diff --git a/src/commands/webhooks/listen.ts b/src/commands/webhooks/listen.ts
index f71ba161..7f60599a 100644
--- a/src/commands/webhooks/listen.ts
+++ b/src/commands/webhooks/listen.ts
@@ -14,10 +14,13 @@ import { outputError } from '../../lib/output';
 import { requireText } from '../../lib/prompts';
 import { createSpinner } from '../../lib/spinner';
 import { isInteractive } from '../../lib/tty';
+import { resolveUpstream } from './resolve-upstream';
 import { ALL_WEBHOOK_EVENTS, normalizeEvents } from './utils';
 
 const SVIX_HEADERS = ['svix-id', 'svix-timestamp', 'svix-signature'];
 
+const FORWARD_TIMEOUT_MS = 30_000;
+
 function timestamp(): string {
   return new Date().toLocaleTimeString('en-GB', { hour12: false });
 }
@@ -95,6 +98,7 @@ async function forwardPayload(
     method: 'POST',
     headers: forwardHeaders,
     body: rawBody,
+    signal: AbortSignal.timeout(FORWARD_TIMEOUT_MS),
   });
   return { status: resp.status };
 }
@@ -223,6 +227,26 @@ For example, if using ngrok: ngrok http 4318`,
 
         const { type, resourceId, detail } = summarizeEvent(body);
 
+        let forwardResult:
+          | { readonly status: number }
+          | { readonly error: string }
+          | undefined;
+
+        if (opts.forwardTo) {
+          try {
+            const { status } = await forwardPayload(
+              opts.forwardTo,
+              rawBody,
+              svixHeaders,
+            );
+            forwardResult = { status };
+          } catch (err) {
+            forwardResult = {
+              error: err instanceof Error ? err.message : 'Unknown error',
+            };
+          }
+        }
+
         if (jsonMode) {
           const entry: Record<string, unknown> = {
             timestamp: new Date().toISOString(),
@@ -231,20 +255,11 @@ For example, if using ngrok: ngrok http 4318`,
             payload: body,
           };
 
-          if (opts.forwardTo) {
-            try {
-              const { status } = await forwardPayload(
-                opts.forwardTo,
-                rawBody,
-                svixHeaders,
-              );
-              entry.forwarded = { url: opts.forwardTo, status };
-            } catch (err) {
-              entry.forwarded = {
-                url: opts.forwardTo,
-                error: err instanceof Error ? err.message : 'Unknown error',
-              };
-            }
+          if (opts.forwardTo && forwardResult) {
+            entry.forwarded =
+              'error' in forwardResult
+                ? { url: opts.forwardTo, error: forwardResult.error }
+                : { url: opts.forwardTo, status: forwardResult.status };
           }
 
           console.log(JSON.stringify(entry));
@@ -256,29 +271,24 @@ For example, if using ngrok: ngrok http 4318`,
             `${ts} ${pc.bold(typePad)} ${pc.cyan(idPad)} ${detail}\n`,
           );
 
-          if (opts.forwardTo) {
+          if (opts.forwardTo && forwardResult) {
             const target = opts.forwardTo.startsWith('http')
               ? opts.forwardTo
               : `http://${opts.forwardTo}`;
-            try {
-              const { status } = await forwardPayload(
-                opts.forwardTo,
-                rawBody,
-                svixHeaders,
-              );
+            if ('error' in forwardResult) {
               process.stderr.write(
-                `${pc.dim('           -> POST')} ${target} ${pc.dim(`[${formatStatus(status)}]`)}\n`,
+                `${pc.dim('           -> POST')} ${target} ${pc.red(`[Error: ${forwardResult.error}]`)}\n`,
               );
-            } catch (err) {
-              const msg = err instanceof Error ? err.message : 'Unknown error';
+            } else {
               process.stderr.write(
-                `${pc.dim('           -> POST')} ${target} ${pc.red(`[Error: ${msg}]`)}\n`,
+                `${pc.dim('           -> POST')} ${target} ${pc.dim(`[${formatStatus(forwardResult.status)}]`)}\n`,
               );
             }
           }
         }
 
