diff --git a/packages/features/ee/billing/api/webhook/_customer.subscription.updated.ts b/packages/features/ee/billing/api/webhook/_customer.subscription.updated.ts
index e167880e7f..8b556ed6bb 100644
--- a/packages/features/ee/billing/api/webhook/_customer.subscription.updated.ts
+++ b/packages/features/ee/billing/api/webhook/_customer.subscription.updated.ts
@@ -5,6 +5,7 @@ import { PrismaTeamBillingRepository } from "@calcom/features/ee/billing/reposit
 import { extractBillingDataFromStripeSubscription } from "@calcom/features/ee/billing/lib/stripe-subscription-utils";
 import logger from "@calcom/lib/logger";
 import prisma from "@calcom/prisma";
+
 import { PhoneNumberSubscriptionStatus } from "@calcom/prisma/enums";
 
 const log = logger.getSubLogger({ prefix: ["subscription-updated-webhook"] });
@@ -31,7 +32,10 @@ const handler = async (data: Data) => {
     ? await handleCalAIPhoneNumberSubscriptionUpdate(subscription, phoneNumber)
     : null;
 
-  const teamBillingResult = await handleTeamBillingRenewal(subscription, previousAttributes);
+  const teamBillingResult = await handleTeamBillingRenewal(
+    subscription,
+    previousAttributes
+  );
 
   return {
     phoneNumber: phoneNumberResult,
@@ -57,7 +61,8 @@ async function handleCalAIPhoneNumberSubscriptionUpdate(
     paused: PhoneNumberSubscriptionStatus.CANCELLED,
   };
 
-  const subscriptionStatus = statusMap[subscription.status] || PhoneNumberSubscriptionStatus.UNPAID;
+  const subscriptionStatus =
+    statusMap[subscription.status] || PhoneNumberSubscriptionStatus.UNPAID;
 
   await prisma.calAiPhoneNumber.update({
     where: {
@@ -68,7 +73,11 @@ async function handleCalAIPhoneNumberSubscriptionUpdate(
     },
   });
 
-  return { success: true, subscriptionId: subscription.id, status: subscriptionStatus };
+  return {
+    success: true,
+    subscriptionId: subscription.id,
+    status: subscriptionStatus,
+  };
 }
 
 async function handleTeamBillingRenewal(
@@ -83,7 +92,8 @@ async function handleTeamBillingRenewal(
   const { subscriptionStart, subscriptionEnd, subscriptionTrialEnd } =
     billingProviderService.extractSubscriptionDates(subscription);
 
-  const { billingPeriod, pricePerSeat, paidSeats } = extractBillingDataFromStripeSubscription(subscription);
+  const { billingPeriod, pricePerSeat, paidSeats } =
+    extractBillingDataFromStripeSubscription(subscription);
 
   const teamBillingRepo = new PrismaTeamBillingRepository(prisma);
   const orgBillingRepo = new PrismaOrganizationBillingRepository(prisma);
@@ -97,7 +107,9 @@ async function handleTeamBillingRenewal(
     pricePerSeat: pricePerSeat ?? null,
   };
 
-  const teamBilling = await teamBillingRepo.findBySubscriptionId(subscription.id);
+  const teamBilling = await teamBillingRepo.findBySubscriptionId(
+    subscription.id
+  );
 
   if (teamBilling) {
     await teamBillingRepo.updateById(teamBilling.id, billingUpdateData);
@@ -113,7 +125,10 @@ async function handleTeamBillingRenewal(
 
   log.warn("Subscription renewal received but no billing record found", {
     subscriptionId: subscription.id,
-    customerId: typeof subscription.customer === "string" ? subscription.customer : subscription.customer?.id,
+    customerId:
+      typeof subscription.customer === "string"
+        ? subscription.customer
+        : subscription.customer?.id,
   });
 
