feat: add feature flag for sending workflow emails with smtp (#21187)

* add feature flag

* add unit tests

---------

Co-authored-by: CarinaWolli <wollencarina@gmail.com>

packages/features/ee/round-robin/roundRobinManualReassignment.ts

@@ -423,6 +423,8 @@ async function handleWorkflowsUpdate({
           template: true,
           workflow: {
             select: {
+              userId: true,
+              teamId: true,
               trigger: true,
               time: true,
               timeUnit: true,
@@ -468,6 +470,8 @@ async function handleWorkflowsUpdate({
         includeCalendarEvent: workflowStep.includeCalendarEvent,
         workflowStepId: workflowStep.id,
         verifiedAt: workflowStep.verifiedAt,
+        userId: workflow.userId,
+        teamId: workflow.teamId,
       });
     }
 

packages/features/ee/round-robin/roundRobinReassignment.ts

@@ -460,6 +460,8 @@ export const roundRobinReassignment = async ({
             template: true,
             workflow: {
               select: {
+                userId: true,
+                teamId: true,
                 trigger: true,
                 time: true,
                 timeUnit: true,
@@ -506,6 +508,8 @@ export const roundRobinReassignment = async ({
           includeCalendarEvent: workflowStep.includeCalendarEvent,
           workflowStepId: workflowStep.id,
           verifiedAt: workflowStep.verifiedAt,
+          userId: workflow.userId,
+          teamId: workflow.teamId,
         });
       }
 

packages/features/ee/workflows/api/scheduleEmailReminders.ts

@@ -40,7 +40,7 @@ export async function handler(req: NextRequest) {
     return NextResponse.json({ message: "Not authenticated" }, { status: 401 });
   }
 
-  const isSendgridEnabled = process.env.SENDGRID_API_KEY && process.env.SENDGRID_EMAIL;
+  const isSendgridEnabled = !!(process.env.SENDGRID_API_KEY && process.env.SENDGRID_EMAIL);
 
   if (isSendgridEnabled) {
     const remindersToDelete: { referenceId: string | null; id: number }[] = await getAllRemindersToDelete();
@@ -65,9 +65,7 @@ export async function handler(req: NextRequest) {
     });
 
     await Promise.allSettled(handlePastCancelledReminders);
-  }
 
-  if (isSendgridEnabled) {
     //cancel reminders for cancelled/rescheduled bookings that are scheduled within the next hour
     const remindersToCancel: { referenceId: string | null; id: number }[] = await getAllRemindersToCancel();
 

packages/features/ee/workflows/lib/reminders/emailReminderManager.ts

@@ -3,6 +3,7 @@ import { v4 as uuidv4 } from "uuid";
 
 import dayjs from "@calcom/dayjs";
 import generateIcsString from "@calcom/emails/lib/generateIcsString";
+import { FeaturesRepository } from "@calcom/features/flags/features.repository";
 import { preprocessNameFieldDataWithVariant } from "@calcom/features/form-builder/utils";
 import tasker from "@calcom/features/tasker";
 import { WEBSITE_URL } from "@calcom/lib/constants";
@@ -50,6 +51,8 @@ interface scheduleEmailReminderArgs extends ScheduleReminderArgs {
   evt: BookingInfo;
   sendTo: string[];
   action: ScheduleEmailReminderAction;
+  userId?: number | null;
+  teamId?: number | null;
   emailSubject?: string;
   emailBody?: string;
   hideBranding?: boolean;
@@ -75,6 +78,8 @@ export const scheduleEmailReminder = async (args: scheduleEmailReminderArgs) =>
     isMandatoryReminder,
     action,
     verifiedAt,
+    userId,
+    teamId,
   } = args;
 
   if (!verifiedAt) {
@@ -259,9 +264,17 @@ export const scheduleEmailReminder = async (args: scheduleEmailReminderArgs) =>
 
   const mailData = await prepareEmailData();
 
-  const isSendgridEnabled = process.env.SENDGRID_API_KEY && process.env.SENDGRID_EMAIL;
+  const isSendgridEnabled = !!(process.env.SENDGRID_API_KEY && process.env.SENDGRID_EMAIL);
 
