composed.error || !composed.email) {\n    const code = composed.error?.code\n    if (code === 'missing_postal_address' || code === 'missing_legal_name') {\n      // The organization's footer: nothing of theirs sends until it is set.\n      run.stopped = true\n      report.held += 1\n      return\n    }\n    if (code === 'invalid_recipient' || code === 'missing_thread' || code === 'not_an_email_step') {\n      return stop({ type: 'send_failed', atMs: nowMs, detail: composed.error?.message }, 'failed')\n    }\n    // The sequence's own words: the rep fixes the step and resumes.\n    return stop({ type: 'pause', atMs: nowMs, byUid: null, detail: composed.error?.message }, 'failed')\n  }\n  if (composed.unresolvedFields.length) {\n    const fields = composed.unresolvedFields.map((field) => `{{${field}}}`).join(', ')\n    return stop(\n      {\n        type: 'pause',\n        atMs: nowMs,\n        byUid: null,\n        detail: `Paused before sending: this contact has nothing for ${fields}. Fill it in and resume.`,\n      },\n      'failed',\n    )\n  }\n\n  // Claimed, then sent, then recorded.\n  const domain = sender.address.slice(sender.address.lastIndexOf('@') + 1)\n  const local = randomUUID()\n  const messageId = `<${local}@${domain}>`\n  const claimed = await claimStep(deps, firestore, run, enrollment, messageId)\n  if (claimed !== 'claimed') {\n    if (claimed === 'cap') run.stopped = true\n    report.held += 1\n    return\n  }\n  const client = await openClient(deps, firestore, run)\n  if (!client) {\n    await releaseClaim(deps, firestore, run, enrollment, true)\n    report.held += 1\n    return\n  }\n  let sent: Awaited<ReturnType<typeof sendComposedOutreachEmail>>\n  try {\n    sent = await sendComposedOutreachEmail(client, composed.email, sender, {\n      messageIdLocalPart: local,\n      messageIdDomain: domain,\n    })\n  } catch (error) {\n    if (error instanceof Rfc5322MessageError || (error instanceof GmailTransportError && error.code === 'invalid_request')) {\n      await releaseClaim(deps, firestore, run, enrollment, true, {\n        type: 'send_failed',\n        atMs: deps.now(),\n        detail: `Gmail refused the email: ${error.message}`,\n      })\n      report.failed += 1\n      return\n    }\n    await releaseClaim(deps, firestore, run, enrollment, true)\n    report.held += 1\n    run.stopped = true\n    const code = error instanceof GmailTransportError ? error.code : 'unexpected'\n    if (isReconnectRequired(error)) {\n      await markOutreachMailboxReconnectRequired(firestore, {\n        orgId: run.orgId,\n        mailboxId: mailbox.id,\n        errorCode: code,\n        nowMs: deps.now(),\n      })\n    } else {\n      await mailboxRef(firestore, run.orgId, mailbox.id)\n        .update({ 'health.lastErrorAtMs': deps.now(), 'health.lastErrorCode': code })\n        .catch(() => undefined)\n    }\n    console.error(`[outreach] a send from a mailbox failed (${code}); its sends wait for the next run`)\n    return\n  }\n\n  const record: OutreachStepRecord = {\n    stepIndex: enrollment.stepIndex,\n    stepId: step?.id ?? '',\n    kind: 'email',\n    atMs: deps.now(),\n    gmailMessageId: sent.gmailMessageId,\n    gmailThreadId: sent.threadId,\n    messageId: sent.messageId,\n    subject: sent.subject,\n  }\n  await completeStep(deps, firestore, run, {\n    enrollment,\n    sequence,\n    record,\n    sent: { messageId: sent.messageId, threadId: sent.threadId, subject: sent.subject },\n    claimMessageId: messageId,\n  })\n  report.sent += 1\n  await fileOutreachEmail(deps, {\n    orgId: run.orgId,\n    hostId: enrollment.hostId,\n    link: outreachEnrollmentLink(enrollment),\n    direction: 'outbound',\n    subject: sent.subject,\n    from: sender.address,\n    to: composed.email.to,\n    messageId: sent.messageId,\n    inReplyTo: composed.email.inReplyTo ?? null,\n    body: composed.email.text,\n    atMs: record.atMs,\n    byUid: mailbox.connectedByUid,\n    byName: mailbox.displayName || null,\n  })\n}\n\n/**\n * Settles a claim a run died holding. A task step's claim is dropped and\n * the step runs again (its task is filed once however often it is asked).\n * An email's claim looks for the message it minted in the mailbox: found,\n * the send happened and is recorded; not found, it did not, and the claim\n * and its reservation are handed back for the next run.\n */\nasync function recoverClaim(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  run: MailboxRun,\n  enrollment: OutreachEnrollment,\n  sequence: OutreachSequence,\n): Promise<boolean> {\n  const claim = enrollment.sendClaim\n  if (!claim) return false\n  if (!claim.messageId) {\n    await releaseClaim(deps, firestore, run, enrollment, false)\n    return true\n  }\n  const client = await openClient(deps, firestore, run)\n  if (!client) return false\n  const bare = claim.messageId.replace(/^<|>$/g, '')\n  const found = await client.listMessages({ q: `rfc822msgid:${bare}`, maxResults: 1, includeSpamTrash: true })\n  const hit = found.messages[0]\n  if (!hit) {\n    await releaseClaim(deps, firestore, run, enrollment, true)\n    return true\n  }\n  const message = await client.getMessage(hit.id, { metadataHeaders: ['Subject'] })\n  const subject = message.headers.find((header) => header.name.toLowerCase() === 'subject')?.value ?? ''\n  const step = sequence.steps[enrollment.stepIndex]\n  return completeStep(deps, firestore, run, {\n    enrollment,\n    sequence,\n    record: {\n      stepIndex: enrollment.stepIndex,\n      stepId: step?.id ?? 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package/src/lib/runtime/sync-job.js

@@ -24,10 +24,11 @@ import { mailboxRef } from "../mailboxes/mailbox-credentials.js";
 import { markOutreachMailboxReconnectRequired } from "../mailboxes/mailbox-transport.js";
 import { OUTREACH_COLLECTIONS } from "../model/outreach.types.js";
 import { addOutreachDoNotContact } from "../storage/do-not-contact-store.js";
-import { outreachOrgCollection, readStoredOutreachEnrollment, readStoredOutreachMailbox, readStoredOutreachSequence } from "../storage/outreach-records.js";
+import { outreachEnrollmentLink, outreachOrgCollection, readStoredOutreachEnrollment, readStoredOutreachMailbox, readStoredOutreachSequence } from "../storage/outreach-records.js";
 import { GmailTransportError, isReconnectRequired } from "../transport/gmail-errors.js";
 import { applyOutreachEvent, recordOutreachOptOut } from "./enrollment-events.js";
 import { applyOutreachMailboxHealth, emptyOutreachHealthDelta } from "./mailbox-health-store.js";
+import { markOutreachLeadWorking } from "./lead-records.js";
 import { fileOutreachEmail, fileOutreachTask } from "./timeline.js";
 import { outreachUnsubscribeMailbox } from "./unsubscribe-link.js";
 /*==========================================
@@ -310,7 +311,7 @@ async function syncMailbox(deps, firestore, input) {
     await fileOutreachEmail(context.deps, {
         orgId: context.orgId,
         hostId: enrollment.hostId,
-        contactId: enrollment.contactId,
+        link: outreachEnrollmentLink(enrollment),
         direction: 'inbound',
         subject: message.subject,
         from: (_emailAddressOf = emailAddressOf(message.from)) != null ? _emailAddressOf : message.from,
@@ -388,7 +389,7 @@ async function syncMailbox(deps, firestore, input) {
                         await fileOutreachTask(deps, {
                             orgId: context.orgId,
                             hostId: enrollment.hostId,
-                            contactId: enrollment.contactId,
+                            link: outreachEnrollmentLink(enrollment),
                             dedupeKey: `reply:${(_messageIdOf = messageIdOf(decidingMessage)) != null ? _messageIdOf : decidingMessage.id}`,
                             title: `Reply from ${enrollment.contactName || enrollment.email}`,
                             notes: crmInboundExcerpt((_ref2 = (_decidingMessage_textBody = decidingMessage.textBody) != null ? _decidingMessage_textBody : decidingMessage.snippet) != null ? _ref2 : '', (_decidingMessage_htmlBody = decidingMessage.htmlBody) != null ? _decidingMessage_htmlBody : '').slice(0, 500),
@@ -400,6 +401,13 @@ async function syncMailbox(deps, firestore, input) {
                         console.error('[outreach] the reply task could not be filed', error);
                     }
                 }
+                // A lead somebody wrote back to is being worked (AGL-3234).
