OUT-3730 | Trigger.dev job: send-task-reminders scheduled task

src/app/api/notification/__snapshots__/notification.helpers.test.ts.snap

@@ -10,7 +10,7 @@ Please make sure to complete this task by the due date.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to your company",
-    "subject": "Acme portal: [Due Soon] Task due in 3 days",
+    "subject": "[Due Soon] Task due in 3 days",
     "title": "View task",
   },
   "DUE_DATE_OVERDUE_3D": {
@@ -19,7 +19,7 @@ Please make sure to complete this task by the due date.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to your company",
-    "subject": "Acme portal: [Overdue] Task was due 3 days ago",
+    "subject": "[Overdue] Task was due 3 days ago",
     "title": "View task",
   },
   "DUE_DATE_OVERDUE_7D": {
@@ -30,7 +30,7 @@ Please complete this task as soon as possible.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to your company",
-    "subject": "Acme portal: [Overdue] Task overdue by one week",
+    "subject": "[Overdue] Task overdue by one week",
     "title": "View task",
   },
   "DUE_DATE_TODAY": {
@@ -41,7 +41,7 @@ Please complete this task as soon as possible.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to your company",
-    "subject": "Acme portal: [Due Soon] Task due today",
+    "subject": "[Due Soon] Task due today",
     "title": "View task",
   },
   "NO_DUE_DATE_3D": {
@@ -52,7 +52,7 @@ If you've already completed this task, please mark it as done in the portal.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to your company",
-    "subject": "Acme portal: [Reminder] You have a task to complete",
+    "subject": "[Reminder] You have a task to complete",
     "title": "View task",
   },
   "NO_DUE_DATE_7D": {
@@ -63,7 +63,7 @@ If you've already completed this task, please mark it as done in the portal.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to your company",
-    "subject": "Acme portal: [Reminder] Task still pending",
+    "subject": "[Reminder] Task still pending",
     "title": "View task",
   },
 }
@@ -79,7 +79,7 @@ Please make sure to complete this task by the due date.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to you",
-    "subject": "Acme portal: [Due Soon] Task due in 3 days",
+    "subject": "[Due Soon] Task due in 3 days",
     "title": "View task",
   },
   "DUE_DATE_OVERDUE_3D": {
@@ -88,7 +88,7 @@ Please make sure to complete this task by the due date.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to you",
-    "subject": "Acme portal: [Overdue] Task was due 3 days ago",
+    "subject": "[Overdue] Task was due 3 days ago",
     "title": "View task",
   },
   "DUE_DATE_OVERDUE_7D": {
@@ -99,7 +99,7 @@ Please complete this task as soon as possible.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to you",
-    "subject": "Acme portal: [Overdue] Task overdue by one week",
+    "subject": "[Overdue] Task overdue by one week",
     "title": "View task",
   },
   "DUE_DATE_TODAY": {
@@ -110,7 +110,7 @@ Please complete this task as soon as possible.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to you",
-    "subject": "Acme portal: [Due Soon] Task due today",
+    "subject": "[Due Soon] Task due today",
     "title": "View task",
   },
   "NO_DUE_DATE_3D": {
@@ -121,7 +121,7 @@ If you've already completed this task, please mark it as done in the portal.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to you",
-    "subject": "Acme portal: [Reminder] You have a task to complete",
+    "subject": "[Reminder] You have a task to complete",
     "title": "View task",
   },
   "NO_DUE_DATE_7D": {
@@ -132,7 +132,7 @@ If you've already completed this task, please mark it as done in the portal.",
       "taskId": "task_1",
     },
     "header": "A task was assigned to you",
-    "subject": "Acme portal: [Reminder] Task still pending",
+    "subject": "[Reminder] Task still pending",
     "title": "View task",
   },
 }

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

@@ -39,10 +39,11 @@ describe('getReminderEmailDetails', () => {
     expect(result[TaskReminderType.NO_DUE_DATE_3D].header).toBe('A task was assigned to your team')
   })
 
