feat: Chief of Staff email pipeline with Slack approval flow

[nickleeke]

Summary

• Full email processing pipeline: Gmail Pub/Sub → pre-filter → Claude AI (Sonnet) → Slack approval → action execution
• Slack Block Kit UI with approve/edit/reject buttons for Nick's mobile workflow
• Acuity scheduling integration with 6-calendar availability checking and day protection rules
• VIP detection, venture routing (Smart College/Praxis/Personal), voice/tone matching
• Cron jobs for retry, batch summary, signature refresh, and VIP cache refresh
• Database migration with 9 new tables and 6 enums
• Fix: NODE_OPTIONS heap size for Docker runtime and build scripts

New Files (54 files, ~7000 lines)

• apps/web/app/api/chief-of-staff/ — webhook, Slack interactions, cron routes
• apps/web/utils/chief-of-staff/ — engine, tools, pre-filter, calendar, Acuity, Slack, VIP, shipping
• apps/web/config/system-prompt.md — Claude system prompt content
• apps/web/prisma/migrations/20260322... — database migration
• go-live-checklist.html — interactive deployment checklist

Test plan

• 227 test files pass (2444 tests, 0 failures)
• Deploy via Dockerfile on Railway (standalone server)
• Walk through go-live checklist (Pub/Sub, Slack app, Acuity, env vars)
• Send test email and verify Slack notification appears
• Test approve/edit/reject button interactions

🤖 Generated with Claude Code

[vercel]

@nickleeke is attempting to deploy a commit to the Inbox Zero OSS Program Team on Vercel.

A member of the Team first needs to authorize it.

[CLAassistant]

All committers have signed the CLA.

[cubic-dev-ai]

30 issues found across 61 files

Prompt for AI agents (unresolved issues)

Check if these issues are valid — if so, understand the root cause of each and fix them. If appropriate, use sub-agents to investigate and fix each issue separately.


<file name="apps/web/utils/chief-of-staff/pre-filter.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/pre-filter.ts:46">
P2: extractDomain parses the raw From header with /@([^>]+)/, which can capture the wrong substring when the display name or comments contain '@' (valid RFC 5322 format). This can mis-parse senderDomain and break allowlist/blocklist routing. Consider extracting the address portion first and then taking the last '@' domain.</violation>

<violation number="2" location="apps/web/utils/chief-of-staff/pre-filter.ts:61">
P2: End-anchored shipping domain regexes are tested against the raw From header, so common formatted headers like "Name" <tracking@ups.com> end with ">" and won’t match /ups\.com$/i. This causes shipping senders to be missed unless the subject keywords happen to match.</violation>

<violation number="3" location="apps/web/utils/chief-of-staff/pre-filter.ts:79">
P2: Allow/block domain comparisons only lowercase configured values; they don’t trim whitespace or strip a leading '@', so common config formats like "@example.com" won’t match senderDomain and rules silently miss.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/system-prompt.test.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/system-prompt.test.ts:5">
P2: Mock target mismatch: implementation imports "node:fs", so mocking "fs" won't intercept reads and the test may hit real files.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/engine.test.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/engine.test.ts:107">
P2: Test claims to verify correct model/system prompt but only checks key existence, missing assertions for `model` and concrete `system` value.</violation>
</file>

<file name="apps/web/.env.example">

<violation number="1" location="apps/web/.env.example:243">
P2: Duplicate CRON_SECRET entry in .env.example can override the earlier value; the later blank value may disable/break cron auth when loaded.</violation>
</file>

<file name="skill-source/references/calendar-intelligence.md">

<violation number="1" location="skill-source/references/calendar-intelligence.md:127">
P2: The decision tree allows FYI/~ prefixes to override blocking, but the Special Rules section says RMS Work events are always hard blocks regardless of prefix. This contradiction could cause implementers to ignore RMS conflicts that should block scheduling.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/slack/blocks.test.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/slack/blocks.test.ts:199">
P2: The urgent-marker assertion is tautological because the subject already contains "URGENT", so the regex passes even if the builder stops adding an urgency marker. This weakens coverage for the urgency indicator.</violation>
</file>