+                if (enrollment.target === 'lead' && enrollment.leadId) {
+                    await markOutreachLeadWorking(firestore, {
+                        hostId: enrollment.hostId,
+                        leadId: enrollment.leadId
+                    });
+                }
                 context.delta.replies += 1;
                 event = {
                     type: 'reply',

package/src/lib/runtime/sync-job.js.map

@@ -1 +1 @@
-{"version":3,"sources":["../../../../../../../libs/plugins/outreach/src/lib/runtime/sync-job.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 { normalizeContactEmail } from '@aglyn/aglyn/app-utils/contacts'\nimport { crmInboundExcerpt, emailAddressOf } from '@aglyn/aglyn/app-utils/crm-inbound'\nimport { outreachMessageIdHeader } from '../engine/compose'\nimport { readOutreachDeliveryReport } from '../engine/delivery-status'\nimport type { OutreachEnrollmentEvent } from '../engine/enrollment-state'\nimport { effectiveOutreachWindow, postponeOutreachForAutoReply } from '../engine/schedule'\nimport {\n  decideOutreachThread,\n  type OutreachMessageClassification,\n  type OutreachThreadDecision,\n} from '../engine/thread-classification'\nimport { outreachHeader, outreachThreadMessageFromGmail, type OutreachThreadMessage } from '../engine/thread-message'\nimport { mailboxRef } from '../mailboxes/mailbox-credentials'\nimport { markOutreachMailboxReconnectRequired } from '../mailboxes/mailbox-transport'\nimport {\n  OUTREACH_COLLECTIONS,\n  type OutreachEnrollment,\n  type OutreachMailbox,\n  type OutreachSequence,\n} from '../model/outreach.types'\nimport { addOutreachDoNotContact } from '../storage/do-not-contact-store'\nimport {\n  outreachOrgCollection,\n  readStoredOutreachEnrollment,\n  readStoredOutreachMailbox,\n  readStoredOutreachSequence,\n} from '../storage/outreach-records'\nimport type { GmailClient } from '../transport/gmail-client'\nimport { GmailTransportError, isReconnectRequired } from '../transport/gmail-errors'\nimport { applyOutreachEvent, recordOutreachOptOut } from './enrollment-events'\nimport {\n  applyOutreachMailboxHealth,\n  emptyOutreachHealthDelta,\n  type OutreachMailboxHealthDelta,\n} from './mailbox-health-store'\nimport type { OutreachRuntimeDeps } from './runtime-deps'\nimport { fileOutreachEmail, fileOutreachTask } from './timeline'\nimport { outreachUnsubscribeMailbox } from './unsubscribe-link'\n\n/*==========================================\n * THE SYNC JOB (AGL-2981): every fifteen minutes, on the console.\n *\n * For each connected or paused mailbox, what came back since the last run —\n * read with `format=full`, turned into the engine's message shape and\n * classified by `decideOutreachThread`:\n *\n * - a REPLY stops the enrollment, files the message on the contact's\n *   timeline (once per `Message-ID`, under the capture address's own id for\n *   it) and gives the rep the task \"Reply from <name>\";\n * - an OUT-OF-OFFICE postpones the next step a working week from the reply;\n * - an OPT-OUT — a reply asking to be left alone, or a message to the\n *   `+unsubscribe` address the `mailto:` names — puts the address on the\n *   organization's do-not-contact list and off the site's `sales` topic,\n *   and stops every open enrollment of it;\n * - a HARD BOUNCE stops the enrollment, files the address on the platform's\n *   suppression list and the do-not-contact list.\n *\n * Four reads find those, each narrowed by Gmail rather than read in full:\n * the threads of this mailbox's enrollments that have new mail; delivery\n * reports outside those threads (a receiving server's own bounce), by\n * searching for the mail systems that send them; messages to the\n * unsubscribe address; and messages from the people this mailbox is\n * writing to, in a thread of their own.\n *\n * Every write it makes is idempotent — the do-not-contact list keeps its\n * first entry, a topic opt-out keeps its first moment, a timeline entry is\n * filed once per message — and the messages it handled are marked AFTER\n * their effects, on the enrollment and on the mailbox, so a run that dies\n * part-way repeats harmless work rather than skipping some. The mailbox's\n * health takes the run's bounces and complaints in one write at the end,\n * which is where it pauses itself.\n *==========================================*/\n\nexport { OUTREACH_SYNC_JOB_ID } from '../constants/runtime-jobs'\n\n/** The furthest back a run reads: a mailbox's first run, or one that fell behind. */\nexport const OUTREACH_SYNC_LOOKBACK_MS = 7 * 24 * 60 * 60_000\n\n/** How far a run reads back past the previous one, for mail Gmail indexed late. */\nexport const OUTREACH_SYNC_OVERLAP_MS = 2 * 60 * 60_000\n\n/** How long after its last send an enrollment's mail is still watched. */\nexport const OUTREACH_SYNC_WATCH_MS = 45 * 24 * 60 * 60_000\n\n/** The most pages of one search a run reads. */\nconst SEARCH_PAGES = 5\n/** Handled message ids a mailbox keeps, and an enrollment keeps. */\nconst MAILBOX_HANDLED_MAX = 500\nconst ENROLLMENT_HANDLED_MAX = 100\n/** Addresses in one `from:` search. */\nconst FROM_CHUNK = 15\n\ntype Firestore = FirebaseFirestore.Firestore\n\nexport interface OutreachSyncReport {\n  [key: string]: number\n  mailboxes: number\n  threads: number\n  replies: number\n  optOuts: number\n  bounces: number\n  postponed: number\n  paused: number\n}\n\ninterface SyncContext {\n  deps: OutreachRuntimeDeps\n  firestore: Firestore\n  orgId: string\n  mailbox: OutreachMailbox\n  client: GmailClient\n  selfAddresses: string[]\n  unsubscribeAddress: string | null\n  sequences: Map<string, OutreachSequence | null>\n  delta: OutreachMailboxHealthDelta\n  report: OutreachSyncReport\n  nowMs: number\n}\n\n/** Runs the sync job once — see the module note. */\nexport async function runOutreachSyncJob(\n  deps: OutreachRuntimeDeps,\n  context: { nowMs: number; deadlineMs: number },\n): Promise<OutreachSyncReport> {\n  const firestore = deps.firestore()\n  const report: OutreachSyncReport = {\n    mailboxes: 0,\n    threads: 0,\n    replies: 0,\n    optOuts: 0,\n    bounces: 0,\n    postponed: 0,\n    paused: 0,\n  }\n  const all = await firestore.collectionGroup(OUTREACH_COLLECTIONS.mailboxes).get()\n  const byOrg = new Map<string, OutreachMailbox[]>()\n  for (const doc of all.docs) {\n    const orgId = doc.ref.parent.parent?.id\n    const mailbox = readStoredOutreachMailbox(doc.id, doc.data())\n    if (!orgId || !mailbox || (mailbox.status !