-  if (!isSendgridEnabled) {
+  const featureRepo = new FeaturesRepository();
+
+  const isWorkflowSmtpEmailsEnabled = teamId
+    ? await featureRepo.checkIfTeamHasFeature(teamId, "workflow-smtp-emails")
+    : userId
+    ? await featureRepo.checkIfUserHasFeature(userId, "workflow-smtp-emails")
+    : false;
+
+  if (isWorkflowSmtpEmailsEnabled || !isSendgridEnabled) {
     let reminderUid;
     if (scheduledDate) {
       const reminder = await prisma.workflowReminder.create({

packages/features/ee/workflows/lib/reminders/reminderScheduler.ts

@@ -151,6 +151,8 @@ const processWorkflowStep = async (
       seatReferenceUid,
       includeCalendarEvent: step.includeCalendarEvent,
       verifiedAt: step.verifiedAt,
+      userId: workflow.userId,
+      teamId: workflow.teamId,
     });
   } else if (isWhatsappAction(step.action)) {
     const sendTo = step.action === WorkflowActions.WHATSAPP_ATTENDEE ? smsReminderNumber : step.sendTo;

packages/features/ee/workflows/lib/reminders/scheduleMandatoryReminder.ts

@@ -65,6 +65,7 @@ export async function scheduleMandatoryReminder({
           isMandatoryReminder: true,
           // Template is fixed so we don't have to verify
           verifiedAt: new Date(),
+          userId: evt.organizer.id,
         });
       } catch (error) {
         log.error("Error while scheduling mandatory reminders", JSON.stringify({ error }));

packages/features/ee/workflows/lib/test/workflows.test.ts

@@ -13,10 +13,16 @@ import {
 } from "@calcom/web/test/utils/bookingScenario/expects";
 import { setupAndTeardown } from "@calcom/web/test/utils/bookingScenario/setupAndTeardown";
 
-import { describe, expect, beforeAll, vi } from "vitest";
+import { describe, expect, beforeAll, vi, beforeEach } from "vitest";
 
 import dayjs from "@calcom/dayjs";
-import { BookingStatus, WorkflowMethods, TimeUnit } from "@calcom/prisma/enums";
+import {
+  BookingStatus,
+  WorkflowMethods,
+  TimeUnit,
+  WorkflowTriggerEvents,
+  WorkflowActions,
+} from "@calcom/prisma/enums";
 import {
   deleteRemindersOfActiveOnIds,
   scheduleBookingReminders,
@@ -24,7 +30,11 @@ import {
 } from "@calcom/trpc/server/routers/viewer/workflows/util";
 import { test } from "@calcom/web/test/fixtures/fixtures";
 
+import { FeaturesRepository } from "../../../../flags/features.repository";
 import { deleteWorkfowRemindersOfRemovedMember } from "../../../teams/lib/deleteWorkflowRemindersOfRemovedMember";
+import { scheduleEmailReminder } from "../reminders/emailReminderManager";
+import * as emailProvider from "../reminders/providers/emailProvider";
+import * as sendgridProvider from "../reminders/providers/sendgridProvider";
 
