fix: skip reminders when scheduled date is in the past (#26942)

* flaky-e2e

* workflow reminder

* remove

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

@@ -1,3 +1,4 @@
+import dayjs from "@calcom/dayjs";
 import { BookingSeatRepository } from "@calcom/features/bookings/repositories/BookingSeatRepository";
 import { EmailWorkflowService } from "@calcom/features/ee/workflows/lib/service/EmailWorkflowService";
 import { WorkflowService } from "@calcom/features/ee/workflows/lib/service/WorkflowService";
@@ -7,7 +8,7 @@ import logger from "@calcom/lib/logger";
 import { getTimeFormatStringFromUserTimeFormat } from "@calcom/lib/timeFormat";
 import prisma from "@calcom/prisma";
 import type { TimeUnit } from "@calcom/prisma/enums";
-import { WorkflowMethods, type WorkflowTemplates, type WorkflowTriggerEvents } from "@calcom/prisma/enums";
+import { WorkflowMethods, WorkflowTriggerEvents, type WorkflowTemplates } from "@calcom/prisma/enums";
 
 import type { BookingInfo, FormSubmissionData, ScheduleEmailReminderAction } from "../types";
 import { sendOrScheduleWorkflowEmails } from "./providers/emailProvider";
@@ -127,6 +128,18 @@ const scheduleEmailReminderForEvt = async (args: scheduleEmailReminderArgs & { e
     timeUnit: timeSpan.timeUnit,
     evt,
   });
+
+  if (
+    scheduledDate &&
+    triggerEvent === WorkflowTriggerEvents.BEFORE_EVENT &&
+    dayjs(scheduledDate).isBefore(dayjs())
+  ) {
+    log.debug(
+      `Skipping reminder for workflow step ${workflowStepId} - scheduled date ${scheduledDate} is in the past`
+    );
+    return;
+  }
+
   const workflowReminderRepository = new WorkflowReminderRepository(prisma);
   const bookingSeatRepository = new BookingSeatRepository(prisma);
   const emailWorkflowService = new EmailWorkflowService(workflowReminderRepository, bookingSeatRepository);

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

@@ -147,6 +147,17 @@ const scheduleSMSReminderForEvt = async (
     scheduledDate = timeSpan.time && timeUnit ? dayjs(endTime).add(timeSpan.time, timeUnit) : null;
   }
 
+  if (
+    scheduledDate &&
+    triggerEvent === WorkflowTriggerEvents.BEFORE_EVENT &&
+    dayjs(scheduledDate).isBefore(dayjs())
+  ) {
+    log.debug(
+      `Skipping reminder for workflow step ${workflowStepId} - scheduled date ${scheduledDate} is in the past`
+    );
+    return;
+  }
+
   const useTwilio = shouldUseTwilio(triggerEvent, scheduledDate);
   if (useTwilio) {
     const attendeeToBeUsedInSMS = getAttendeeToBeUsedInSMS(action, evt, reminderPhone);

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

@@ -77,6 +77,17 @@ export const scheduleWhatsappReminder = async (args: ScheduleTextReminderArgs &
     scheduledDate = timeSpan.time && timeUnit ? dayjs(endTime).add(timeSpan.time, timeUnit) : null;
   }
 
+  if (
+    scheduledDate &&
+    triggerEvent === WorkflowTriggerEvents.BEFORE_EVENT &&
+    dayjs(scheduledDate).isBefore(currentDate)
+  ) {
+    log.debug(
+      `Skipping reminder for workflow step ${workflowStepId} - scheduled date ${scheduledDate} is in the past`
+    );
+    return;
+  }
+
   const name = action === WorkflowActions.WHATSAPP_ATTENDEE ? evt.attendees[0].name : evt.organizer.name;
   const attendeeName =
     action === WorkflowActions.WHATSAPP_ATTENDEE ? evt.organizer.name : evt.attendees[0].name;

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

@@ -1,3 +1,4 @@
+import dayjs from "@calcom/dayjs";
 import { describe, expect, vi, beforeEach } from "vitest";
 
 import { scheduleWorkflowReminders } from "@calcom/features/ee/workflows/lib/reminders/reminderScheduler";
@@ -249,10 +250,14 @@ describe("WorkflowService.scheduleLazyEmailWorkflow", () => {
       timeUnit: TimeUnit.HOUR,
     };
 
+    // Use future dates to ensure scheduled date is not in the past
+    const futureStartTime = dayjs().add(3, "days").toISOString();
+    const futureEndTime = dayjs().add(3, "days").add(1, "hour").toISOString();
+
     const mockEvt = {
       uid: "booking-123",
-      startTime: "2024-12-01T10:00:00Z",
-      endTime: "2024-12-01T11:00:00Z",
+      startTime: futureStartTime,
+      endTime: futureEndTime,
     };
 
     const mockWorkflowReminder = {
@@ -297,10 +302,14 @@ describe("WorkflowService.scheduleLazyEmailWorkflow", () => {
       timeUnit: TimeUnit.HOUR,
     };
 