== 'connected' && mailbox.status !== 'paused')) continue\n    byOrg.set(orgId, [...(byOrg.get(orgId) ?? []), mailbox])\n  }\n  for (const [orgId, mailboxes] of byOrg) {\n    if (deps.now() >= context.deadlineMs) break\n    const orgSnapshot = await firestore.collection('orgs').doc(orgId).get()\n    const org = (orgSnapshot.exists ? orgSnapshot.data() : null) as Record<string, unknown> | null\n    if (!org || (await deps.orgRefusal(orgId, org))) continue\n    for (const mailbox of mailboxes) {\n      if (deps.now() >= context.deadlineMs) break\n      try {\n        await syncMailbox(deps, firestore, { orgId, mailbox, report, nowMs: context.nowMs })\n        report.mailboxes += 1\n      } catch (error) {\n        // One mailbox's failure is its own; the next mailbox is read. A grant\n        // Google refused is the mailbox's to reconnect.\n        if (isReconnectRequired(error)) {\n          await markOutreachMailboxReconnectRequired(firestore, {\n            orgId,\n            mailboxId: mailbox.id,\n            errorCode: error instanceof GmailTransportError ? error.code : 'invalid_grant',\n            nowMs: context.nowMs,\n          })\n        }\n        console.error('[outreach] syncing a mailbox failed', error)\n      }\n    }\n  }\n  return report\n}\n\n/** Every stub a search finds, a few pages deep. */\nasync function search(\n  client: GmailClient,\n  q: string,\n): Promise<Array<{ id: string; threadId: string }>> {\n  const found: Array<{ id: string; threadId: string }> = []\n  let pageToken: string | null = null\n  for (let page = 0; page < SEARCH_PAGES; page += 1) {\n    const list = await client.listMessages({ q, maxResults: 100, pageToken, includeSpamTrash: true })\n    found.push(...list.messages.filter((message) => message.id))\n    pageToken = list.nextPageToken\n    if (!pageToken) break\n  }\n  return found\n}\n\nasync function syncMailbox(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  input: { orgId: string; mailbox: OutreachMailbox; report: OutreachSyncReport; nowMs: number },\n): Promise<void> {\n  const { orgId, mailbox, report, nowMs } = input\n  const opened = await deps.openMailbox(mailbox.id)\n  if (opened.ok === false) {\n    if (opened.reason !== 'not-configured') {\n      await markOutreachMailboxReconnectRequired(firestore, {\n        orgId,\n        mailboxId: mailbox.id,\n        errorCode: opened.reason,\n        nowMs,\n      })\n    }\n    return\n  }\n  const unsubscribe = outreachUnsubscribeMailbox(mailbox.email)\n  const context: SyncContext = {\n    deps,\n    firestore,\n    orgId,\n    mailbox,\n    client: opened.client,\n    selfAddresses: [\n      mailbox.email,\n      mailbox.sendAs,\n      ...(mailbox.sendAsOptions ?? []).map((option) => option.email),\n    ].filter(Boolean),\n    unsubscribeAddress: unsubscribe?.address ?? null,\n    sequences: new Map(),\n    delta: emptyOutreachHealthDelta(),\n    report,\n    nowMs,\n  }\n\n  // The enrollments this mailbox is writing to, by thread and by address.\n  const watched = await outreachOrgCollection(firestore, orgId, 'enrollments')\n    .where('mailboxId', '==', mailbox.id)\n    .where('lastSentAtMs', '>=', nowMs - OUTREACH_SYNC_WATCH_MS)\n    .get()\n  const byThread = new Map<string, OutreachEnrollment>()\n  const byAddress = new Map<string, OutreachEnrollment>()\n  for (const doc of watched.docs) {\n    const enrollment = readStoredOutreachEnrollment(doc.id, doc.data())\n    if (!enrollment) continue\n    for (const threadId of enrollment.gmailThreadIds) byThread.set(threadId, enrollment)\n    const known = byAddress.get(enrollment.email)\n    if (!known || (enrollment.lastSentAtMs ?? 0) > (known.lastSentAtMs ?? 0)) byAddress.set(enrollment.email, enrollment)\n  }\n\n  const sinceMs = Math.max(Number(mailbox.sync?.throughMs) || 0, nowMs - OUTREACH_SYNC_LOOKBACK_MS) - OUTREACH_SYNC_OVERLAP_MS\n  const after = `after:${Math.floor(sinceMs / 1000)}`\n  // Every message this run or an earlier one handled outside an enrollment's\n  // thread; one message is handled once however many searches find it.\n  const handled = new Set(mailbox.sync?.handledMessageIds ?? [])\n  const newlyHandled: string[] = []\n  const markHandled = (id: string) => {\n    if (handled.has(id)) return\n    handled.add(id)\n    newlyHandled.push(id)\n  }\n  const fresh = (stub: { id: string; threadId: string }) => !handled.has(stub.id) && !byThread.has(stub.threadId)\n\n  // 1. The enrollments' own threads that have new mail.\n  const inbound = await search(context.client, `${after} -from:me`)\n  for (const threadId of new Set(inbound.map((stub) => stub.threadId))) {\n    const enrollment = byThread.get(threadId)\n    if (!enrollment) continue\n    const thread = await context.client.getFullThread(threadId)\n    report.threads += 1\n    await applyMessages(context, enrollment, thread.messages.map(outreachThreadMessageFromGmail))\n  }\n\n  // 2. Delivery reports outside those threads: a receiving server's bounce.\n  for (const stub of await search(context.client, `${after} from:(mailer-daemon OR postmaster)`)) {\n    if (!fresh(stub)) continue\n    const message = outreachThreadMessageFromGmail(await context.client.getFullMessage(stub.id))\n    const delivery = readOutreachDeliveryReport(message)\n    if (delivery?.kind === 'hard') {\n      for (const address of delivery.failedAddresses) {\n        const enrollment = byAddress.get(address)\n        if (enrollment) await applyMessages(context, enrollment, [message])\n      }\n    }\n    markHandled(stub.id)\n  }\n\n  // 3. Messages to the unsubscribe address: whoever wrote asked to leave.\n  if (unsubscribe) {\n    for (const stub of await search(context.client, `${after} to:${unsubscribe.address}`)) {\n      if (handled.has(stub.id)) continue\n      const metadata = await context.client.getMessage(stub.id, { metadataHeaders: ['From'] })\n      const from = emailAddressOf(metadata.headers.find((header) => header.name.toLowerCase() === 'from')?.value ?? '')\n      const address = normalizeContactEmail(from)\n      if (address && !context.selfAddresses.includes(address)) {\n        const enrollment = byAddress.get(address) ?? null\n        await recordOutreachOptOut(deps, {\n          orgId,\n          email: address,\n          source: 'unsubscribe',\n          enrollment,\n          hostIds: enrollment ? [enrollment.hostId] : [],\n          detail: 'Wrote to the unsubscribe address.',\n          nowMs,\n        })\n        report.optOuts += 1\n      }\n      markHandled(stub.id)\n    }\n  }\n\n  // 4. The people this mailbox writes to, answering in a thread of their own.