   return { skipped: true, reason: "no billing record found" };
diff --git a/packages/features/ee/billing/lib/month-key.ts b/packages/features/ee/billing/lib/month-key.ts
index fff73a3406..8fb22b7d82 100644
--- a/packages/features/ee/billing/lib/month-key.ts
+++ b/packages/features/ee/billing/lib/month-key.ts
@@ -3,3 +3,9 @@ export function formatMonthKey(date: Date): string {
   const month = String(date.getUTCMonth() + 1).padStart(2, "0");
   return `${year}-${month}`;
 }
+
+const MONTH_KEY_REGEX = /^\d{4}-(0[1-9]|1[0-2])$/;
+
+export function isValidMonthKey(value: string): boolean {
+  return MONTH_KEY_REGEX.test(value);
+}
diff --git a/packages/features/ee/billing/service/proration/__tests__/MonthlyProrationService.integration-test.ts b/packages/features/ee/billing/service/proration/__tests__/MonthlyProrationService.integration-test.ts
index ac36ce508d..cbbc22677e 100644
--- a/packages/features/ee/billing/service/proration/__tests__/MonthlyProrationService.integration-test.ts
+++ b/packages/features/ee/billing/service/proration/__tests__/MonthlyProrationService.integration-test.ts
@@ -11,13 +11,19 @@ import { SeatChangeTrackingService } from "../../seatTracking/SeatChangeTracking
 import { MonthlyProrationService } from "../MonthlyProrationService";
 
 const mockBillingService: IBillingProviderService = {
-  createInvoiceItem: vi.fn().mockResolvedValue({ invoiceItemId: "ii_test_123" }),
+  createInvoiceItem: vi
+    .fn()
+    .mockResolvedValue({ invoiceItemId: "ii_test_123" }),
   deleteInvoiceItem: vi.fn().mockResolvedValue(undefined),
   createInvoice: vi.fn().mockResolvedValue({ invoiceId: "in_test_123" }),
   finalizeInvoice: vi.fn().mockResolvedValue(undefined),
   getSubscription: vi.fn().mockResolvedValue({
     items: [
-      { id: "si_test_123", quantity: 1, price: { unit_amount: 12000, recurring: { interval: "year" } } },
+      {
+        id: "si_test_123",
+        quantity: 1,
+        price: { unit_amount: 12000, recurring: { interval: "year" } },
+      },
     ],
     customer: "cus_test_123",
     status: "active",
@@ -31,11 +37,18 @@ const mockBillingService: IBillingProviderService = {
   handleSubscriptionCancel: vi.fn().mockResolvedValue(undefined),
   handleSubscriptionCreation: vi.fn().mockResolvedValue(undefined),
   handleEndTrial: vi.fn().mockResolvedValue(undefined),
-  createCustomer: vi.fn().mockResolvedValue({ stripeCustomerId: "cus_test_123" }),
-  createPaymentIntent: vi.fn().mockResolvedValue({ id: "pi_test_123", client_secret: "secret_123" }),
+  createCustomer: vi
+    .fn()
+    .mockResolvedValue({ stripeCustomerId: "cus_test_123" }),
+  createPaymentIntent: vi
+    .fn()
+    .mockResolvedValue({ id: "pi_test_123", client_secret: "secret_123" }),
   createSubscriptionCheckout: vi
     .fn()
-    .mockResolvedValue({ checkoutUrl: "https://checkout.test", sessionId: "cs_test_123" }),
+    .mockResolvedValue({
+      checkoutUrl: "https://checkout.test",
+      sessionId: "cs_test_123",
+    }),
   createPrice: vi.fn().mockResolvedValue({ priceId: "price_test_123" }),
   getPrice: vi.fn().mockResolvedValue(null),
   getSubscriptionStatus: vi.fn().mockResolvedValue(null),
@@ -131,7 +144,10 @@ describe("MonthlyProrationService Integration Tests", () => {
   });
 
   it("should process end-to-end proration for annual team with seat additions", async () => {
-    const prorationService = new MonthlyProrationService(undefined, mockBillingService);
+    const prorationService = new MonthlyProrationService(
+      undefined,
+      mockBillingService
+    );
     const timestamp = Date.now();
     const randomSuffix = Math.random().toString(36).substring(7);
 
