diff --git a/apps/web/src/app/api/stripe/webhook/route.test.ts b/apps/web/src/app/api/stripe/webhook/route.test.ts
new file mode 100644
index 00000000000..b5c7e4bf91d
--- /dev/null
+++ b/apps/web/src/app/api/stripe/webhook/route.test.ts
@@ -0,0 +1,170 @@
+import Stripe from 'stripe';
+import { headers } from 'next/headers';
+import { captureException } from '@sentry/nextjs';
+import { client } from '@kilocode/web-shared/lib/stripe-client';
+import { getEnvVariable } from '@kilocode/web-shared/lib/dotenvx';
+import { processStripePaymentEventHook } from '@/lib/stripe';
+import { POST } from './route';
+
+jest.mock('next/headers', () => ({ headers: jest.fn() }));
+jest.mock('@sentry/nextjs', () => ({ captureException: jest.fn() }));
+jest.mock('@/lib/stripe', () => ({ processStripePaymentEventHook: jest.fn() }));
+jest.mock('@kilocode/web-shared/lib/dotenvx', () => ({
+  getEnvVariable: jest.fn((key: string) =>
+    key === 'STRIPE_WEBHOOK_SECRET' ? 'whsec_local_fixture' : 'local_fixture'
+  ),
+}));
+
+const secret = 'whsec_local_fixture';
+const body = JSON.stringify({
+  id: 'evt_local_fixture',
+  object: 'event',
+  type: 'checkout.session.completed',
+  data: { object: { id: 'cs_local_fixture' } },
+});
+
+function signatureError(): Stripe.errors.StripeSignatureVerificationError {
+  try {
+    client.webhooks.constructEvent(body, 'fixture', secret);
+  } catch (error) {
+    if (error instanceof Stripe.errors.StripeSignatureVerificationError) {
+      return error;
+    }
+    throw error;
+  }
+  throw new Error('Expected SDK verification error');
+}
+
+async function deliver(
+  payload = body,
+  signature: string | null = client.webhooks.generateTestHeaderString({ payload, secret })
+) {
+  jest
+    .mocked(headers)
+    .mockResolvedValue(new Headers(signature === null ? {} : { 'stripe-signature': signature }));
+  return POST(
+    new Request('http://localhost/api/stripe/webhook', { method: 'POST', body: payload })
+  );
+}
+
+describe('Stripe webhook responses', () => {
+  let now = Date.UTC(2026, 0, 1);
+
+  beforeEach(() => {
+    jest.clearAllMocks();
+    now += 60_000;
+    jest.spyOn(Date, 'now').mockImplementation(() => now);
+    jest.mocked(processStripePaymentEventHook).mockResolvedValue(undefined);
+    jest
+      .mocked(getEnvVariable)
+      .mockImplementation((key: string) =>
+        key === 'STRIPE_WEBHOOK_SECRET' ? secret : 'local_fixture'
+      );
+  });
+
+  afterEach(() => {
+    jest.restoreAllMocks();
+  });
+
+  test('refuses a request without a signature header', async () => {
+    const response = await deliver(body, null);
+    expect(response.status).toBe(400);
+    expect(await response.text()).toBe('Webhook Error');
+    expect(processStripePaymentEventHook).not.toHaveBeenCalled();
+    expect(captureException).not.toHaveBeenCalled();
+  });
+
+  test.each([
+    () => 'fixture',
+    () =>
+      client.webhooks.generateTestHeaderString({ payload: body, secret: 'whsec_other_fixture' }),
+    () =>
+      client.webhooks.generateTestHeaderString({
+        payload: body,
+        secret,
+        timestamp: Math.floor(Date.now() / 1000) - 3600,
+      }),
+  ])('refuses and reports a failed signature verification %#', async buildSignature => {
+    const response = await deliver(body, buildSignature());
+    expect(response.status).toBe(400);
+    expect(await response.text()).toBe('Webhook Error');
+    expect(processStripePaymentEventHook).not.toHaveBeenCalled();
+    expect(captureException).toHaveBeenCalledTimes(1);
+
+    const [reported, options] = jest.mocked(captureException).mock.calls[0];
+    expect(reported).toBeInstanceOf(Stripe.errors.StripeSignatureVerificationError);
+    expect(options).toEqual({ tags: { source: 'stripe_webhook_signature' } });
+  });
+
+  test('limits verification reports across failure causes', async () => {
+    await deliver(body, 'fixture');
+    await deliver(
+      body,
+      client.webhooks.generateTestHeaderString({ payload: body, secret: 'whsec_other_fixture' })
+    );
+
+    expect(captureException).toHaveBeenCalledTimes(1);
+
+    now += 60_000;
+    await deliver(
+      body,
+      client.webhooks.generateTestHeaderString({
+        payload: body,
+        secret,
+        timestamp: Math.floor(Date.now() / 1000) - 3600,
+      })
+    );
+
+    expect(captureException).toHaveBeenCalledTimes(2);
+  });
+
+  test('refuses delivery when the signing secret is not configured', async () => {
+    jest
+      .mocked(getEnvVariable)
+      .mockImplementation((key: string) =>
+        key === 'STRIPE_WEBHOOK_SECRET' ? '' : 'local_fixture'
+      );
+    const consoleError = jest.spyOn(console, 'error').mockImplementation(() => {});
+
+    const response = await deliver();
+
+    expect(response.status).toBe(500);
+    expect(await response.text()).toBe('Missing STRIPE_WEBHOOK_SECRET');
+    expect(processStripePaymentEventHook).not.toHaveBeenCalled();
+    expect(captureException).toHaveBeenCalledTimes(1);
+    expect(captureException).toHaveBeenCalledWith(new Error('STRIPE_WEBHOOK_SECRET is not set'));
+    expect(consoleError).toHaveBeenCalledWith('STRIPE_WEBHOOK_SECRET is not set');
+  });
+
+  test('acknowledges event delivery', async () => {
+    const response = await deliver();
+    expect(response.status).toBe(200);
+    expect(await response.text()).toBe('OK');
+    expect(processStripePaymentEventHook).toHaveBeenCalledWith(JSON.parse(body));
+    expect(captureException).not.toHaveBeenCalled();
+  });
+
+  test.each([new Error('local processing failure'), signatureError()])(
+    'retains processing diagnostics %#',
+    async error => {
+      jest.mocked(processStripePaymentEventHook).mockRejectedValueOnce(error);
+      const response = await deliver();
+      expect(response.status).toBe(400);
+      expect(await response.text()).toBe(`Webhook Error: ${error.message}`);
+      expect(captureException).toHaveBeenCalledTimes(1);
+      expect(captureException).toHaveBeenCalledWith(error);
+    }
+  );
+
+  test('retains unexpected diagnostics', async () => {
+    const error = new Error('local verification failure');
+    jest.spyOn(client.webhooks, 'constructEvent').mockImplementationOnce(() => {
+      throw error;
+    });
+    const response = await deliver();
+    expect(response.status).toBe(400);
+    expect(await response.text()).toBe('Webhook Error: local verification failure');
+    expect(captureException).toHaveBeenCalledWith(error);
+    expect(processStripePaymentEventHook).not.toHaveBeenCalled();
+  });
+});
diff --git a/apps/web/src/app/api/stripe/webhook/route.ts b/apps/web/src/app/api/stripe/webhook/route.ts
index 5ff830d069a..e02515048f9 100644
--- a/apps/web/src/app/api/stripe/webhook/route.ts
+++ b/apps/web/src/app/api/stripe/webhook/route.ts
@@ -4,26 +4,51 @@ import { NextResponse } from 'next/server';
 import { processStripePaymentEventHook } from '@/lib/stripe';
 import { captureException } from '@sentry/nextjs';
 import { client } from '@kilocode/web-shared/lib/stripe-client';
+import Stripe from 'stripe';
+
+const SIGNATURE_FAILURE_REPORT_INTERVAL_MS = 60_000;
+
+let lastSignatureFailureReportedAt = 0;
+
+function reportSignatureFailure(error: Stripe.errors.StripeSignatureVerificationError): void {
+  const now = Date.now();
+  if (now - lastSignatureFailureReportedAt < SIGNATURE_FAILURE_REPORT_INTERVAL_MS) {
+    return;
+  }
+  lastSignatureFailureReportedAt = now;
+  captureException(error, { tags: { source: 'stripe_webhook_signature' } });
+}
 