\n  const addresses = [...byAddress.keys()]\n  for (let start = 0; start < addresses.length; start += FROM_CHUNK) {\n    const chunk = addresses.slice(start, start + FROM_CHUNK)\n    for (const stub of await search(context.client, `${after} from:(${chunk.join(' OR ')})`)) {\n      if (!fresh(stub)) continue\n      const message = outreachThreadMessageFromGmail(await context.client.getFullMessage(stub.id))\n      const enrollment = byAddress.get(normalizeContactEmail(emailAddressOf(message.from)) ?? '')\n      if (enrollment) await applyMessages(context, enrollment, [message])\n      markHandled(stub.id)\n    }\n  }\n\n  const paused = await applyOutreachMailboxHealth(deps, { orgId, mailboxId: mailbox.id, delta: context.delta })\n  if (paused) report.paused += 1\n  await mailboxRef(firestore, orgId, mailbox.id).update({\n    sync: {\n      throughMs: nowMs,\n      handledMessageIds: [...(mailbox.sync?.handledMessageIds ?? []), ...newlyHandled].slice(-MAILBOX_HANDLED_MAX),\n    },\n  })\n}\n\n/** The sequence an enrollment runs through, read once per run. */\nasync function sequenceOf(context: SyncContext, sequenceId: string): Promise<OutreachSequence | null> {\n  if (!context.sequences.has(sequenceId)) {\n    const snapshot = await outreachOrgCollection(context.firestore, context.orgId, 'sequences').doc(sequenceId).get()\n    context.sequences.set(sequenceId, readStoredOutreachSequence(sequenceId, snapshot.exists ? snapshot.data() : undefined))\n  }\n  return context.sequences.get(sequenceId) ?? null\n}\n\n/** A message's `Message-ID` in header form, or `null` when it carries none. */\nconst messageIdOf = (message: OutreachThreadMessage) => outreachMessageIdHeader(outreachHeader(message, 'Message-ID'))\n\n/** A bounce's diagnostic with the recipient's address taken out of it. */\nexport function scrubbedOutreachDiagnostic(diagnostic: string | null, email: string): string | null {\n  if (!diagnostic) return null\n  const pattern = new RegExp(email.replace(/[.*+?^${}()|[\\]\\\\]/g, '\\\\$&'), 'gi')\n  return diagnostic.replace(pattern, 'the address')\n}\n\n/** Files a message the person wrote on their timeline. */\nasync function fileInbound(context: SyncContext, enrollment: OutreachEnrollment, message: OutreachThreadMessage) {\n  const messageId = messageIdOf(message)\n  if (!messageId) return\n  await fileOutreachEmail(context.deps, {\n    orgId: context.orgId,\n    hostId: enrollment.hostId,\n    contactId: enrollment.contactId,\n    direction: 'inbound',\n    subject: message.subject,\n    from: emailAddressOf(message.from) ?? message.from,\n    to: context.mailbox.sendAs || context.mailbox.email,\n    messageId,\n    inReplyTo: outreachMessageIdHeader(outreachHeader(message, 'In-Reply-To')),\n    body: crmInboundExcerpt(message.textBody ?? message.snippet ?? '', message.htmlBody ?? ''),\n    atMs: message.internalDateMs,\n    byUid: '',\n  })\n}\n\n/**\n * What the new messages of one enrollment mean, done: the effects first,\n * each idempotent, then the event and the handled ids in one transaction.\n */\nasync function applyMessages(\n  context: SyncContext,\n  enrollment: OutreachEnrollment,\n  messages: readonly OutreachThreadMessage[],\n): Promise<void> {\n  const { deps, firestore, report, nowMs } = context\n  const decision: OutreachThreadDecision = decideOutreachThread({\n    messages,\n    recipient: enrollment.email,\n    handledMessageIds: enrollment.syncedMessageIds ?? [],\n    selfAddresses: context.selfAddresses,\n    unsubscribeAddress: context.unsubscribeAddress,\n    threadSubject: enrollment.threadSubject,\n  })\n  const freshIds = decision.classifications.map((classification) => classification.messageId).filter(Boolean)\n  if (!freshIds.length) return\n  const decidedBy: OutreachMessageClassification | null = decision.decidedBy\n  const decidingMessage = decidedBy ? messages.find((message) => message.id === decidedBy.messageId) ?? null : null\n  const lastSentMessageId = enrollment.messageIds[enrollment.messageIds.length - 1] ?? null\n\n  for (const classification of decision.classifications) {\n    const aboutRecipient =\n      !classification.bounce?.recipients.length || classification.bounce.recipients.includes(enrollment.email)\n    if (classification.kind === 'hard_bounce' && aboutRecipient) {\n      context.delta.bounces.push({ atMs: classification.atMs || nowMs, messageId: lastSentMessageId })\n    }\n    if (classification.complaint) {\n      context.delta.complaintAtMs = Math.max(context.delta.complaintAtMs ?? 0, classification.atMs || nowMs)\n    }\n  }\n\n  let event: OutreachEnrollmentEvent | null = null\n  let postponedTo: number | null = null\n  switch (decision.outcome) {\n    case 'opted_out': {\n      if (decidingMessage) await fileInbound(context, enrollment, decidingMessage)\n      await recordOutreachOptOut(deps, {\n        orgId: context.orgId,\n        email: enrollment.email,\n        source: decidedBy?.evidence?.startsWith('To:') ? 'unsubscribe' : 'opt_out_reply',\n        enrollment,\n        hostIds: [enrollment.hostId],\n        detail: decidedBy?.evidence ?? null,\n        nowMs,\n      })\n      report.optOuts += 1\n      break\n    }\n    case 'replied': {\n      if (decidingMessage) {\n        await fileInbound(context, enrollment, decidingMessage)\n        try {\n          await fileOutreachTask(deps, {\n            orgId: context.orgId,\n            hostId: enrollment.hostId,\n            contactId: enrollment.contactId,\n            dedupeKey: `reply:${messageIdOf(decidingMessage) ?? decidingMessage.id}`,\n            title: `Reply from ${enrollment.contactName || enrollment.email}`,\n            notes: crmInboundExcerpt(decidingMessage.textBody ?? decidingMessage.snippet ?? '', decidingMessage.htmlBody ?? '').slice(0, 500),\n            kind: 'email',\n            dueAtMs: nowMs,\n            assigneeUid: context.mailbox.connectedByUid,\n          })\n        } catch (error) {\n          console.error('[outreach] the reply task could not be filed', error)\n        }\n      }\n      context.delta.replies += 1\n      event = { type: 'reply', atMs: decidedBy?.atMs || nowMs, detail: decidedBy?.evidence ?? null }\n      report.replies += 1\n      