test(03-10): add RED tests for CR-03 fail-closed creds + WR-01 backoff index

- Add mockDecryptPassword to vi.hoisted() so tests can control loadClientForUser behavior
- Add vi.mock for broker/crypto.js to enable CR-03 scenario
- Introduce wireMockChain() helper that differentiates credential vs outbox db selects
- CR-03 RED: credential-load failure must leave row pending, not call createFastmailClient('')
- WR-01 RED: first transient retry must use BACKOFF_SECONDS[0]=15s not BACKOFF_SECONDS[1]=60s
- Update FAKE_CRED_ROW so loadClientForUser can return a real credential-shaped row

apps/api/tests/broker/outboxWorker.test.ts

@@ -34,6 +34,7 @@ const {
   mockWherePending,
   mockFromFn,
   mockSelectFn,
+  mockDecryptPassword,
 } = vi.hoisted(() => {
   const mockUpdateSet = vi.fn().mockReturnValue({ where: vi.fn().mockResolvedValue(undefined) })
   const mockUpdate = vi.fn().mockReturnValue({ set: mockUpdateSet })
@@ -42,11 +43,20 @@ const {
   const mockWherePending = vi.fn().mockImplementation(() => Promise.resolve([] as unknown[]))
   const mockFromFn = vi.fn().mockReturnValue({ where: mockWherePending })
   const mockSelectFn = vi.fn().mockReturnValue({ from: mockFromFn })
-  return { mockUpdateSet, mockUpdate, mockWherePending, mockFromFn, mockSelectFn }
+  // By default returns a dummy password so loadClientForUser succeeds
+  const mockDecryptPassword = vi.fn().mockReturnValue('app-password')
+  return { mockUpdateSet, mockUpdate, mockWherePending, mockFromFn, mockSelectFn, mockDecryptPassword }
 })
 
 let mockPendingRows: unknown[] = []
 
+// Fake credential row returned by loadClientForUser's db.select().from(memberCredentials).where()
+const FAKE_CRED_ROW = {
+  userId: 42,
+  fastmailEmail: 'test@fastmail.com',
+  encryptedPassword: '{"iv":"aa","authTag":"bb","ciphertext":"cc"}',
+}
+
 vi.mock('../../src/db/client.js', () => ({
   db: {
     select: mockSelectFn,
@@ -73,6 +83,11 @@ vi.mock('../../src/broker/client.js', () => ({
   }),
 }))
 
+// Mock crypto — controls whether loadClientForUser succeeds or throws (CR-03 tests)
+vi.mock('../../src/broker/crypto.js', () => ({
+  decryptPassword: mockDecryptPassword,
+}))
+
 // Default payload is form JSON (the worker must build ICS from this — not pass raw JSON to CalDAV)
 const DEFAULT_FORM_PAYLOAD = JSON.stringify({
   title: 'Lunch',
@@ -104,17 +119,40 @@ const makeRow = (overrides: Record<string, unknown> = {}) => ({
 const makeResponse = (status: number): Response =>
   ({ status, ok: status >= 200 && status < 300, headers: new Headers() }) as unknown as Response
 
+// Helper: wire db mock so outbox queries return mockPendingRows and credential queries return FAKE_CRED_ROW
+// This is called in each beforeEach after vi.clearAllMocks() to restore the mock chain.
+function wireMockChain() {
+  mockUpdateSet.mockReturnValue({ where: vi.fn().mockResolvedValue(undefined) })
+  mockUpdate.mockReturnValue({ set: mockUpdateSet })
+  // mockFromFn differentiates by table argument:
+  // - memberCredentials table → returns FAKE_CRED_ROW (so loadClientForUser succeeds by default)
+  // - anything else → returns mockPendingRows (outbox query)
+  mockFromFn.mockImplementation((table: unknown) => {
+    // Drizzle table objects have a Symbol.for('drizzle:Name') property and a [Table.Symbol.Name].
+    // The safest approach: JSON.stringify often includes the table config name.
+    let isCred = false
+    try {
+      isCred = JSON.stringify(table).includes('member_credentials')
+    } catch {
+      // table not serializable — not a credential table
+    }
+    return {
+      where: isCred
+        ? vi.fn().mockResolvedValue([FAKE_CRED_ROW])
+        : mockWherePending,
+    }
+  })
+  mockWherePending.mockImplementation(() => Promise.resolve(mockPendingRows))
+  mockSelectFn.mockReturnValue({ from: mockFromFn })
+  // Default: decryptPassword succeeds
+  mockDecryptPassword.mockReturnValue('app-password')
+}
+
 describe('runOutboxDrain — state transitions', () => {
   beforeEach(() => {
     vi.clearAllMocks()
     mockPendingRows = []
-    // Restore mock chain after clearAllMocks:
+    wireMockChain()
-    //   db.select().from(table).where(and(cond1, cond2)) → Promise<rows>
-    mockUpdateSet.mockReturnValue({ where: vi.fn().mockResolvedValue(undefined) })
-    mockUpdate.mockReturnValue({ set: mockUpdateSet })
-    mockWherePending.mockImplementation(() => Promise.resolve(mockPendingRows))
-    mockFromFn.mockReturnValue({ where: mockWherePending })
-    mockSelectFn.mockReturnValue({ from: mockFromFn })
   })
 
