diff --git a/packages/features/calAIPhone/providers/retellAI/services/BillingService.ts b/packages/features/calAIPhone/providers/retellAI/services/BillingService.ts
index 79a35d1388a4d8..c0324bfcc71ea3 100644
--- a/packages/features/calAIPhone/providers/retellAI/services/BillingService.ts
+++ b/packages/features/calAIPhone/providers/retellAI/services/BillingService.ts
@@ -1,3 +1,5 @@
+import { z } from "zod";
+
 import { getStripeCustomerIdFromUserId } from "@calcom/app-store/stripepayment/lib/customer";
 import { getPhoneNumberMonthlyPriceId } from "@calcom/app-store/stripepayment/lib/utils";
 import { CHECKOUT_SESSION_TYPES } from "@calcom/features/ee/billing/constants";
@@ -10,6 +12,15 @@ import { PhoneNumberSubscriptionStatus } from "@calcom/prisma/enums";
 import type { PhoneNumberRepositoryInterface } from "../../interfaces/PhoneNumberRepositoryInterface";
 import type { RetellAIRepository } from "../types";
 
+const stripeResourceMissingErrorSchema = z.object({
+  type: z.literal("invalid_request_error"),
+  code: z.literal("resource_missing"),
+  message: z.string(),
+  param: z.string().optional(),
+  doc_url: z.string().optional(),
+  request_log_url: z.string().optional(),
+});
+
 export class BillingService {
   private logger = logger.getSubLogger({ prefix: ["BillingService"] });
 
@@ -129,7 +140,20 @@ export class BillingService {
     }
 
     try {
-      await stripe.subscriptions.cancel(phoneNumber.stripeSubscriptionId);
+      try {
+        await stripe.subscriptions.cancel(phoneNumber.stripeSubscriptionId);
+      } catch (error) {
+        const parsedError = stripeResourceMissingErrorSchema.safeParse(error);
+        if (parsedError.success) {
+          this.logger.info("Subscription not found in Stripe (already cancelled or deleted):", {
+            subscriptionId: phoneNumber.stripeSubscriptionId,
+            phoneNumberId,
+            stripeMessage: parsedError.data.message,
+          });
+        } else {
+          throw error;
+        }
+      }
 
       await this.phoneNumberRepository.updateSubscriptionStatus({
         id: phoneNumberId,
diff --git a/packages/features/calAIPhone/providers/retellAI/services/__tests__/BillingService.test.ts b/packages/features/calAIPhone/providers/retellAI/services/__tests__/BillingService.test.ts
index 3245885fe63541..332de4d1ed761d 100644
--- a/packages/features/calAIPhone/providers/retellAI/services/__tests__/BillingService.test.ts
+++ b/packages/features/calAIPhone/providers/retellAI/services/__tests__/BillingService.test.ts
@@ -254,5 +254,64 @@ describe("BillingService", () => {
         "Failed to cancel subscription"
       );
     });
+
+    it("should handle subscription not found (404) gracefully", async () => {
+      const mockPhoneNumber = createMockPhoneNumberRecord({
+        id: 1,
+        stripeSubscriptionId: "sub_123",
+        subscriptionStatus: PhoneNumberSubscriptionStatus.ACTIVE,
+      });
+
+      mocks.mockPhoneNumberRepository.findByIdAndUserId.mockResolvedValue(mockPhoneNumber);
+      mocks.mockPhoneNumberRepository.updateSubscriptionStatus.mockResolvedValue(undefined);
+      mocks.mockRetellRepository.deletePhoneNumber.mockResolvedValue(undefined);
+
+      const stripe = (await import("@calcom/features/ee/payments/server/stripe")).default;
+      stripe.subscriptions.cancel.mockRejectedValue({
+        type: "invalid_request_error",
+        code: "resource_missing",
+        message: "No such subscription: 'sub_123'",
+        param: "id",
+        doc_url: "https://stripe.com/docs/error-codes/resource-missing",
+      });
+
+      const result = await service.cancelPhoneNumberSubscription(validCancelData);
+
+      expect(result).toEqual({
+        success: true,
+        message: "Phone number subscription cancelled successfully.",
+      });
+
+      // Should attempt to cancel
+      expect(stripe.subscriptions.cancel).toHaveBeenCalledWith("sub_123");
+      // Should still update database even after 404
+      expect(mocks.mockPhoneNumberRepository.updateSubscriptionStatus).toHaveBeenCalledWith({
+        id: 1,
+        subscriptionStatus: PhoneNumberSubscriptionStatus.CANCELLED,
+        disconnectOutboundAgent: true,
+      });
+    });
+
+    it("should throw error on Stripe API failure that is not resource_missing", async () => {
+      const mockPhoneNumber = createMockPhoneNumberRecord({
+        id: 1,
+        stripeSubscriptionId: "sub_123",
+        subscriptionStatus: PhoneNumberSubscriptionStatus.ACTIVE,
+      });
+
+      mocks.mockPhoneNumberRepository.findByIdAndUserId.mockResolvedValue(mockPhoneNumber);
+
+      const stripe = (await import("@calcom/features/ee/payments/server/stripe")).default;
+      stripe.subscriptions.cancel.mockRejectedValue(new TestError("API Error"));
+
+      await expect(service.cancelPhoneNumberSubscription(validCancelData)).rejects.toThrow(
+        "Failed to cancel subscription"
+      );
+
+      // Should attempt to cancel
+      expect(stripe.subscriptions.cancel).toHaveBeenCalledWith("sub_123");
+      // Should NOT update database due to error
+      expect(mocks.mockPhoneNumberRepository.updateSubscriptionStatus).not.toHaveBeenCalled();
+    });
   });
 });