-  it('falls back gracefully when brandName is missing', () => {
-    const noBrand: WorkspaceResponse = { ...workspace, brandName: undefined }
-    const result = getReminderEmailDetails(noBrand, task, false)
-    expect(result[TaskReminderType.NO_DUE_DATE_3D].subject).toBe('portal: [Reminder] You have a task to complete')
+  it('omits any `<brand> portal:` prefix from subjects (Copilot prepends it server-side)', () => {
+    const result = getReminderEmailDetails(workspace, task, false)
+    for (const variant of Object.values(TaskReminderType)) {
+      expect(result[variant].subject).not.toMatch(/portal:/i)
+    }
   })
 
   it('emits ctaParams with the task id for every variant', () => {

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

@@ -202,16 +202,8 @@ export const getEmailDetails = (
   }
 }
 
-/**
- * Helper function that returns reminder email content for each TaskReminderType variant.
- * Lifecycle is independent from `getEmailDetails` (which is keyed by NotificationTaskActions).
- * @param {WorkspaceResponse} workspace - Workspace whose brandName fronts the subject and
- *   whose labels resolve the company term.
- * @param {Pick<Task, 'id' | 'title'>} task - Task being reminded about. Used for ctaParams and body interpolation.
- * @param {boolean} isCompanyRecipient - True if recipient is a company (header reads "your {groupTerm}"),
- *   false for an individual recipient (header reads "you").
- * @returns Reminder email content keyed by TaskReminderType.
- */
+// 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 = (
   workspace: WorkspaceResponse,
   task: Pick<Task, 'id' | 'title'>,
@@ -226,50 +218,49 @@ export const getReminderEmailDetails = (
     ctaParams: { taskId: string }
   }
 > => {
-  const portalPrefix = `${workspace.brandName ?? ''} portal:`.trimStart()
   const labels = getWorkspaceLabels(workspace)
   const header = isCompanyRecipient ? `A task was assigned to your ${labels.groupTerm}` : 'A task was assigned to you'
   const ctaParams = { taskId: task.id }
   const title = 'View task'
 
   return {
     [TaskReminderType.NO_DUE_DATE_3D]: {
-      subject: `${portalPrefix} [Reminder] You have a task to complete`,
+      subject: '[Reminder] You have a task to complete',
       header,
       title,
       body: `This is a friendly reminder that you have a task ‘${task.title}’ assigned to you that's still pending completion.\n\nIf you've already completed this task, please mark it as done in the portal.`,
       ctaParams,
     },
     [TaskReminderType.NO_DUE_DATE_7D]: {
-      subject: `${portalPrefix} [Reminder] Task still pending`,
+      subject: '[Reminder] Task still pending',
       header,
       title,
       body: `This is a friendly reminder that you have a task ‘${task.title}’ that was assigned to you a week ago and is still pending.\n\nIf you've already completed this task, please mark it as done in the portal.`,
       ctaParams,
     },
     [TaskReminderType.DUE_DATE_BEFORE_3D]: {
-      subject: `${portalPrefix} [Due Soon] Task due in 3 days`,
+      subject: '[Due Soon] Task due in 3 days',
       header,
       title,
       body: `This is a friendly reminder that you have a task ‘${task.title}’ due in 3 days.\n\nPlease make sure to complete this task by the due date.`,
       ctaParams,
     },
     [TaskReminderType.DUE_DATE_TODAY]: {
-      subject: `${portalPrefix} [Due Soon] Task due today`,
+      subject: '[Due Soon] Task due today',
       header,
       title,
       body: `This is a friendly reminder that you have a task ‘${task.title}’ due today.\n\nPlease complete this task as soon as possible.`,
       ctaParams,
     },
     [TaskReminderType.DUE_DATE_OVERDUE_3D]: {
-      subject: `${portalPrefix} [Overdue] Task was due 3 days ago`,
+      subject: '[Overdue] Task was due 3 days ago',
       header,
       title,
       body: `This is a friendly reminder that the task ‘${task.title}’ is now overdue. It was due 3 days ago and is still pending completion.`,
       ctaParams,
     },
     [TaskReminderType.DUE_DATE_OVERDUE_7D]: {
-      subject: `${portalPrefix} [Overdue] Task overdue by one week`,
+      subject: '[Overdue] Task overdue by one week',
       header,
       title,
       body: `This is a friendly reminder that the task ‘${task.title}’ is now one week overdue.\n\nPlease complete this task as soon as possible.`,