+    // Use future dates to ensure scheduled date is not in the past
+    const futureStartTime = dayjs().add(1, "day").toISOString();
+    const futureEndTime = dayjs().add(1, "day").add(1, "hour").toISOString();
+
     const mockEvt = {
       uid: "booking-456",
-      startTime: "2024-12-01T10:00:00Z",
-      endTime: "2024-12-01T11:00:00Z",
+      startTime: futureStartTime,
+      endTime: futureEndTime,
     };
 
     const mockWorkflowReminder = {
@@ -337,10 +346,14 @@ describe("WorkflowService.scheduleLazyEmailWorkflow", () => {
       timeUnit: TimeUnit.HOUR,
     };
 
+    // Use future dates to ensure scheduled date is not in the past
+    const futureStartTime = dayjs().add(3, "days").toISOString();
+    const futureEndTime = dayjs().add(3, "days").add(1, "hour").toISOString();
+
     const mockEvt = {
       uid: "booking-789",
-      startTime: "2024-12-01T10:00:00Z",
-      endTime: "2024-12-01T11:00:00Z",
+      startTime: futureStartTime,
+      endTime: futureEndTime,
     };
 
     const mockWorkflowReminder = {
@@ -407,6 +420,71 @@ describe("WorkflowService.scheduleLazyEmailWorkflow", () => {
     expect(mockWorkflowReminderCreate).not.toHaveBeenCalled();
     expect(mockTasker.create).not.toHaveBeenCalled();
   });
+
+  test("should skip reminder if scheduled date is in the past for BEFORE_EVENT", async () => {
+    const mockWorkflow = {
+      time: 48,
+      timeUnit: TimeUnit.HOUR,
+    };
+
+    // Event is only 24 hours away, but reminder is set for 48 hours before
+    // This means the scheduled date would be in the past
+    const tomorrowStartTime = dayjs().add(1, "day").toISOString();
+    const tomorrowEndTime = dayjs().add(1, "day").add(1, "hour").toISOString();
+
+    const mockEvt = {
+      uid: "booking-past-reminder",
+      startTime: tomorrowStartTime,
+      endTime: tomorrowEndTime,
+    };
+
+    await WorkflowService.scheduleLazyEmailWorkflow({
+      workflowTriggerEvent: "BEFORE_EVENT",
+      workflowStepId: 1,
+      workflow: mockWorkflow,
+      evt: mockEvt,
+    });
+
+    // Should not create reminder or schedule task when scheduled date is in the past
+    expect(mockWorkflowReminderCreate).not.toHaveBeenCalled();
+    expect(mockTasker.create).not.toHaveBeenCalled();
+  });
+
+  test("should not skip reminder for AFTER_EVENT even if calculated date seems past", async () => {
+    const mockWorkflow = {
+      time: 1,
+      timeUnit: TimeUnit.HOUR,
+    };
+
+    // For AFTER_EVENT, we add time to endTime, so it should always be in the future
+    const pastStartTime = dayjs().subtract(1, "hour").toISOString();
+    const pastEndTime = dayjs().subtract(30, "minutes").toISOString();
+
+    const mockEvt = {
+      uid: "booking-after-event",
+      startTime: pastStartTime,
+      endTime: pastEndTime,
+    };
+
+    const mockWorkflowReminder = {
+      id: 4,
+      uuid: "reminder-uuid-after",
+    };
+
+    mockWorkflowReminderCreate.mockResolvedValue(mockWorkflowReminder);
+    mockTasker.create.mockResolvedValue({ id: "task-after" });
+
+    await WorkflowService.scheduleLazyEmailWorkflow({
+      workflowTriggerEvent: "AFTER_EVENT",
+      workflowStepId: 4,
+      workflow: mockWorkflow,
+      evt: mockEvt,
+    });
+
+    // AFTER_EVENT reminders should still be scheduled (they're relative to endTime + time)
+    expect(mockWorkflowReminderCreate).toHaveBeenCalled();
+    expect(mockTasker.create).toHaveBeenCalled();
+  });
 });
 
 describe("WorkflowService.processWorkflowScheduledDate", () => {

packages/features/ee/workflows/lib/service/WorkflowService.ts

@@ -281,6 +281,16 @@ export class WorkflowService {
       return;
     }
 
+    if (
+      workflowTriggerEvent === WorkflowTriggerEvents.BEFORE_EVENT &&
+      dayjs(scheduledDate).isBefore(dayjs())
+    ) {
+      log.debug(
+        `Skipping lazy email reminder for workflow step ${workflowStepId} - scheduled date ${scheduledDate} is in the past`
+      );
+      return;
+    }
+
     let workflowReminder: { id: number | null; uuid: string | null };
     try {
       const workflowReminderRepository = new WorkflowReminderRepository(prisma);