-        res.writeHead(200).end('OK');
+        const upstream = resolveUpstream(forwardResult);
+        res.writeHead(upstream.status).end(upstream.body);
       },
     );
 
diff --git a/src/commands/webhooks/resolve-upstream.ts b/src/commands/webhooks/resolve-upstream.ts
new file mode 100644
index 00000000..fdac2ecc
--- /dev/null
+++ b/src/commands/webhooks/resolve-upstream.ts
@@ -0,0 +1,15 @@
+type ForwardResult = { readonly status: number } | { readonly error: string };
+
+export const resolveUpstream = (
+  result: ForwardResult | undefined,
+): { readonly status: number; readonly body: string } => {
+  if (!result) {
+    return { status: 200, body: 'OK' };
+  }
+  if ('error' in result) {
+    return { status: 502, body: 'Forward target unreachable' };
+  }
+  return result.status >= 200 && result.status < 300
+    ? { status: 200, body: 'OK' }
+    : { status: result.status, body: 'Forward target failed' };
+};
diff --git a/tests/commands/webhooks/listen-forward.test.ts b/tests/commands/webhooks/listen-forward.test.ts
new file mode 100644
index 00000000..ffab80ee
--- /dev/null
+++ b/tests/commands/webhooks/listen-forward.test.ts
@@ -0,0 +1,178 @@
+import { createServer, type Server } from 'node:http';
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest';
+import {
+  captureTestEnv,
+  setNonInteractive,
+  setupOutputSpies,
+} from '../../helpers';
+
+const mockCreate = vi.fn(async () => ({
+  data: { object: 'webhook' as const, id: 'wh_test', signing_secret: 'sec' },
+  error: null,
+}));
+const mockRemove = vi.fn(async () => ({ data: null, error: null }));
+
+vi.mock('resend', () => ({
+  Resend: class MockResend {
+    constructor(public key: string) {}
+    webhooks = { create: mockCreate, remove: mockRemove };
+  },
+}));
+
+const postJSON = async (
+  port: number,
+  body: Record<string, unknown>,
+): Promise<{ status: number; body: string }> => {
+  const resp = await fetch(`http://127.0.0.1:${port}`, {
+    method: 'POST',
+    headers: { 'content-type': 'application/json' },
+    body: JSON.stringify(body),
+  });
+  return { status: resp.status, body: await resp.text() };
+};
+
+const startTargetServer = (
+  responseStatus: number,
+): Promise<{ server: Server; port: number }> =>
+  new Promise((resolve) => {
+    const server = createServer((_req, res) => {
+      res.writeHead(responseStatus).end('target response');
+    });
+    server.listen(0, '127.0.0.1', () => {
+      const addr = server.address();
+      const port = typeof addr === 'object' && addr ? addr.port : 0;
+      resolve({ server, port });
+    });
+  });
+
+describe('webhook listen --forward-to status propagation', () => {
+  const restoreEnv = captureTestEnv();
+  let listenerAbort: AbortController | undefined;
+  let targetServer: Server | undefined;
+
+  beforeEach(() => {
+    process.env.RESEND_API_KEY = 're_test_key';
+    mockCreate.mockClear();
+    mockRemove.mockClear();
+  });
+
+  afterEach(() => {
+    restoreEnv();
+    listenerAbort?.abort();
+    listenerAbort = undefined;
+    targetServer?.close();
+    targetServer = undefined;
+    process.removeAllListeners('SIGINT');
+    process.removeAllListeners('SIGTERM');
+  });
+
+  const startListener = async (forwardPort: number): Promise<number> => {
+    setNonInteractive();
+    setupOutputSpies();
+
+    const { listenWebhookCommand } = await import(
+      '../../../src/commands/webhooks/listen'
+    );
+
+    const listenerPort = 10_000 + Math.floor(Math.random() * 50_000);
+
+    listenerAbort = new AbortController();
+
+    listenWebhookCommand
+      .parseAsync(
+        [
+          '--url',
+          'https://tunnel.example.com',
+          '--port',
+          String(listenerPort),
+          '--forward-to',
+          `http://127.0.0.1:${forwardPort}/webhook`,
+        ],
+        { from: 'user' },
+      )
+      .catch(() => {});
+
+    await new Promise((r) => setTimeout(r, 500));
+
+    return listenerPort;
+  };
+
+  it('returns 200 when forward target responds 200', async () => {
+    const target = await startTargetServer(200);
+    targetServer = target.server;
+    const listenerPort = await startListener(target.port);
+
+    const result = await postJSON(listenerPort, {
+      type: 'email.sent',
+      data: { id: 'evt_1' },