@@ -201,12 +217,17 @@ describe("MonthlyProrationService Integration Tests", () => {
     });
 
     expect(seatChanges).toHaveLength(2);
-    expect(seatChanges.every((sc) => sc.processedInProrationId === proration?.id)).toBe(true);
+    expect(
+      seatChanges.every((sc) => sc.processedInProrationId === proration?.id)
+    ).toBe(true);
   });
 
   it("should create a $0 proration for team with no net change", async () => {
     const seatTracker = new SeatChangeTrackingService();
-    const prorationService = new MonthlyProrationService(undefined, mockBillingService);
+    const prorationService = new MonthlyProrationService(
+      undefined,
+      mockBillingService
+    );
 
     await seatTracker.logSeatAddition({
       teamId: testTeam.id,
@@ -301,16 +322,25 @@ describe("MonthlyProrationService Integration Tests", () => {
       featuresRepository: mockFeaturesRepository,
       billingService: mockBillingService,
     });
-    const results = await prorationService.processMonthlyProrations({ monthKey });
+    const results = await prorationService.processMonthlyProrations({
+      monthKey,
+    });
 
-    const filteredResults = results.filter((r) => [testTeam.id, testTeam2.id].includes(r.teamId));
+    const filteredResults = results.filter((r) =>
+      [testTeam.id, testTeam2.id].includes(r.teamId)
+    );
     expect(filteredResults).toHaveLength(2);
-    expect(filteredResults.every((r) => r.status === "INVOICE_CREATED")).toBe(true);
+    expect(filteredResults.every((r) => r.status === "INVOICE_CREATED")).toBe(
+      true
+    );
   });
 
   it("should handle payment success callback", async () => {
     const seatTracker = new SeatChangeTrackingService();
-    const prorationService = new MonthlyProrationService(undefined, mockBillingService);
+    const prorationService = new MonthlyProrationService(
+      undefined,
+      mockBillingService
+    );
 
     await seatTracker.logSeatAddition({
       teamId: testTeam.id,
@@ -338,7 +368,10 @@ describe("MonthlyProrationService Integration Tests", () => {
 
   it("should handle payment failure callback", async () => {
     const seatTracker = new SeatChangeTrackingService();
-    const prorationService = new MonthlyProrationService(undefined, mockBillingService);
+    const prorationService = new MonthlyProrationService(
+      undefined,
+      mockBillingService
+    );
 
     await seatTracker.logSeatAddition({
       teamId: testTeam.id,
@@ -369,7 +402,10 @@ describe("MonthlyProrationService Integration Tests", () => {
 
   it("should call handleSubscriptionUpdate when updating subscription quantity", async () => {
     const seatTracker = new SeatChangeTrackingService();
-    const prorationService = new MonthlyProrationService(undefined, mockBillingService);
+    const prorationService = new MonthlyProrationService(
+      undefined,
+      mockBillingService
+    );
 
     // Reset the mock to track calls
     vi.mocked(mockBillingService.handleSubscriptionUpdate).mockClear();
@@ -403,9 +439,14 @@ describe("MonthlyProrationService Integration Tests", () => {
     const seatTracker = new SeatChangeTrackingService();
     const failingBillingService = {
       ...mockBillingService,
-      handleSubscriptionUpdate: vi.fn().mockRejectedValue(new Error("Subscription not found")),
+      handleSubscriptionUpdate: vi
+        .fn()
+        .mockRejectedValue(new Error("Subscription not found")),
     };
-    const prorationService = new MonthlyProrationService(undefined, failingBillingService);
+    const prorationService = new MonthlyProrationService(
+      undefined,
+      failingBillingService
+    );
 
     await seatTracker.logSeatAddition({
       teamId: testTeam.id,
@@ -420,8 +461,8 @@ describe("MonthlyProrationService Integration Tests", () => {
     });
 
     // Should throw when trying to update subscription
-    await expect(prorationService.handleProrationPaymentSuccess(proration!.id)).rejects.toThrow(
-      "Subscription not found"
-    );
+    await expect(
+      prorationService.handleProrationPaymentSuccess(proration!.id)
+    ).rejects.toThrow("Subscription not found");
   });
 });
diff --git a/packages/features/ee/billing/service/proration/tasker/trigger/processMonthlyProrationBatch.ts b/packages/features/ee/billing/service/proration/tasker/trigger/processMonthlyProrationBatch.ts
index 94f9546844..ab5ab8ae44 100644
--- a/packages/features/ee/billing/service/proration/tasker/trigger/processMonthlyProrationBatch.ts
+++ b/packages/features/ee/billing/service/proration/tasker/trigger/processMonthlyProrationBatch.ts
@@ -14,7 +14,7 @@ export const processMonthlyProrationBatch = schemaTask({
 
     const prorationService = getMonthlyProrationService();
 