break\n    }\n    case 'bounced': {\n      const diagnostic = scrubbedOutreachDiagnostic(decidedBy?.bounce?.diagnostic ?? decidedBy?.bounce?.status ?? null, enrollment.email)\n      await deps.suppressBouncedEmail({ email: enrollment.email, hostId: enrollment.hostId })\n      await addOutreachDoNotContact(firestore, {\n        orgId: context.orgId,\n        email: enrollment.email,\n        reason: 'hard_bounce',\n        source: 'runtime',\n        nowMs,\n        enrollmentId: enrollment.id,\n        sequenceId: enrollment.sequenceId,\n        detail: diagnostic,\n      })\n      event = { type: 'bounce', atMs: decidedBy?.atMs || nowMs, detail: diagnostic }\n      report.bounces += 1\n      break\n    }\n    case 'postpone': {\n      const sequence = await sequenceOf(context, enrollment.sequenceId)\n      postponedTo = postponeOutreachForAutoReply({\n        nextDueAtMs: enrollment.nextDueAtMs,\n        receivedAtMs: decidedBy?.atMs || nowMs,\n        timeZone: context.mailbox.timezone,\n        window: effectiveOutreachWindow(sequence?.settings.window, context.mailbox.window),\n        random: deps.random,\n      })\n      break\n    }\n    default:\n      break\n  }\n\n  const outcome = await applyOutreachEvent(firestore, {\n    orgId: context.orgId,\n    enrollmentId: enrollment.id,\n    event,\n    extra: (current) => {\n      const extra: Record<string, unknown> = {\n        syncedMessageIds: [...(current.syncedMessageIds ?? []), ...freshIds].slice(-ENROLLMENT_HANDLED_MAX),\n      }\n      const waiting = current.status === 'active' || current.status === 'paused'\n      if (postponedTo !== null && waiting && current.nextDueAtMs !== null && postponedTo > current.nextDueAtMs) {\n        extra['nextDueAtMs'] = postponedTo\n      }\n      return extra\n    },\n    nowMs,\n  })\n  if (postponedTo !== null && outcome.enrollment?.nextDueAtMs === postponedTo) report.postponed += 1\n  // The run's own view of the enrollment moves with it, so a second message\n  // of it in this run is judged against what this one did.\n  if (outcome.enrollment) Object.assign(enrollment, 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+{"version":3,"sources":["../../../../../../../libs/plugins/outreach/src/lib/runtime/sync-job.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 { normalizeContactEmail } from '@aglyn/aglyn/app-utils/contacts'\nimport { crmInboundExcerpt, emailAddressOf } from '@aglyn/aglyn/app-utils/crm-inbound'\nimport { outreachMessageIdHeader } from '../engine/compose'\nimport { readOutreachDeliveryReport } from '../engine/delivery-status'\nimport type { OutreachEnrollmentEvent } from '../engine/enrollment-state'\nimport { effectiveOutreachWindow, postponeOutreachForAutoReply } from '../engine/schedule'\nimport {\n  decideOutreachThread,\n  type OutreachMessageClassification,\n  type OutreachThreadDecision,\n} from '../engine/thread-classification'\nimport { outreachHeader, outreachThreadMessageFromGmail, type OutreachThreadMessage } from '../engine/thread-message'\nimport { mailboxRef } from '../mailboxes/mailbox-credentials'\nimport { markOutreachMailboxReconnectRequired } from '../mailboxes/mailbox-transport'\nimport {\n  OUTREACH_COLLECTIONS,\n  type OutreachEnrollment,\n  type OutreachMailbox,\n  type OutreachSequence,\n} from '../model/outreach.types'\nimport { addOutreachDoNotContact } from '../storage/do-not-contact-store'\nimport {\n  outreachEnrollmentLink,\n  outreachOrgCollection,\n  readStoredOutreachEnrollment,\n  readStoredOutreachMailbox,\n  readStoredOutreachSequence,\n} from '../storage/outreach-records'\nimport type { GmailClient } from '../transport/gmail-client'\nimport { GmailTransportError, isReconnectRequired } from '../transport/gmail-errors'\nimport { applyOutreachEvent, recordOutreachOptOut } from './enrollment-events'\nimport {\n  applyOutreachMailboxHealth,\n  emptyOutreachHealthDelta,\n  type OutreachMailboxHealthDelta,\n} from './mailbox-health-store'\nimport type { OutreachRuntimeDeps } from './runtime-deps'\nimport { markOutreachLeadWorking } from './lead-records'\nimport { fileOutreachEmail, fileOutreachTask } from './timeline'\nimport { outreachUnsubscribeMailbox } from './unsubscribe-link'\n\n/*==========================================\n * THE SYNC JOB (AGL-2981): every fifteen minutes, on the console.\n *\n * For each connected or paused mailbox, what came back since the last run —\n * read with `format=full`, turned into the engine's message shape and\n * classified by `decideOutreachThread`:\n *\n * - a REPLY stops the enrollment, files the message on the contact's\n *   timeline (once per `Message-ID`, under the capture address's own id for\n *   it) and gives the rep the task \"Reply from <name>\";\n * - an OUT-OF-OFFICE postpones the next step a working week from the reply;\n * - an OPT-OUT — a reply asking to be left alone, or a message to the\n *   `+unsubscribe` address the `mailto:` names — puts the address on the\n *   organization's do-not-contact list and off the site's `sales` topic,\n *   and stops every open enrollment of it;\n * - a HARD BOUNCE stops the enrollment, files the address on the platform's\n *   suppression list and the do-not-contact list.\n *\n * Four reads find those, each narrowed by Gmail rather than read in full:\n * the threads of this mailbox's enrollments that have new mail; delivery\n * reports outside those threads (a receiving server's own bounce), by\n * searching for the mail systems that send them; messages to the\n * unsubscribe address; and messages from the people this mailbox is\n * writing to, in a thread of their own.\n *\n * Every write it makes is idempotent — the do-not-contact list keeps its\n * first entry, a topic opt-out keeps its first moment, a timeline entry is\n * filed once per message — and the messages it handled are marked AFTER\n * their effects, on the enrollment and on the mailbox, so a run that dies\n * part-way repeats harmless work rather than skipping some. The mailbox's\n * health takes the run's bounces and complaints in one write at the end,\n * which is where it pauses itself.