Merge branch 'feature/grouped-emails' of https://github.com/assemblycom/tasks-app into staging

Author: arpandhakal

src/app/api/notification/notification.helpers.ts

@@ -247,6 +247,16 @@ export const getEmailDetails = (
   }
 }
 
+// Escalating cadence tag prefixed to the subject line as the due date approaches (OUT-3861).
+export const REMINDER_ESCALATION_TAG: Record<TaskReminderType, string> = {
+  [TaskReminderType.NO_DUE_DATE_3D]: '[Reminder]',
+  [TaskReminderType.NO_DUE_DATE_7D]: '[Reminder]',
+  [TaskReminderType.DUE_DATE_BEFORE_3D]: '[Due Soon]',
+  [TaskReminderType.DUE_DATE_TODAY]: '[Due Soon]',
+  [TaskReminderType.DUE_DATE_OVERDUE_3D]: '[Overdue]',
+  [TaskReminderType.DUE_DATE_OVERDUE_7D]: '[Overdue]',
+}
+
 // Subjects intentionally omit any `<brandName> portal:` prefix — Copilot's email
 // service prepends that itself, and adding it here results in a duplicated prefix.
 export const getReminderEmailDetails = (

src/config/index.ts

@@ -49,3 +49,12 @@ export const showQueries = (() => {
 })()
 
 export const assemblyApiDomain = z.string().url().parse(process.env.NEXT_PUBLIC_ASSEMBLY_API_DOMAIN)
+
+// Workspaces whose single reminder emails use the task title as the subject, prefixed with the
+// escalating cadence tag (OUT-3861). Comma-separated workspace ids, e.g. C1: us-west-2_lg5zB-Utp.
+export const reminderSubjectOverrideWorkspaces = new Set(
+  (process.env.REMINDER_SUBJECT_OVERRIDE_WORKSPACES || '')
+    .split(',')
+    .map((id) => id.trim())
+    .filter(Boolean),
+)

src/jobs/notifications/flush-grouped-email.integration.test.ts

@@ -81,9 +81,9 @@ const seedEvent = async ({
   })
 }
 
-const unsentCount = async (windowKey: string): Promise<number> => {
+const totalCount = async (windowKey: string): Promise<number> => {
   const rows = await getTestDb().$queryRaw<{ count: bigint }[]>`
-    SELECT count(*) FROM "GroupedEmailEvents" WHERE "windowKey" = ${windowKey} AND "sentAt" IS NULL`
+    SELECT count(*) FROM "GroupedEmailEvents" WHERE "windowKey" = ${windowKey}`
   return Number(rows[0].count)
 }
 
@@ -99,7 +99,7 @@ beforeEach(async () => {
 afterAll(disconnectTestDb)
 
 describe('flush-grouped-email idempotency (real DB)', () => {
-  it('sends one grouped email for multiple events and marks every row as sent', async () => {
+  it('sends one grouped email for multiple events and deletes all rows on success', async () => {
     const window = 'win_multi_event'
     const taskA = await seedTask({ workspaceId: WS, assigneeId: CLIENT_A, assigneeType: 'client', companyId: COMPANY })
     const taskB = await seedTask({ workspaceId: WS, assigneeId: CLIENT_A, assigneeType: 'client', companyId: COMPANY })
@@ -120,7 +120,7 @@ describe('flush-grouped-email idempotency (real DB)', () => {
 
     expect(mockCreateNotification).toHaveBeenCalledTimes(1)
     expect(result).toMatchObject({ recipients: 1, sent: 1, sentGrouped: 1, sentIndividual: 0 })
-    expect(await unsentCount(window)).toBe(0)
+    expect(await totalCount(window)).toBe(0)
   })
 
   it('is idempotent: re-flushing a fully-sent window is a no-op', async () => {
@@ -142,8 +142,9 @@ describe('flush-grouped-email idempotency (real DB)', () => {
 
     await flushGroupedEmailRun({ workspaceId: WS, windowKey: window })
     expect(mockCreateNotification).toHaveBeenCalledTimes(1)
+    expect(await totalCount(window)).toBe(0)
 