<file name="apps/web/app/api/chief-of-staff/webhook/route.ts">

<violation number="1" location="apps/web/app/api/chief-of-staff/webhook/route.ts:9">
P2: Webhook token validation is unconditionally enforced, so empty/unset verification token mode cannot work and valid Pub/Sub pushes may be rejected.</violation>

<violation number="2" location="apps/web/app/api/chief-of-staff/webhook/route.ts:18">
P2: Malformed Pub/Sub payloads will throw during JSON parsing before the 200 response is returned, defeating the intended immediate acknowledgment and causing retry loops for bad payloads.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/acuity/client.test.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/acuity/client.test.ts:18">
P2: Fake timers are enabled without guaranteed cleanup; if the test fails before `vi.useRealTimers()`, fake timers leak into subsequent tests.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/signatures/fetcher.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/signatures/fetcher.ts:14">
P2: Empty-string signatures are treated as cache misses because the cache-hit check requires `signatureHtml` to be truthy, causing repeated Gmail fetches for accounts with no signature.</violation>
</file>

<file name="go-live-checklist.html">

<violation number="1" location="go-live-checklist.html:695">
P3: `loadState` parses localStorage JSON without error handling, so malformed persisted data can throw and abort checklist initialization (progress bar/section state never initializes).</violation>
</file>

<file name="apps/web/config/system-prompt.md">

<violation number="1" location="apps/web/config/system-prompt.md:213">
P1: Scheduling is allowed to proceed when calendar conflict checks fail, which can cause bookings/reschedules to execute using incomplete availability data.</violation>

<violation number="2" location="apps/web/config/system-prompt.md:214">
P2: Prompt instructs drafting English responses for non‑English emails, which conflicts with the policy to reply in the language of the latest thread message.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/jobs/retry-failed.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/jobs/retry-failed.ts:49">
P2: retryFailedEmails never retries processing; it only increments retryCount, so failed emails will reach dead_letter without any reprocessing attempt.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/vip/detector.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/vip/detector.ts:20">
P1: `checkVipStatus` uses raw email strings for unique lookups and dedupe without canonicalization, which can miss cache/group matches and misclassify VIP status.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/calendar/day-protection.test.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/calendar/day-protection.test.ts:11">
P2: Test dates are parsed in the local timezone, but isDayProtected evaluates in America/Chicago, so the expected weekday can shift in different environments.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/calendar/day-protection.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/calendar/day-protection.ts:13">
P2: Intl.DateTimeFormat().format throws on invalid Date; isDayProtected doesn’t guard, so malformed startTime/endTime strings can crash scheduling instead of returning a safe result.</violation>
</file>

<file name="skill-source/SKILL.md">

<violation number="1" location="skill-source/SKILL.md:197">
P2: Prompt instructions conflict on sending vs drafting scheduling confirmations, creating ambiguous and potentially unsafe assistant behavior.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/calendar/checker.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/calendar/checker.ts:81">
P1: Events with no summary are skipped, which can hide real time conflicts and incorrectly mark slots as available.</violation>
</file>

<file name="chief-of-staff-bot-architecture.md">

<violation number="1" location="chief-of-staff-bot-architecture.md:249">
P2: Gmail Pub/Sub setup URL points to `/webhook/gmail`, but the actual webhook handler is `/api/chief-of-staff/webhook`, so following this doc will send Pub/Sub to a non-existent endpoint.</violation>

<violation number="2" location="chief-of-staff-bot-architecture.md:256">
P2: Slack interactivity URL points to `/slack/events`, but the actual handler is `/api/chief-of-staff/slack/interactions`, so Slack interactions will fail if configured per the doc.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/acuity/client.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/acuity/client.ts:61">
P2: Network-level fetch failures are not retried or wrapped in AcuityApiError; any thrown error will exit the loop immediately, bypassing the retry/structured error handling logic.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/tools.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/tools.ts:56">
P2: startTime/endTime strings are parsed without validation; Invalid Date inputs will throw in downstream availability checks (toISOString/Intl.DateTimeFormat).</violation>

<violation number="2" location="apps/web/utils/chief-of-staff/tools.ts:221">
P1: Unsanitized header interpolation allows CRLF header injection when constructing raw Gmail MIME drafts.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/system-prompt.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/system-prompt.ts:16">
P1: System prompt loading relies on `process.cwd()` and an unguarded sync read, which can throw `ENOENT` in deploy/runtime contexts where CWD differs from `apps/web`.</violation>
</file>