\n *==========================================*/\n\nexport { OUTREACH_SYNC_JOB_ID } from '../constants/runtime-jobs'\n\n/** The furthest back a run reads: a mailbox's first run, or one that fell behind. */\nexport const OUTREACH_SYNC_LOOKBACK_MS = 7 * 24 * 60 * 60_000\n\n/** How far a run reads back past the previous one, for mail Gmail indexed late. */\nexport const OUTREACH_SYNC_OVERLAP_MS = 2 * 60 * 60_000\n\n/** How long after its last send an enrollment's mail is still watched. */\nexport const OUTREACH_SYNC_WATCH_MS = 45 * 24 * 60 * 60_000\n\n/** The most pages of one search a run reads. */\nconst SEARCH_PAGES = 5\n/** Handled message ids a mailbox keeps, and an enrollment keeps. */\nconst MAILBOX_HANDLED_MAX = 500\nconst ENROLLMENT_HANDLED_MAX = 100\n/** Addresses in one `from:` search. */\nconst FROM_CHUNK = 15\n\ntype Firestore = FirebaseFirestore.Firestore\n\nexport interface OutreachSyncReport {\n  [key: string]: number\n  mailboxes: number\n  threads: number\n  replies: number\n  optOuts: number\n  bounces: number\n  postponed: number\n  paused: number\n}\n\ninterface SyncContext {\n  deps: OutreachRuntimeDeps\n  firestore: Firestore\n  orgId: string\n  mailbox: OutreachMailbox\n  client: GmailClient\n  selfAddresses: string[]\n  unsubscribeAddress: string | null\n  sequences: Map<string, OutreachSequence | null>\n  delta: OutreachMailboxHealthDelta\n  report: OutreachSyncReport\n  nowMs: number\n}\n\n/** Runs the sync job once — see the module note. */\nexport async function runOutreachSyncJob(\n  deps: OutreachRuntimeDeps,\n  context: { nowMs: number; deadlineMs: number },\n): Promise<OutreachSyncReport> {\n  const firestore = deps.firestore()\n  const report: OutreachSyncReport = {\n    mailboxes: 0,\n    threads: 0,\n    replies: 0,\n    optOuts: 0,\n    bounces: 0,\n    postponed: 0,\n    paused: 0,\n  }\n  const all = await firestore.collectionGroup(OUTREACH_COLLECTIONS.mailboxes).get()\n  const byOrg = new Map<string, OutreachMailbox[]>()\n  for (const doc of all.docs) {\n    const orgId = doc.ref.parent.parent?.id\n    const mailbox = readStoredOutreachMailbox(doc.id, doc.data())\n    if (!orgId || !mailbox || (mailbox.status !== 'connected' && mailbox.status !== 'paused')) continue\n    byOrg.set(orgId, [...(byOrg.get(orgId) ?? []), mailbox])\n  }\n  for (const [orgId, mailboxes] of byOrg) {\n    if (deps.now() >= context.deadlineMs) break\n    const orgSnapshot = await firestore.collection('orgs').doc(orgId).get()\n    const org = (orgSnapshot.exists ? orgSnapshot.data() : null) as Record<string, unknown> | null\n    if (!org || (await deps.orgRefusal(orgId, org))) continue\n    for (const mailbox of mailboxes) {\n      if (deps.now() >= context.deadlineMs) break\n      try {\n        await syncMailbox(deps, firestore, { orgId, mailbox, report, nowMs: context.nowMs })\n        report.mailboxes += 1\n      } catch (error) {\n        // One mailbox's failure is its own; the next mailbox is read. A grant\n        // Google refused is the mailbox's to reconnect.\n        if (isReconnectRequired(error)) {\n          await markOutreachMailboxReconnectRequired(firestore, {\n            orgId,\n            mailboxId: mailbox.id,\n            errorCode: error instanceof GmailTransportError ? error.code : 'invalid_grant',\n            nowMs: context.nowMs,\n          })\n        }\n        console.error('[outreach] syncing a mailbox failed', error)\n      }\n    }\n  }\n  return report\n}\n\n/** Every stub a search finds, a few pages deep. */\nasync function search(\n  client: GmailClient,\n  q: string,\n): Promise<Array<{ id: string; threadId: string }>> {\n  const found: Array<{ id: string; threadId: string }> = []\n  let pageToken: string | null = null\n  for (let page = 0; page < SEARCH_PAGES; page += 1) {\n    const list = await client.listMessages({ q, maxResults: 100, pageToken, includeSpamTrash: true })\n    found.push(...list.messages.filter((message) => message.id))\n    pageToken = list.nextPageToken\n    if (!pageToken) break\n  }\n  return found\n}\n\nasync function syncMailbox(\n  deps: OutreachRuntimeDeps,\n  firestore: Firestore,\n  input: { orgId: string; mailbox: OutreachMailbox; report: OutreachSyncReport; nowMs: number },\n): Promise<void> {\n  const { orgId, mailbox, report, nowMs } = input\n  const opened = await deps.openMailbox(mailbox.id)\n  if (opened.ok === false) {\n    if (opened.reason !== 'not-configured') {\n      await markOutreachMailboxReconnectRequired(firestore, {\n        orgId,\n        mailboxId: mailbox.id,\n        errorCode: opened.reason,\n        nowMs,\n      })\n    }\n    return\n  }\n  const unsubscribe = outreachUnsubscribeMailbox(mailbox.email)\n  const context: SyncContext = {\n    deps,\n    firestore,\n    orgId,\n    mailbox,\n    client: opened.client,\n    selfAddresses: [\n      mailbox.email,\n      mailbox.sendAs,\n      ...(mailbox.sendAsOptions ?? []).map((option) => option.email),\n    ].filter(Boolean),\n    unsubscribeAddress: unsubscribe?.address ?? null,\n    sequences: new Map(),\n    delta: emptyOutreachHealthDelta(),\n    report,\n    nowMs,\n  }\n\n  // The enrollments this mailbox is writing to, by thread and by address.\n  const watched = await outreachOrgCollection(firestore, orgId, 'enrollments')\n    .where('mailboxId', '==', mailbox.id)\n    .where('lastSentAtMs', '>=', nowMs - OUTREACH_SYNC_WATCH_MS)\n    .get()\n  const byThread = new Map<string, OutreachEnrollment>()\n  const byAddress = new Map<string, OutreachEnrollment>()\n  for (const doc of watched.docs) {\n    const enrollment = readStoredOutreachEnrollment(doc.id, doc.data())\n    if (!enrollment) continue\n    for (const threadId of enrollment.gmailThreadIds) byThread.set(threadId, enrollment)\n    const known = byAddress.get(enrollment.email)\n    if (!known || (enrollment.lastSentAtMs ?? 0) > (known.lastSentAtMs ?? 0)) byAddress.set(enrollment.email, enrollment)\n  }\n\n  const sinceMs = Math.max(Number(mailbox.sync?.throughMs) || 0, nowMs - OUTREACH_SYNC_LOOKBACK_MS) - OUTREACH_SYNC_OVERLAP_MS\n  const after = `after:${Math.floor(sinceMs / 1000)}`\n  // Every message this run or an earlier one handled outside an enrollment's\n  // thread; one message is handled once however many searches find it.\n  const handled = new Set(mailbox.sync?.handledMessageIds ?? [])\n  const newlyHandled: string[] = []\n  const markHandled = (id: string) => {\n    if (handled.has(id)) return\n    handled.add(id)\n    newlyHandled.push(id)\n  }\n  const fresh = (stub: { id: string; threadId: string }) => !handled.has(stub.id) && !byThread.has(stub.threadId)\n\n  // 1. The enrollments' own threads that have new mail.