-    // Second flush: all rows already have sentAt set — no email, skipped return.
+    // Second flush: rows were deleted — no email, skipped return.
     const result = await flushGroupedEmailRun({ workspaceId: WS, windowKey: window })
     expect(mockCreateNotification).toHaveBeenCalledTimes(1)
     expect(result).toMatchObject({ skipped: true })
@@ -169,14 +170,14 @@ describe('flush-grouped-email idempotency (real DB)', () => {
     mockCreateNotification.mockRejectedValueOnce(new Error('copilot 5xx'))
     await expect(flushGroupedEmailRun({ workspaceId: WS, windowKey: window })).rejects.toThrow('copilot 5xx')
 
-    // Rows are still unsent — retry can re-attempt.
-    expect(await unsentCount(window)).toBe(2)
+    // Failed run: rows are preserved so the retry can re-attempt.
+    expect(await totalCount(window)).toBe(2)
 
-    // Retry succeeds.
+    // Retry succeeds: rows are deleted.
     mockCreateNotification.mockResolvedValueOnce({ id: 'notif_2' })
     await flushGroupedEmailRun({ workspaceId: WS, windowKey: window })
     expect(mockCreateNotification).toHaveBeenCalledTimes(2)
-    expect(await unsentCount(window)).toBe(0)
+    expect(await totalCount(window)).toBe(0)
   })
 
   it('sends one email per recipient when the window holds events for multiple clients', async () => {
@@ -217,10 +218,10 @@ describe('flush-grouped-email idempotency (real DB)', () => {
     const recipients = mockCreateNotification.mock.calls.map((c) => c[0].recipientClientId).sort()
     expect(recipients).toEqual([CLIENT_A, CLIENT_B].sort())
     expect(result).toMatchObject({ recipients: 2, sent: 2, sentGrouped: 2, sentIndividual: 0 })
-    expect(await unsentCount(window)).toBe(0)
+    expect(await totalCount(window)).toBe(0)
   })
 
-  it('skips events for archived tasks and marks their rows sent without emailing', async () => {
+  it('skips events for archived tasks and deletes all rows on success', async () => {
     const window = 'win_archived'
     const archivedTask = await seedTask({
       workspaceId: WS,
@@ -244,11 +245,10 @@ describe('flush-grouped-email idempotency (real DB)', () => {
     // Only the live task appears in the grouped email (1 event); individual snapshot path.
     expect(mockCreateNotification).toHaveBeenCalledTimes(1)
     expect(result).toMatchObject({ sentGrouped: 0, sentIndividual: 1 })
-    // All rows are marked sent regardless of whether the task was live.
-    expect(await unsentCount(window)).toBe(0)
+    expect(await totalCount(window)).toBe(0)
   })
 
-  it('marks the recipient sent without emailing when every task in the window was archived', async () => {
+  it('deletes rows without emailing when every task in the window was archived', async () => {
     const window = 'win_all_archived'
     const archivedTask = await seedTask({
       workspaceId: WS,
@@ -263,10 +263,10 @@ describe('flush-grouped-email idempotency (real DB)', () => {
 
     expect(mockCreateNotification).not.toHaveBeenCalled()
     expect(result).toMatchObject({ sent: 0 })
-    expect(await unsentCount(window)).toBe(0)
+    expect(await totalCount(window)).toBe(0)
   })
 
-  it('marks the recipient sent without emailing when every task in the window was soft-deleted', async () => {
+  it('deletes rows without emailing when every task in the window was soft-deleted', async () => {
     const window = 'win_all_deleted'
     const deletedTask = await seedTask({
       workspaceId: WS,
@@ -281,6 +281,6 @@ describe('flush-grouped-email idempotency (real DB)', () => {
 
     expect(mockCreateNotification).not.toHaveBeenCalled()
     expect(result).toMatchObject({ sent: 0 })
-    expect(await unsentCount(window)).toBe(0)
+    expect(await totalCount(window)).toBe(0)
   })
 })

src/jobs/notifications/flush-grouped-email.test.ts

@@ -103,7 +103,7 @@ describe('flushGroupedEmailRun', () => {
     expect(args).toMatchObject({ senderId: 'iu_1', recipientClientId: 'client_1', recipientCompanyId: 'company_1' })
     expect(args.content.totalEventCount).toBe(2)
     expect(mockCreateNotification).not.toHaveBeenCalled()
-    expect(mockExecuteRaw).toHaveBeenCalledTimes(1) // markRecipientSent
+    expect(mockExecuteRaw).toHaveBeenCalledTimes(2) // markRecipientSent + deleteWindowRows
     expect(result).toMatchObject({ recipients: 1, sent: 1, sentGrouped: 1, sentIndividual: 0 })
   })
 