<file name="apps/web/utils/chief-of-staff/slack/actions.ts">

<violation number="1" location="apps/web/utils/chief-of-staff/slack/actions.ts:51">
P2: Slack action handlers lack state/idempotency guards, so repeated or conflicting actions can send/delete drafts multiple times and overwrite terminal statuses.</violation>
</file>

<file name="apps/web/app/api/chief-of-staff/webhook/process.ts">

<violation number="1" location="apps/web/app/api/chief-of-staff/webhook/process.ts:213">
P2: lastSyncedHistoryId advances even when message processing fails, so failed Gmail history entries can be skipped permanently without retry.</violation>

<violation number="2" location="apps/web/app/api/chief-of-staff/webhook/process.ts:340">
P2: shippingEvent.calendarEventId is hardcoded to "created" instead of storing the provider’s actual event ID from the insert response, which prevents reliable updates/deletes or reconciliation.</violation>
</file>

_{Reply with feedback, questions, or to request a fix. Tag @cubic-dev-ai to re-run a review.}

[cubic-dev-ai]

P1: Scheduling is allowed to proceed when calendar conflict checks fail, which can cause bookings/reschedules to execute using incomplete availability data.

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At apps/web/config/system-prompt.md, line 213:

<comment>Scheduling is allowed to proceed when calendar conflict checks fail, which can cause bookings/reschedules to execute using incomplete availability data.</comment>

<file context>
@@ -0,0 +1,227 @@
+| Gmail search returns no results | Report "Inbox clear — nothing new since last check" |
+| Can't determine email category | Default to **Client/Parent** if from a person, **Notification** if automated |
+| Acuity is unreachable | Draft response saying "Let me check my availability and get back to you shortly" |
+| Calendar check fails | Note the gap and proceed with Acuity-only data, flagging the limitation |
+| Email is in a language other than English | Note the language and attempt categorization; draft response in English with a note to Nick |
+| Email thread (not just single message) | Read the full thread for context before categorizing/drafting |
</file context>

[cubic-dev-ai]

P1: checkVipStatus uses raw email strings for unique lookups and dedupe without canonicalization, which can miss cache/group matches and misclassify VIP status.

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At apps/web/utils/chief-of-staff/vip/detector.ts, line 20:

<comment>`checkVipStatus` uses raw email strings for unique lookups and dedupe without canonicalization, which can miss cache/group matches and misclassify VIP status.</comment>

<file context>
@@ -0,0 +1,82 @@
+  prisma: PrismaClient,
+): Promise<VipResult> {
+  // 1. Check cache
+  const cached = await prisma.vipCache.findUnique({ where: { clientEmail } });
+  if (cached && Date.now() - cached.lastChecked.getTime() < CACHE_TTL_MS) {
+    let groupName: string | null = null;
</file context>

[cubic-dev-ai]

P1: Events with no summary are skipped, which can hide real time conflicts and incorrectly mark slots as available.

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At apps/web/utils/chief-of-staff/calendar/checker.ts, line 81:

<comment>Events with no summary are skipped, which can hide real time conflicts and incorrectly mark slots as available.</comment>

<file context>
@@ -0,0 +1,117 @@
+    const events = result.value.data.items ?? [];
+
+    for (const event of events) {
+      if (!event.summary) continue;
+      const parsed = parseEventPrefix(event.summary);
+      const eventStart = event.start?.dateTime ?? event.start?.date ?? "";
</file context>

[cubic-dev-ai]

P1: Unsanitized header interpolation allows CRLF header injection when constructing raw Gmail MIME drafts.

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At apps/web/utils/chief-of-staff/tools.ts, line 221:

<comment>Unsanitized header interpolation allows CRLF header injection when constructing raw Gmail MIME drafts.</comment>

<file context>
@@ -0,0 +1,267 @@
+      // Build raw MIME message
+      const headers: string[] = [
+        `To: ${to}`,
+        `Subject: ${subject}`,
+        `From: ${emailAddress}`,
+        "MIME-Version: 1.0",
</file context>

[cubic-dev-ai]

P1: System prompt loading relies on process.cwd() and an unguarded sync read, which can throw ENOENT in deploy/runtime contexts where CWD differs from apps/web.