\n  const inbound = await search(context.client, `${after} -from:me`)\n  for (const threadId of new Set(inbound.map((stub) => stub.threadId))) {\n    const enrollment = byThread.get(threadId)\n    if (!enrollment) continue\n    const thread = await context.client.getFullThread(threadId)\n    report.threads += 1\n    await applyMessages(context, enrollment, thread.messages.map(outreachThreadMessageFromGmail))\n  }\n\n  // 2. Delivery reports outside those threads: a receiving server's bounce.\n  for (const stub of await search(context.client, `${after} from:(mailer-daemon OR postmaster)`)) {\n    if (!fresh(stub)) continue\n    const message = outreachThreadMessageFromGmail(await context.client.getFullMessage(stub.id))\n    const delivery = readOutreachDeliveryReport(message)\n    if (delivery?.kind === 'hard') {\n      for (const address of delivery.failedAddresses) {\n        const enrollment = byAddress.get(address)\n        if (enrollment) await applyMessages(context, enrollment, [message])\n      }\n    }\n    markHandled(stub.id)\n  }\n\n  // 3. Messages to the unsubscribe address: whoever wrote asked to leave.\n  if (unsubscribe) {\n    for (const stub of await search(context.client, `${after} to:${unsubscribe.address}`)) {\n      if (handled.has(stub.id)) continue\n      const metadata = await context.client.getMessage(stub.id, { metadataHeaders: ['From'] })\n      const from = emailAddressOf(metadata.headers.find((header) => header.name.toLowerCase() === 'from')?.value ?? '')\n      const address = normalizeContactEmail(from)\n      if (address && !context.selfAddresses.includes(address)) {\n        const enrollment = byAddress.get(address) ?? null\n        await recordOutreachOptOut(deps, {\n          orgId,\n          email: address,\n          source: 'unsubscribe',\n          enrollment,\n          hostIds: enrollment ? [enrollment.hostId] : [],\n          detail: 'Wrote to the unsubscribe address.',\n          nowMs,\n        })\n        report.optOuts += 1\n      }\n      markHandled(stub.id)\n    }\n  }\n\n  // 4. The people this mailbox writes to, answering in a thread of their own.\n  const addresses = [...byAddress.keys()]\n  for (let start = 0; start < addresses.length; start += FROM_CHUNK) {\n    const chunk = addresses.slice(start, start + FROM_CHUNK)\n    for (const stub of await search(context.client, `${after} from:(${chunk.join(' OR ')})`)) {\n      if (!fresh(stub)) continue\n      const message = outreachThreadMessageFromGmail(await context.client.getFullMessage(stub.id))\n      const enrollment = byAddress.get(normalizeContactEmail(emailAddressOf(message.from)) ?? '')\n      if (enrollment) await applyMessages(context, enrollment, [message])\n      markHandled(stub.id)\n    }\n  }\n\n  const paused = await applyOutreachMailboxHealth(deps, { orgId, mailboxId: mailbox.id, delta: context.delta })\n  if (paused) report.paused += 1\n  await mailboxRef(firestore, orgId, mailbox.id).update({\n    sync: {\n      throughMs: nowMs,\n      handledMessageIds: [...(mailbox.sync?.handledMessageIds ?? []), ...newlyHandled].slice(-MAILBOX_HANDLED_MAX),\n    },\n  })\n}\n\n/** The sequence an enrollment runs through, read once per run. */\nasync function sequenceOf(context: SyncContext, sequenceId: string): Promise<OutreachSequence | null> {\n  if (!context.sequences.has(sequenceId)) {\n    const snapshot = await outreachOrgCollection(context.firestore, context.orgId, 'sequences').doc(sequenceId).get()\n    context.sequences.set(sequenceId, readStoredOutreachSequence(sequenceId, snapshot.exists ? snapshot.data() : undefined))\n  }\n  return context.sequences.get(sequenceId) ?? null\n}\n\n/** A message's `Message-ID` in header form, or `null` when it carries none. */\nconst messageIdOf = (message: OutreachThreadMessage) => outreachMessageIdHeader(outreachHeader(message, 'Message-ID'))\n\n/** A bounce's diagnostic with the recipient's address taken out of it. */\nexport function scrubbedOutreachDiagnostic(diagnostic: string | null, email: string): string | null {\n  if (!diagnostic) return null\n  const pattern = new RegExp(email.replace(/[.*+?^${}()|[\\]\\\\]/g, '\\\\$&'), 'gi')\n  return diagnostic.replace(pattern, 'the address')\n}\n\n/** Files a message the person wrote on their timeline. */\nasync function fileInbound(context: SyncContext, enrollment: OutreachEnrollment, message: OutreachThreadMessage) {\n  const messageId = messageIdOf(message)\n  if (!messageId) return\n  await fileOutreachEmail(context.deps, {\n    orgId: context.orgId,\n    hostId: enrollment.hostId,\n    link: outreachEnrollmentLink(enrollment),\n    direction: 'inbound',\n    subject: message.subject,\n    from: emailAddressOf(message.from) ?? message.from,\n    to: context.mailbox.sendAs || context.mailbox.email,\n    messageId,\n    inReplyTo: outreachMessageIdHeader(outreachHeader(message, 'In-Reply-To')),\n    body: crmInboundExcerpt(message.textBody ?? message.snippet ?? '', message.htmlBody ?? ''),\n    atMs: message.internalDateMs,\n    byUid: '',\n  })\n}\n\n/**\n * What the new messages of one enrollment mean, done: the effects first,\n * each idempotent, then the event and the handled ids in one transaction.\n */\nasync function applyMessages(\n  context: SyncContext,\n  enrollment: OutreachEnrollment,\n  messages: readonly OutreachThreadMessage[],\n): Promise<void> {\n  const { deps, firestore, report, nowMs } = context\n  const decision: OutreachThreadDecision = decideOutreachThread({\n    messages,\n    recipient: enrollment.email,\n    handledMessageIds: enrollment.syncedMessageIds ?? [],\n    selfAddresses: context.selfAddresses,\n    unsubscribeAddress: context.unsubscribeAddress,\n    threadSubject: enrollment.threadSubject,\n  })\n  const freshIds = decision.classifications.map((classification) => classification.messageId).filter(Boolean)\n  if (!freshIds.length) return\n  const decidedBy: OutreachMessageClassification | null = decision.decidedBy\n  const decidingMessage = decidedBy ? messages.find((message) => message.id === decidedBy.messageId) ?? null : null\n  const lastSentMessageId = enrollment.messageIds[enrollment.messageIds.length - 1] ?? null\n\n  for (const classification of decision.classifications) {\n    const aboutRecipient =\n      !classification.bounce?.recipients.length || classification.bounce.recipients.includes(enrollment.email)\n    if (classification.kind === 'hard_bounce' && aboutRecipient) {\n      context.delta.bounces.push({ atMs: classification.atMs || nowMs, messageId: lastSentMessageId })\n    }\n    if (classification.complaint) {\n      context.delta.complaintAtMs = Math.max(context.delta.complaintAtMs ?? 