   it('transitions pending→done on 204 response and triggers re-sync (D-06)', async () => {
@@ -188,11 +226,7 @@ describe('runOutboxDrain — ICS building from form JSON (CR-02)', () => {
   beforeEach(() => {
     vi.clearAllMocks()
     mockPendingRows = []
-    mockUpdateSet.mockReturnValue({ where: vi.fn().mockResolvedValue(undefined) })
+    wireMockChain()
-    mockUpdate.mockReturnValue({ set: mockUpdateSet })
-    mockWherePending.mockImplementation(() => Promise.resolve(mockPendingRows))
-    mockFromFn.mockReturnValue({ where: mockWherePending })
-    mockSelectFn.mockReturnValue({ from: mockFromFn })
   })
 
   it('create row: icsString passed to createCalendarEvent starts with BEGIN:VCALENDAR and contains SUMMARY', async () => {
@@ -243,11 +277,7 @@ describe('runOutboxDrain — edit-as-move ordering (D-04)', () => {
   beforeEach(() => {
     vi.clearAllMocks()
     mockPendingRows = []
-    mockUpdateSet.mockReturnValue({ where: vi.fn().mockResolvedValue(undefined) })
+    wireMockChain()
-    mockUpdate.mockReturnValue({ set: mockUpdateSet })
-    mockWherePending.mockImplementation(() => Promise.resolve(mockPendingRows))
-    mockFromFn.mockReturnValue({ where: mockWherePending })
-    mockSelectFn.mockReturnValue({ from: mockFromFn })
   })
 
   it('processes the create row BEFORE the delete row when both share a groupId', async () => {
@@ -288,3 +318,56 @@ describe('runOutboxDrain — edit-as-move ordering (D-04)', () => {
     expect(createCall).toBeLessThan(deleteCall)
   })
 })
+
+describe('runOutboxDrain — fail closed on bad credentials (CR-03) + backoff index fix (WR-01)', () => {
+  beforeEach(() => {
+    vi.clearAllMocks()
+    mockPendingRows = []
+    wireMockChain()
+  })
+
+  it('CR-03: credential-load failure leaves row pending and never calls createFastmailClient with empty credentials', async () => {
+    // Make decryptPassword throw so loadClientForUser throws
+    mockDecryptPassword.mockImplementation(() => { throw new Error('bad credentials') })
+
+    const { createFastmailClient } = await import('../../src/broker/client.js')
+    mockPendingRows = [makeRow()]
+
+    await runOutboxDrain()
+
+    // The row must NOT be updated to done/failed/dead — it stays pending (outer catch handles it)
+    const updateCalls = mockUpdateSet.mock.calls
+    const anyStatusChange = updateCalls.some((call) => {
+      const arg = call[0] as { status?: string }
+      return arg?.status !== undefined
+    })
+    expect(anyStatusChange).toBe(false)
+
+    // createFastmailClient must NEVER be called with empty-string credentials
+    const emptyCalls = vi.mocked(createFastmailClient).mock.calls.filter(
+      ([email, password]) => email === '' || password === ''
+    )
+    expect(emptyCalls.length).toBe(0)
+  })
+
+  it('WR-01: first transient failure (attemptCount=0) sets backoff to ~15s (BACKOFF_SECONDS[0])', async () => {
+    const { createCalendarEvent } = await import('../../src/broker/write.js')
+    vi.mocked(createCalendarEvent).mockResolvedValue(makeResponse(500))
+    const row = makeRow({ attemptCount: 0 })
+    mockPendingRows = [row]
+
+    const beforeDrain = Date.now()
+    await runOutboxDrain()
+    const afterDrain = Date.now()
+
+    const setArg = mockUpdateSet.mock.calls[0]?.[0] as { nextAttemptAt?: Date; attemptCount?: number }
+    expect(setArg?.attemptCount).toBe(1)
+
+    // WR-01: nextAttemptAt must be ~15s in the future (BACKOFF_SECONDS[0] = 15)
+    // Allow ±2s for execution overhead
+    const expectedMinMs = beforeDrain + 14_000
+    const expectedMaxMs = afterDrain + 16_000
+    expect(setArg?.nextAttemptAt?.getTime()).toBeGreaterThanOrEqual(expectedMinMs)
+    expect(setArg?.nextAttemptAt?.getTime()).toBeLessThanOrEqual(expectedMaxMs)
+  })
+})