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At apps/web/utils/chief-of-staff/system-prompt.ts, line 16:

<comment>System prompt loading relies on `process.cwd()` and an unguarded sync read, which can throw `ENOENT` in deploy/runtime contexts where CWD differs from `apps/web`.</comment>

<file context>
@@ -0,0 +1,68 @@
+
+function getBasePrompt(): string {
+  if (basePromptCache) return basePromptCache;
+  const promptPath = path.join(process.cwd(), "config", "system-prompt.md");
+  basePromptCache = fs.readFileSync(promptPath, "utf-8");
+  return basePromptCache;
</file context>

[cubic-dev-ai]

P2: startTime/endTime strings are parsed without validation; Invalid Date inputs will throw in downstream availability checks (toISOString/Intl.DateTimeFormat).

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At apps/web/utils/chief-of-staff/tools.ts, line 56:

<comment>startTime/endTime strings are parsed without validation; Invalid Date inputs will throw in downstream availability checks (toISOString/Intl.DateTimeFormat).</comment>

<file context>
@@ -0,0 +1,267 @@
+    execute: async ({ startTime, endTime, isVip }) => {
+      return checkCalendarAvailability({
+        calendarClient: calendarAuth,
+        startTime: new Date(startTime),
+        endTime: new Date(endTime),
+        isVip,
</file context>

[cubic-dev-ai]

P2: Slack action handlers lack state/idempotency guards, so repeated or conflicting actions can send/delete drafts multiple times and overwrite terminal statuses.

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At apps/web/utils/chief-of-staff/slack/actions.ts, line 51:

<comment>Slack action handlers lack state/idempotency guards, so repeated or conflicting actions can send/delete drafts multiple times and overwrite terminal statuses.</comment>

<file context>
@@ -0,0 +1,338 @@
+  } = params;
+
+  // 1. Look up CosPendingDraft by slackMessageTs
+  const draft = await prisma.cosPendingDraft.findUnique({
+    where: { slackMessageTs },
+  });
</file context>

[cubic-dev-ai]

P2: lastSyncedHistoryId advances even when message processing fails, so failed Gmail history entries can be skipped permanently without retry.

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At apps/web/app/api/chief-of-staff/webhook/process.ts, line 213:

<comment>lastSyncedHistoryId advances even when message processing fails, so failed Gmail history entries can be skipped permanently without retry.</comment>

<file context>
@@ -0,0 +1,561 @@
+    }
+
+    // Update lastSyncedHistoryId
+    const lastEntry = historyEntries[historyEntries.length - 1];
+    if (lastEntry?.id) {
+      await prisma.$executeRaw`
</file context>

[cubic-dev-ai]

P2: shippingEvent.calendarEventId is hardcoded to "created" instead of storing the provider’s actual event ID from the insert response, which prevents reliable updates/deletes or reconciliation.

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At apps/web/app/api/chief-of-staff/webhook/process.ts, line 340:

<comment>shippingEvent.calendarEventId is hardcoded to "created" instead of storing the provider’s actual event ID from the insert response, which prevents reliable updates/deletes or reconciliation.</comment>

<file context>
@@ -0,0 +1,561 @@
+          data: {
+            messageId,
+            emailAccountId: emailAccount.id,
+            calendarEventId: "created",
+            itemDescription,
+          },
</file context>

[cubic-dev-ai]

P3: loadState parses localStorage JSON without error handling, so malformed persisted data can throw and abort checklist initialization (progress bar/section state never initializes).

Prompt for AI agents

Check if this issue is valid — if so, understand the root cause and fix it. At go-live-checklist.html, line 695:

<comment>`loadState` parses localStorage JSON without error handling, so malformed persisted data can throw and abort checklist initialization (progress bar/section state never initializes).</comment>

<file context>
@@ -0,0 +1,750 @@
+  function loadState() {
+    const saved = localStorage.getItem(STORAGE_KEY);
+    if (!saved) return;
+    const state = JSON.parse(saved);
+    const checkboxes = document.querySelectorAll('.task input[type="checkbox"]');
+    checkboxes.forEach((cb, i) => {
</file context>