0, classification.atMs || nowMs)\n    }\n  }\n\n  let event: OutreachEnrollmentEvent | null = null\n  let postponedTo: number | null = null\n  switch (decision.outcome) {\n    case 'opted_out': {\n      if (decidingMessage) await fileInbound(context, enrollment, decidingMessage)\n      await recordOutreachOptOut(deps, {\n        orgId: context.orgId,\n        email: enrollment.email,\n        source: decidedBy?.evidence?.startsWith('To:') ? 'unsubscribe' : 'opt_out_reply',\n        enrollment,\n        hostIds: [enrollment.hostId],\n        detail: decidedBy?.evidence ?? null,\n        nowMs,\n      })\n      report.optOuts += 1\n      break\n    }\n    case 'replied': {\n      if (decidingMessage) {\n        await fileInbound(context, enrollment, decidingMessage)\n        try {\n          await fileOutreachTask(deps, {\n            orgId: context.orgId,\n            hostId: enrollment.hostId,\n            link: outreachEnrollmentLink(enrollment),\n            dedupeKey: `reply:${messageIdOf(decidingMessage) ?? decidingMessage.id}`,\n            title: `Reply from ${enrollment.contactName || enrollment.email}`,\n            notes: crmInboundExcerpt(decidingMessage.textBody ?? decidingMessage.snippet ?? '', decidingMessage.htmlBody ?? '').slice(0, 500),\n            kind: 'email',\n            dueAtMs: nowMs,\n            assigneeUid: context.mailbox.connectedByUid,\n          })\n        } catch (error) {\n          console.error('[outreach] the reply task could not be filed', error)\n        }\n      }\n      // A lead somebody wrote back to is being worked (AGL-3234).\n      if (enrollment.target === 'lead' && enrollment.leadId) {\n        await markOutreachLeadWorking(firestore, { hostId: enrollment.hostId, leadId: enrollment.leadId })\n      }\n      context.delta.replies += 1\n      event = { type: 'reply', atMs: decidedBy?.atMs || nowMs, detail: decidedBy?.evidence ?? null }\n      report.replies += 1\n      break\n    }\n    case 'bounced': {\n      const diagnostic = scrubbedOutreachDiagnostic(decidedBy?.bounce?.diagnostic ?? decidedBy?.bounce?.status ?? null, enrollment.email)\n      await deps.suppressBouncedEmail({ email: enrollment.email, hostId: enrollment.hostId })\n      await addOutreachDoNotContact(firestore, {\n        orgId: context.orgId,\n        email: enrollment.email,\n        reason: 'hard_bounce',\n        source: 'runtime',\n        nowMs,\n        enrollmentId: enrollment.id,\n        sequenceId: enrollment.sequenceId,\n        detail: diagnostic,\n      })\n      event = { type: 'bounce', atMs: decidedBy?.atMs || nowMs, detail: diagnostic }\n      report.bounces += 1\n      break\n    }\n    case 'postpone': {\n      const sequence = await sequenceOf(context, enrollment.sequenceId)\n      postponedTo = postponeOutreachForAutoReply({\n        nextDueAtMs: enrollment.nextDueAtMs,\n        receivedAtMs: decidedBy?.atMs || nowMs,\n        timeZone: context.mailbox.timezone,\n        window: effectiveOutreachWindow(sequence?.settings.window, context.mailbox.window),\n        random: deps.random,\n      })\n      break\n    }\n    default:\n      break\n  }\n\n  const outcome = await applyOutreachEvent(firestore, {\n    orgId: context.orgId,\n    enrollmentId: enrollment.id,\n    event,\n    extra: (current) => {\n      const extra: Record<string, unknown> = {\n        syncedMessageIds: [...(current.syncedMessageIds ?? 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package/src/lib/runtime/timeline.d.ts

@@ -14,7 +14,7 @@
  * See the License for the specific language governing permissions and
  * limitations under the License.
  */
-import type { PluginRecordTaskKind, PluginRecordWrite } from '@aglyn/aglyn/plugin-manager/plugin-record-timeline';
+import type { PluginRecordLink, PluginRecordTaskKind, PluginRecordWrite } from '@aglyn/aglyn/plugin-manager/plugin-record-timeline';
 import type { OutreachTaskKind } from '../model/outreach.types';
 import type { OutreachRuntimeDeps } from './runtime-deps';
 /**
@@ -33,11 +33,12 @@ import type { OutreachRuntimeDeps } from './runtime-deps';
  */
 /** The record system's word for a step's task kind. */
 export declare const OUTREACH_TASK_KIND_TO_RECORD: Record<OutreachTaskKind, PluginRecordTaskKind>;
-/** Files one email on a contact; never throws. */
+/** Files one email on a person's record — the contact, or the lead while they are one (AGL-3234); never throws. */
 export declare function fileOutreachEmail(deps: Pick<OutreachRuntimeDeps, 'timeline'>, input: {
     orgId: string;
     hostId: string;
-    contactId: string;
+    /** The record the entry lands on: `{ contactId }` or `{ leadId }`. */
+    link: PluginRecordLink;
     direction: 'outbound' | 'inbound';
     subject: string;
     from: string;
@@ -57,7 +58,8 @@ export declare function fileOutreachEmail(deps: Pick<OutreachRuntimeDeps, 'timel
 export declare function fileOutreachTask(deps: Pick<OutreachRuntimeDeps, 'timeline'>, input: {
     orgId: string;
     hostId: string;
-    contactId: string;
+    /** The record the task lands on: `{ contactId }` or `{ leadId }`. */
+    link: PluginRecordLink;
     dedupeKey: string;
     title: string;
     notes?: string | null;

package/src/lib/runtime/timeline.js

@@ -32,7 +32,7 @@
     linkedin: 'todo',
     todo: 'todo'
 };
-/** Files one email on a contact; never throws. */ export async function fileOutreachEmail(deps, input) {
+/** Files one email on a person's record — the contact, or the lead while they are one (AGL-3234); never throws. */ export async function fileOutreachEmail(deps, input) {
     const writer = deps.timeline();
     if (!writer) return null;
     try {
@@ -40,9 +40,7 @@
         const written = await writer.logActivity({
             orgId: input.orgId,
             hostId: input.hostId,
-            link: {
-                contactId: input.contactId
-            },
+            link: input.link,
             sourcePluginId: OUTREACH_PLUGIN_ID,
             kind: 'email',
             atMs: input.atMs,
@@ -76,9 +74,7 @@
     return writer.createTask({
         orgId: input.orgId,
         hostId: input.hostId,
-        link: {
-            contactId: input.contactId
-        },
+        link: input.link,
         sourcePluginId: OUTREACH_PLUGIN_ID,
         dedupeKey: input.dedupeKey,
         title: input.title,