-    await prorationService.processMonthlyProrations({
+    return await prorationService.processMonthlyProrations({
       monthKey: payload.monthKey,
       teamIds: payload.teamIds,
     });
diff --git a/packages/features/ee/billing/service/proration/tasker/trigger/scheduleMonthlyProration.ts b/packages/features/ee/billing/service/proration/tasker/trigger/scheduleMonthlyProration.ts
new file mode 100644
index 0000000000..7584bba949
--- /dev/null
+++ b/packages/features/ee/billing/service/proration/tasker/trigger/scheduleMonthlyProration.ts
@@ -0,0 +1,92 @@
+import { schedules } from "@trigger.dev/sdk";
+
+import { monthlyProrationTaskConfig } from "./config";
+
+export const scheduleMonthlyProration = schedules.task({
+  id: "billing.monthly-proration.schedule",
+  ...monthlyProrationTaskConfig,
+  cron: {
+    pattern: "0 0 1 * *",
+    timezone: "UTC",
+  },
+  run: async (payload) => {
+    const { subMonths } = await import("date-fns");
+    const { TriggerDevLogger } = await import("@calcom/lib/triggerDevLogger");
+    const { formatMonthKey, isValidMonthKey } = await import(
+      "@calcom/features/ee/billing/lib/month-key"
+    );
+    const { MonthlyProrationTeamRepository } = await import(
+      "@calcom/features/ee/billing/repository/proration/MonthlyProrationTeamRepository"
+    );
+    const { getFeaturesRepository } = await import(
+      "@calcom/features/di/containers/FeaturesRepository"
+    );
+    const { processMonthlyProrationBatch } = await import(
+      "./processMonthlyProrationBatch"
+    );
+
+    const triggerDevLogger = new TriggerDevLogger();
+    const log = triggerDevLogger.getSubLogger({
+      name: "MonthlyProrationSchedule",
+    });
+
+    const featuresRepository = getFeaturesRepository();
+    const isEnabled = await featuresRepository.checkIfFeatureIsEnabledGlobally(
+      "monthly-proration"
+    );
+
+    if (!isEnabled) {
+      log.info("Monthly proration feature is disabled");
+      return { status: "disabled" };
+    }
+
+    const externalIdMonthKey =
+      payload.externalId && isValidMonthKey(payload.externalId)
+        ? payload.externalId
+        : null;
+
+    let monthKey: string;
+    if (externalIdMonthKey) {
+      monthKey = externalIdMonthKey;
+      log.info(`Using monthKey from externalId: ${monthKey}`);
+    } else {
+      const now = new Date();
+      const startOfCurrentMonthUtc = new Date(
+        Date.UTC(now.getUTCFullYear(), now.getUTCMonth(), 1)
+      );
+      const previousMonthUtc = subMonths(startOfCurrentMonthUtc, 1);
+      monthKey = formatMonthKey(previousMonthUtc);
+    }
+
+    log.info(`Scheduling monthly proration tasks for ${monthKey}`);
+
+    const teamRepository = new MonthlyProrationTeamRepository();
+    const teamIdsList = await teamRepository.getAnnualTeamsWithSeatChanges(
+      monthKey
+    );
+
+    if (teamIdsList.length === 0) {
+      log.info(`No teams with seat changes found for ${monthKey}`);
+      return {
+        monthKey,
+        scheduledTasks: 0,
+      };
+    }
+
+    log.info(`Scheduling ${teamIdsList.length} tasks for ${monthKey}`);
+
+    await processMonthlyProrationBatch.batchTrigger(
+      teamIdsList.map((teamId) => ({
+        payload: {
+          monthKey,
+          teamIds: [teamId],
+        },
+      }))
+    );
+
+    return {
+      monthKey,
+      scheduledTasks: teamIdsList.length,
+    };
+  },
+});