@@ -116,7 +116,7 @@ describe('flushGroupedEmailRun', () => {
     expect(mockCreateNotification).toHaveBeenCalledWith(expect.objectContaining({ recipientClientId: 'client_1' }))
     expect(mockSendGroupedEmail).not.toHaveBeenCalled()
     expect(mockGetInternalUsers).not.toHaveBeenCalled() // no workspace IU needed for the individual path
-    expect(mockExecuteRaw).toHaveBeenCalledTimes(1)
+    expect(mockExecuteRaw).toHaveBeenCalledTimes(2) // markRecipientSent + deleteWindowRows
     expect(result).toMatchObject({ recipients: 1, sent: 1, sentGrouped: 0, sentIndividual: 1 })
   })
 
@@ -166,7 +166,7 @@ describe('flushGroupedEmailRun', () => {
 
     expect(mockSendGroupedEmail).not.toHaveBeenCalled()
     expect(mockCreateNotification).not.toHaveBeenCalled()
-    expect(mockExecuteRaw).toHaveBeenCalledTimes(1)
+    expect(mockExecuteRaw).toHaveBeenCalledTimes(2) // markRecipientSent + deleteWindowRows
     expect(result).toMatchObject({ sent: 0, sentGrouped: 0, sentIndividual: 0 })
   })
 
@@ -177,7 +177,7 @@ describe('flushGroupedEmailRun', () => {
 
     expect(mockCreateNotification).toHaveBeenCalledTimes(2)
     expect(mockSendGroupedEmail).not.toHaveBeenCalled()
-    expect(mockExecuteRaw).toHaveBeenCalledTimes(2)
+    expect(mockExecuteRaw).toHaveBeenCalledTimes(3) // markRecipientSent x2 + deleteWindowRows
     expect(result).toMatchObject({ recipients: 2, sent: 2, sentGrouped: 0, sentIndividual: 2 })
   })
 
@@ -191,7 +191,7 @@ describe('flushGroupedEmailRun', () => {
 
     expect(mockCreateNotification).toHaveBeenCalledTimes(2)
     expect(mockCreateNotification.mock.calls[1][0]).toMatchObject({ senderCompanyId: undefined })
-    expect(mockExecuteRaw).toHaveBeenCalledTimes(1)
+    expect(mockExecuteRaw).toHaveBeenCalledTimes(2) // markRecipientSent + deleteWindowRows
   })
 
   it('does not mark a recipient sent when their send fails (so a retry re-sends)', async () => {

src/jobs/notifications/flush-grouped-email.ts

@@ -40,6 +40,9 @@ const readUnsentWindowEvents = (db: ReturnType<typeof DBClient.getInstance>, win
     FROM "GroupedEmailEvents"
     WHERE "windowKey" = ${windowKey} AND "sentAt" IS NULL`
 
+const deleteWindowRows = (db: ReturnType<typeof DBClient.getInstance>, windowKey: string) =>
+  db.$executeRaw`DELETE FROM "GroupedEmailEvents" WHERE "windowKey" = ${windowKey} AND "sentAt" IS NOT NULL`
+
 const markRecipientSent = (
   db: ReturnType<typeof DBClient.getInstance>,
   windowKey: string,
@@ -169,6 +172,16 @@ export const flushGroupedEmailRun = async (payload: FlushGroupedEmailPayload) =>
     })
   }
 