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

@@ -0,0 +1,110 @@
+import { TaskReminderType } from '@prisma/client'
+
+const mockSendReminderEmail = jest.fn()
+const mockTaskReminderSentDelete = jest.fn()
+const mockCopilotApiCtor = jest.fn()
+
+jest.mock('@trigger.dev/sdk/v3', () => ({
+  task: ({ run }: { run: (payload: unknown) => unknown }) => ({ run }),
+  tasks: { onFailure: () => undefined },
+  logger: { log: jest.fn(), error: jest.fn(), warn: jest.fn() },
+}))
+
+jest.mock('@/config', () => ({ copilotAPIKey: 'test-api-key' }))
+
+jest.mock('@/lib/db', () => ({
+  __esModule: true,
+  default: {
+    getInstance: () => ({
+      taskReminderSent: { delete: mockTaskReminderSentDelete },
+    }),
+  },
+}))
+
+jest.mock('@/utils/CopilotAPI', () => ({
+  CopilotAPI: jest.fn().mockImplementation((...args: unknown[]) => {
+    mockCopilotApiCtor(...args)
+    return {}
+  }),
+}))
+
+jest.mock('./send-reminder-email', () => ({
+  sendReminderEmail: (...args: unknown[]) => mockSendReminderEmail(...args),
+}))
+
+import {
+  DispatchReminderEmailPayload,
+  dispatchReminderEmailOnFailure,
+  dispatchReminderEmailRun,
+} from './dispatch-reminder-email'
+
+const buildPayload = (overrides: Partial<DispatchReminderEmailPayload> = {}): DispatchReminderEmailPayload => ({
+  ledgerId: 'ledger_1',
+  workspaceId: 'ws_1',
+  task: { id: 'task_1', title: 'Submit timesheet', createdById: 'iu_1' },
+  recipientClientId: 'client_1',
+  recipientCompanyId: 'company_1',
+  reminderType: TaskReminderType.NO_DUE_DATE_3D,
+  isCompanyRecipient: false,
+  workspace: { id: 'ws_1', brandName: 'Acme' },
+  ...overrides,
+})
+
+describe('dispatchReminderEmail', () => {
+  beforeEach(() => {
+    jest.clearAllMocks()
+    mockSendReminderEmail.mockReset()
+    mockTaskReminderSentDelete.mockReset()
+    mockCopilotApiCtor.mockReset()
+  })
+
+  describe('run', () => {
+    it('mints a workspace-scoped CopilotAPI and forwards the payload to sendReminderEmail', async () => {
+      mockSendReminderEmail.mockResolvedValueOnce('notif_1')
+
+      const result = await dispatchReminderEmailRun(buildPayload())
+
+      expect(mockCopilotApiCtor).toHaveBeenCalledWith('', 'ws_1/test-api-key')
+      expect(mockSendReminderEmail).toHaveBeenCalledTimes(1)
+      expect(mockSendReminderEmail.mock.calls[0][0]).toMatchObject({
+        task: { id: 'task_1', title: 'Submit timesheet', createdById: 'iu_1' },
+        recipientClientId: 'client_1',
+        recipientCompanyId: 'company_1',
+        reminderType: TaskReminderType.NO_DUE_DATE_3D,
+        isCompanyRecipient: false,
+      })
+      expect(result).toEqual({ ledgerId: 'ledger_1', notificationId: 'notif_1', sent: true })
+    })
+
+    it('rethrows so Trigger.dev can apply its retry policy', async () => {
+      mockSendReminderEmail.mockRejectedValueOnce(new Error('copilot 5xx'))
+
+      await expect(dispatchReminderEmailRun(buildPayload())).rejects.toThrow('copilot 5xx')
+      expect(mockTaskReminderSentDelete).not.toHaveBeenCalled() // compensation is onFailure's job, not run's
+    })
+  })
+
+  describe('onFailure', () => {
+    it('deletes the ledger row so the next cron run can retry', async () => {
+      mockTaskReminderSentDelete.mockResolvedValueOnce({ id: 'ledger_1' })
+
+      await dispatchReminderEmailOnFailure({
+        payload: buildPayload(),
+        error: new Error('all retries exhausted'),
+      })
+
+      expect(mockTaskReminderSentDelete).toHaveBeenCalledWith({ where: { id: 'ledger_1' } })
+    })
+
+    it('does not throw if the ledger DELETE itself fails (logs and moves on)', async () => {
+      mockTaskReminderSentDelete.mockRejectedValueOnce(new Error('db blew up'))
+
+      await expect(
+        dispatchReminderEmailOnFailure({
+          payload: buildPayload(),
+          error: new Error('all retries exhausted'),
+        }),
+      ).resolves.toBeUndefined()
+    })
+  })
+})