 const workflowSelect = {
   id: true,
@@ -949,3 +959,114 @@ describe("deleteWorkfowRemindersOfRemovedMember", () => {
     );
   });
 });
+
+describe("Workflow SMTP Emails Feature Flag", () => {
+  vi.spyOn(sendgridProvider, "sendSendgridMail");
+  vi.spyOn(emailProvider, "sendOrScheduleWorkflowEmails");
+
+  const mockEvt = {
+    uid: "test-uid",
+    title: "Test Event",
+    startTime: new Date().toISOString(),
+    endTime: new Date().toISOString(),
+    bookerUrl: "https://cal.com",
+    attendees: [
+      {
+        name: "Test Attendee",
+        email: "attendee@test.com",
+        timeZone: "UTC",
+        language: { locale: "en" },
+      },
+    ],
+    organizer: {
+      name: "Test Organizer",
+      email: "organizer@test.com",
+      timeZone: "UTC",
+      language: { locale: "en" },
+    },
+  };
+
+  const baseArgs = {
+    evt: mockEvt,
+    triggerEvent: WorkflowTriggerEvents.NEW_EVENT,
+    timeSpan: { time: 1, timeUnit: TimeUnit.HOUR },
+    sendTo: ["test@example.com"],
+    action: WorkflowActions.EMAIL_ATTENDEE,
+    verifiedAt: new Date(),
+  };
+
+  beforeEach(() => {
+    vi.clearAllMocks();
+    // Mock SendGrid environment variables
+    process.env.SENDGRID_API_KEY = "test-key";
+    process.env.SENDGRID_EMAIL = "test@example.com";
+  });
+
+  test("should use SMTP when team has workflow-smtp-emails feature", async () => {
+    const featuresRepository = new FeaturesRepository();
+    vi.spyOn(FeaturesRepository.prototype, "checkIfTeamHasFeature").mockResolvedValue(true);
+
+    await scheduleEmailReminder({
+      ...baseArgs,
+      teamId: 123,
+    });
+    expect(sendgridProvider.sendSendgridMail).not.toHaveBeenCalled();
+    expect(emailProvider.sendOrScheduleWorkflowEmails).toHaveBeenCalled();
+  });
+
+  test("should use SMTP when user has workflow-smtp-emails feature", async () => {
+    const featuresRepository = new FeaturesRepository();
+    vi.spyOn(FeaturesRepository.prototype, "checkIfUserHasFeature").mockResolvedValue(true);
+
+    await scheduleEmailReminder({
+      ...baseArgs,
+      userId: 123,
+    });
+    expect(sendgridProvider.sendSendgridMail).not.toHaveBeenCalled();
+    expect(emailProvider.sendOrScheduleWorkflowEmails).toHaveBeenCalled();
+  });
+
+  test("should use SendGrid when workflow-smtp-emails feature is not enabled for team", async () => {
+    const featuresRepository = new FeaturesRepository();
+    vi.spyOn(FeaturesRepository.prototype, "checkIfTeamHasFeature").mockResolvedValue(false);
+
+    await scheduleEmailReminder({
+      ...baseArgs,
+      teamId: 123,
+    });
+
+    expect(sendgridProvider.sendSendgridMail).toHaveBeenCalled();
+    expect(emailProvider.sendOrScheduleWorkflowEmails).not.toHaveBeenCalled();
+  });
+
+  test("should use SendGrid when workflow-smtp-emails feature is not enabled for user", async () => {
+    const featuresRepository = new FeaturesRepository();
+    vi.spyOn(FeaturesRepository.prototype, "checkIfUserHasFeature").mockResolvedValue(false);
+
+    await scheduleEmailReminder({
+      ...baseArgs,
+      userId: 123,
+    });
+
+    expect(sendgridProvider.sendSendgridMail).toHaveBeenCalled();
+    expect(emailProvider.sendOrScheduleWorkflowEmails).not.toHaveBeenCalled();
+  });
+
+  test("should use SMTP when SendGrid is not configured", async () => {
+    const featuresRepository = new FeaturesRepository();
+    vi.spyOn(featuresRepository, "checkIfTeamHasFeature").mockResolvedValue(false);
+    vi.spyOn(featuresRepository, "checkIfUserHasFeature").mockResolvedValue(false);
+
+    delete process.env.SENDGRID_API_KEY;
+    delete process.env.SENDGRID_EMAIL;
+
+    await scheduleEmailReminder({
+      ...baseArgs,
+      teamId: 123,
+      userId: 456,
+    });
+
+    expect(sendgridProvider.sendSendgridMail).not.toHaveBeenCalled();
+    expect(emailProvider.sendOrScheduleWorkflowEmails).toHaveBeenCalled();
+  });
+});

packages/features/flags/config.ts

@@ -18,5 +18,6 @@ export type AppFlags = {
   "organizer-request-email-v2": boolean;
   "delegation-credential": boolean;
   "salesforce-crm-tasker": boolean;
+  "workflow-smtp-emails": boolean;
   "cal-video-log-in-overlay": boolean;
 };

packages/features/flags/hooks/index.ts

@@ -17,6 +17,7 @@ const initialData: AppFlags = {
   "organizer-request-email-v2": false,
   "delegation-credential": false,
   "salesforce-crm-tasker": false,
+  "workflow-smtp-emails": false,
   "cal-video-log-in-overlay": false,
 };
 

packages/prisma/migrations/20250508131736_add_workflow_smtp_feature_flag/migration.sql

@@ -0,0 +1,9 @@
+INSERT INTO
+  "Feature" (slug, enabled, description, "type")
+VALUES
+  (
+    'workflow-smtp-emails',
+    false,
+    'Whether to use SMTP for workflow emails or SendGrid on a team/user basis.',
+    'OPERATIONAL'
+  ) ON CONFLICT (slug) DO NOTHING;

packages/trpc/server/routers/viewer/workflows/activateEventType.handler.ts

@@ -314,6 +314,8 @@ export const activateEventTypeHandler = async ({ ctx, input }: ActivateEventType
               sender: step.sender,
               workflowStepId: step.id,
               verifiedAt: step.verifiedAt,
+              userId: eventTypeWorkflow.userId,
+              teamId: eventTypeWorkflow.teamId,
             });
           } else if (step.action === WorkflowActions.SMS_NUMBER && step.sendTo) {
             await scheduleSMSReminder({

packages/trpc/server/routers/viewer/workflows/util.ts

@@ -704,6 +704,8 @@ export async function scheduleBookingReminders(
           sender: step.sender,
           workflowStepId: step.id,
           verifiedAt: step?.verifiedAt ?? null,
+          userId,
+          teamId,
         });
       } else if (step.action === WorkflowActions.SMS_NUMBER && step.sendTo) {
         await scheduleSMSReminder({