+  try {
+    await deleteWindowRows(db, windowKey)
+  } catch (err) {
+    logger.error('flush-grouped-email: window cleanup failed, rows left with sentAt set', {
+      workspaceId,
+      windowKey,
+      error: serializeError(err),
+    })
+  }
+
   logger.log('flush-grouped-email: run summary', {
     workspaceId,
     windowKey,

src/jobs/notifications/send-reminder-email.test.ts

@@ -3,6 +3,8 @@ import { CopilotAPI } from '@/utils/CopilotAPI'
 import { TaskReminderType } from '@prisma/client'
 import { sendReminderEmail } from './send-reminder-email'
 
+jest.mock('@/config', () => ({ reminderSubjectOverrideWorkspaces: new Set(['ws_override']) }))
+
 const workspace: WorkspaceResponse = {
   id: 'ws_1',
   brandName: 'Acme',
@@ -115,4 +117,41 @@ describe('sendReminderEmail', () => {
       }),
     ).rejects.toThrow('copilot 5xx')
   })
+
+  it('uses the task title with the escalating tag as subject for override workspaces', async () => {
+    const createNotification = jest.fn().mockResolvedValue({ id: 'notif_4', createdAt: '2026-05-25T00:00:00Z' })
+
+    await sendReminderEmail({
+      task,
+      recipientClientId: 'client_1',
+      recipientCompanyId: 'company_1',
+      reminderType: TaskReminderType.DUE_DATE_OVERDUE_3D,
+      isCompanyRecipient: false,
+      workspace: { ...workspace, id: 'ws_override' },
+      copilot: buildCopilotMock(createNotification),
+    })
+
+    const payload = createNotification.mock.calls[0][0]
+    expect(payload.deliveryTargets.email.subject).toBe('[Overdue] Submit timesheet')
+    // Only the subject is customized — the rest of the reminder copy is unchanged.
+    expect(payload.deliveryTargets.email.header).toBe('A task was assigned to you')
+    expect(payload.deliveryTargets.email.title).toBe('View task')
+  })
+
+  it('keeps the generic subject for workspaces not in the override set', async () => {
+    const createNotification = jest.fn().mockResolvedValue({ id: 'notif_5', createdAt: '2026-05-25T00:00:00Z' })
+
+    await sendReminderEmail({
+      task,
+      recipientClientId: 'client_1',
+      recipientCompanyId: 'company_1',
+      reminderType: TaskReminderType.DUE_DATE_OVERDUE_3D,
+      isCompanyRecipient: false,
+      workspace,
+      copilot: buildCopilotMock(createNotification),
+    })
+
+    const payload = createNotification.mock.calls[0][0]
+    expect(payload.deliveryTargets.email.subject).toBe('[Overdue] Task was due 3 days ago')
+  })
 })

src/jobs/notifications/send-reminder-email.ts

@@ -1,6 +1,7 @@
 import 'server-only'
 
-import { getReminderEmailDetails } from '@/app/api/notification/notification.helpers'
+import { getReminderEmailDetails, REMINDER_ESCALATION_TAG } from '@/app/api/notification/notification.helpers'
+import { reminderSubjectOverrideWorkspaces } from '@/config'
 import { NotificationRequestBody, WorkspaceResponse } from '@/types/common'
 import { CopilotAPI } from '@/utils/CopilotAPI'
 import { Task, TaskReminderType } from '@prisma/client'
@@ -28,14 +29,20 @@ export const sendReminderEmail = async ({
 }: SendReminderEmailArgs): Promise<string> => {
   const details = getReminderEmailDetails(workspace, task, isCompanyRecipient)[reminderType]
 
+  // For opted-in workspaces, mirror the customized assignment email by using the task title as the
+  // subject, prefixed with the escalating cadence tag (OUT-3861).
+  const subject = reminderSubjectOverrideWorkspaces.has(workspace.id)
+    ? `${REMINDER_ESCALATION_TAG[reminderType]} ${task.title}`
+    : details.subject
+
   const payload: NotificationRequestBody = {
     senderId: task.createdById,
     senderType: 'internalUser',
     recipientClientId,
     recipientCompanyId: recipientCompanyId ?? undefined,
     deliveryTargets: {
       email: {
-        subject: details.subject,
+        subject,
         header: details.header,
         title: details.title,
         body: details.body,