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

@@ -0,0 +1,72 @@
+import 'server-only'
+
+import { copilotAPIKey } from '@/config'
+import DBClient from '@/lib/db'
+import { WorkspaceResponse } from '@/types/common'
+import { CopilotAPI } from '@/utils/CopilotAPI'
+import { serializeError } from '@/utils/serializeError'
+import { Task, TaskReminderType } from '@prisma/client'
+import { logger, task, tasks } from '@trigger.dev/sdk/v3'
+
+import { sendReminderEmail } from './send-reminder-email'
+
+export type DispatchReminderEmailPayload = {
+  ledgerId: string
+  workspaceId: string
+  task: Pick<Task, 'id' | 'title' | 'createdById'>
+  recipientClientId: string
+  recipientCompanyId: string | null
+  reminderType: TaskReminderType
+  isCompanyRecipient: boolean
+  workspace: WorkspaceResponse
+}
+
+const TASK_ID = 'dispatch-reminder-email'
+
+export const dispatchReminderEmailRun = async (payload: DispatchReminderEmailPayload) => {
+  const copilot = new CopilotAPI('', `${payload.workspaceId}/${copilotAPIKey}`)
+  const notificationId = await sendReminderEmail({
+    task: payload.task,
+    recipientClientId: payload.recipientClientId,
+    recipientCompanyId: payload.recipientCompanyId,
+    reminderType: payload.reminderType,
+    isCompanyRecipient: payload.isCompanyRecipient,
+    workspace: payload.workspace,
+    copilot,
+  })
+  return { ledgerId: payload.ledgerId, notificationId, sent: true as const }
+}
+
+// Fires after Trigger.dev exhausts all retries. Compensating here (instead of inside run's
+// catch) avoids dropping the ledger row on transient failures a retry would have recovered.
+// The SDK types the hook's payload as `unknown`; we cast once via destructure.
+export const dispatchReminderEmailOnFailure = async ({ payload, error }: { payload: unknown; error: unknown }) => {
+  const { ledgerId, workspaceId, task, recipientClientId, reminderType } = payload as DispatchReminderEmailPayload
+  logger.error('dispatch-reminder-email: retries exhausted, compensating ledger', {
+    ledgerId,
+    workspaceId,
+    taskId: task.id,
+    recipientClientId,
+    reminderType,
+    error: serializeError(error),
+  })
+  const db = DBClient.getInstance()
+  try {
+    await db.taskReminderSent.delete({ where: { id: ledgerId } })
+  } catch (deleteErr) {
+    logger.error('dispatch-reminder-email: ledger compensation DELETE failed, reminder will not retry', {
+      ledgerId,
+      error: serializeError(deleteErr),
+    })
+  }
+}
+
+export const dispatchReminderEmail = task({
+  id: TASK_ID,
+  queue: { concurrencyLimit: 5 },
+  retry: { maxAttempts: 3, factor: 2, minTimeoutInMs: 1_000, maxTimeoutInMs: 15_000, randomize: true },
+  maxDuration: 30,
+  run: dispatchReminderEmailRun,
+})
+
+tasks.onFailure(TASK_ID, dispatchReminderEmailOnFailure)