+    });
+
+    expect(result.status).toBe(200);
+    expect(result.body).toBe('OK');
+  });
+
+  it('propagates 500 when forward target responds 500', async () => {
+    const target = await startTargetServer(500);
+    targetServer = target.server;
+    const listenerPort = await startListener(target.port);
+
+    const result = await postJSON(listenerPort, {
+      type: 'email.sent',
+      data: { id: 'evt_2' },
+    });
+
+    expect(result.status).toBe(500);
+    expect(result.body).toBe('Forward target failed');
+  });
+
+  it('propagates 401 when forward target responds 401', async () => {
+    const target = await startTargetServer(401);
+    targetServer = target.server;
+    const listenerPort = await startListener(target.port);
+
+    const result = await postJSON(listenerPort, {
+      type: 'email.sent',
+      data: { id: 'evt_3' },
+    });
+
+    expect(result.status).toBe(401);
+    expect(result.body).toBe('Forward target failed');
+  });
+
+  it('returns 502 when forward target is unreachable', async () => {
+    setNonInteractive();
+    setupOutputSpies();
+
+    const { listenWebhookCommand } = await import(
+      '../../../src/commands/webhooks/listen'
+    );
+
+    const listenerPort = 10_000 + Math.floor(Math.random() * 50_000);
+
+    listenerAbort = new AbortController();
+
+    listenWebhookCommand
+      .parseAsync(
+        [
+          '--url',
+          'https://tunnel.example.com',
+          '--port',
+          String(listenerPort),
+          '--forward-to',
+          'http://127.0.0.1:1/unreachable',
+        ],
+        { from: 'user' },
+      )
+      .catch(() => {});
+
+    await new Promise((r) => setTimeout(r, 500));
+
+    const result = await postJSON(listenerPort, {
+      type: 'email.sent',
+      data: { id: 'evt_4' },
+    });
+
+    expect(result.status).toBe(502);
+    expect(result.body).toBe('Forward target unreachable');
+  });
+});
diff --git a/tests/commands/webhooks/resolve-upstream.test.ts b/tests/commands/webhooks/resolve-upstream.test.ts
new file mode 100644
index 00000000..c44e076a
--- /dev/null
+++ b/tests/commands/webhooks/resolve-upstream.test.ts
@@ -0,0 +1,73 @@
+import { describe, expect, it } from 'vitest';
+import { resolveUpstream } from '../../../src/commands/webhooks/resolve-upstream';
+
+describe('resolveUpstream', () => {
+  it('returns 200 OK when no forward result is provided', () => {
+    expect(resolveUpstream(undefined)).toEqual({ status: 200, body: 'OK' });
+  });
+
+  it('returns 200 OK for a 2xx downstream status', () => {
+    expect(resolveUpstream({ status: 200 })).toEqual({
+      status: 200,
+      body: 'OK',
+    });
+    expect(resolveUpstream({ status: 201 })).toEqual({
+      status: 200,
+      body: 'OK',
+    });
+    expect(resolveUpstream({ status: 204 })).toEqual({
+      status: 200,
+      body: 'OK',
+    });
+  });
+
+  it('propagates downstream 4xx status', () => {
+    expect(resolveUpstream({ status: 401 })).toEqual({
+      status: 401,
+      body: 'Forward target failed',
+    });
+    expect(resolveUpstream({ status: 404 })).toEqual({
+      status: 404,
+      body: 'Forward target failed',
+    });
+  });
+
+  it('propagates downstream 5xx status', () => {
+    expect(resolveUpstream({ status: 500 })).toEqual({
+      status: 500,
+      body: 'Forward target failed',
+    });
+    expect(resolveUpstream({ status: 503 })).toEqual({
+      status: 503,
+      body: 'Forward target failed',
+    });
+  });
+
+  it('returns 502 for a forwarding error', () => {
+    expect(resolveUpstream({ error: 'Connection refused' })).toEqual({
+      status: 502,
+      body: 'Forward target unreachable',
+    });
+  });
+
+  it('returns 502 for an unknown forwarding error', () => {
+    expect(resolveUpstream({ error: 'Unknown error' })).toEqual({
+      status: 502,
+      body: 'Forward target unreachable',
+    });
+  });
+
+  it('treats boundary status 300 as failure', () => {
+    expect(resolveUpstream({ status: 300 })).toEqual({
+      status: 300,
+      body: 'Forward target failed',
+    });
+  });
+
+  it('treats boundary status 199 as failure', () => {
+    expect(resolveUpstream({ status: 199 })).toEqual({
+      status: 199,
+      body: 'Forward target failed',
+    });
+  });
+});