 export async function POST(req: Request): Promise<NextResponse<unknown>> {
   const body = await req.text();
   const signature = (await headers()).get('stripe-signature');
 
   if (!signature) {
-    return new NextResponse('No stripe-signature header found', { status: 400 });
+    return new NextResponse('Webhook Error', { status: 400 });
   }
 
   if (!getEnvVariable('STRIPE_WEBHOOK_SECRET')) {
-    console.error('STRIPE_WEBHOOK_SECRET is not set');
+    const error = new Error('STRIPE_WEBHOOK_SECRET is not set');
+    console.error(error.message);
+    captureException(error);
     return new NextResponse('Missing STRIPE_WEBHOOK_SECRET', { status: 500 });
   }
 
   try {
-    const event = client.webhooks.constructEvent(
-      body,
-      signature,
-      getEnvVariable('STRIPE_WEBHOOK_SECRET')
-    );
+    let event: Stripe.Event;
+    try {
+      event = client.webhooks.constructEvent(
+        body,
+        signature,
+        getEnvVariable('STRIPE_WEBHOOK_SECRET')
+      );
+    } catch (err: unknown) {
+      if (err instanceof Stripe.errors.StripeSignatureVerificationError) {
+        reportSignatureFailure(err);
+        return new NextResponse('Webhook Error', { status: 400 });
+      }
+      throw err;
+    }
     await processStripePaymentEventHook(event);
   } catch (err: unknown) {
     const errorMessage = err instanceof Error ? err.message : 'Unknown error';