diff --git a/.changeset/verify-preview-tunnels.md b/.changeset/verify-preview-tunnels.md
new file mode 100644
index 000000000..c76f46554
--- /dev/null
+++ b/.changeset/verify-preview-tunnels.md
@@ -0,0 +1,5 @@
+---
+'@tanstack/ai-sandbox-cloudflare': patch
+---
+
+`exposePreview` now verifies the preview URL is actually reachable before returning it: it fails with an actionable error when nothing is listening on the port, and detects and replaces stale quick tunnels instead of re-sharing dead URLs (#992).
diff --git a/packages/ai-sandbox-cloudflare/src/preview-tool.ts b/packages/ai-sandbox-cloudflare/src/preview-tool.ts
index 359049b75..9096ee2a9 100644
--- a/packages/ai-sandbox-cloudflare/src/preview-tool.ts
+++ b/packages/ai-sandbox-cloudflare/src/preview-tool.ts
@@ -68,6 +68,87 @@ export const PREVIEW_GUIDANCE: string = [
   'Once it is listening, call `exposePreview` with that port, then share the URL.',
 ].join('\n')
 
+const LOCAL_PROBE_TIMEOUT_MS = 5_000
+// Fresh quick tunnels need a few seconds of DNS/edge propagation, hence retries.
+const EDGE_PROBE_ATTEMPTS = 5
+const EDGE_PROBE_BASE_DELAY_MS = 250
+const EDGE_PROBE_FETCH_TIMEOUT_MS = 3_000
+
+/**
+ * Probe the port INSIDE the sandbox via `containerFetch`. Returns the HTTP
+ * status when a listener answered (any response — 4xx/5xx included — proves one
+ * exists), or the failure symptom (a string) when nothing did.
+ */
+async function localProbe(
+  sandbox: Sandbox,
+  port: number,
+): Promise<number | string> {
+  // A race instead of AbortSignal: signals don't serialize across the sandbox
+  // RPC boundary, and a lost in-flight probe response is harmless.
+  let timeoutId: ReturnType<typeof setTimeout> | undefined
+  const timeout = new Promise<never>((_, reject) => {
+    timeoutId = setTimeout(
+      () => reject(new Error(`no response within ${LOCAL_PROBE_TIMEOUT_MS}ms`)),
+      LOCAL_PROBE_TIMEOUT_MS,
+    )
+  })
+  try {
+    const res = await Promise.race([
+      sandbox.containerFetch('http://preview/', { method: 'HEAD' }, port),
+      timeout,
+    ])
+    return res.status
+  } catch (error) {
+    return error instanceof Error ? error.message : String(error)
+  } finally {
+    clearTimeout(timeoutId)
+  }
+}
+
+/**
+ * Probe a tunnel URL through the public edge with bounded retries. Only 502/530
+ * — Cloudflare's tunnel/origin-unreachable signatures — mark the URL as
+ * unreachable (401/403/404 prove the server answered, and `redirect: 'manual'`
+ * keeps a login redirect from probing some other site), and even those are
+ * trusted when the app answered the SAME status locally, so an app's own
+ * 502/530 never gets its healthy tunnel destroyed. The verdict split exists
+ * because only an OBSERVED non-matching 502/530 ('stale') is evidence that
+ * justifies destroying the tunnel; fetch exceptions ('unverified') prove
+ * nothing about it — the probe path itself may be what failed.
+ */
+async function edgeProbeFailure(
+  url: string,
+  localStatus: number,
+): Promise<{ verdict: 'stale' | 'unverified'; symptom: string } | null> {
+  let lastFailure = 'no response'
+  let verdict: 'stale' | 'unverified' = 'unverified'
+  for (let attempt = 0; attempt < EDGE_PROBE_ATTEMPTS; attempt += 1) {
+    if (attempt > 0) {
+      await new Promise((resolve) =>
+        setTimeout(resolve, EDGE_PROBE_BASE_DELAY_MS * 2 ** (attempt - 1)),
+      )
+    }
+    try {
+      const res = await fetch(url, {
+        method: 'HEAD',
+        redirect: 'manual',
+        signal: AbortSignal.timeout(EDGE_PROBE_FETCH_TIMEOUT_MS),
+      })
+      if (
+        (res.status !== 502 && res.status !== 530) ||
+        res.status === localStatus
+      ) {
+        return null
+      }
+      lastFailure = `HTTP ${res.status}`
+      verdict = 'stale'
+    } catch (error) {
+      lastFailure = error instanceof Error ? error.message : String(error)
+    }
+  }
+  return { verdict, symptom: lastFailure }
+}
+
 /**
  * Build the `exposePreview` server tool for one run. Starting a tunnel is a
  * HOST-side call on the Sandbox DO stub, so an in-sandbox agent cannot make it from
@@ -100,11 +181,51 @@ export function exposePreviewTool(input: StartRunInput, env: PreviewToolEnv) {
     const sandbox = getSandbox(env.Sandbox, input.threadId, {
       transport: 'rpc',
     })
+    // Gate tunnel work on a live listener: a fresh tunnel to a dead port is still
+    // a dead preview, and the failure the agent can FIX is "start the server".
+    const local = await localProbe(sandbox, port)
+    if (typeof local === 'string') {
+      throw new Error(
+        `No server is listening on port ${port} inside the sandbox (${local}). Start the dev server (bound to 0.0.0.0:${port}) first, then retry exposePreview.`,
+      )
+    }
     // A Cloudflare quick tunnel (`*.trycloudflare.com`) run by `cloudflared` INSIDE
     // the sandbox: it bypasses the local Vite dev server's port entirely (so Vite
     // can't hijack the preview's asset requests) and needs no custom domain on a
     // deploy. `get(port)` is idempotent per port. See the Sandbox SDK `tunnels` API.
     const tunnel = await sandbox.tunnels.get(port)
-    return { url: tunnel.url }
+    const edgeFailure = await edgeProbeFailure(tunnel.url, local)
+    if (edgeFailure === null) return { url: tunnel.url }
+    // Never destroy on 'unverified': the tunnel may be healthy with only the
+    // probe path broken, so destroying it could kill a working preview.
+    if (edgeFailure.verdict === 'unverified') {
+      throw new Error(
+        `Port ${port} is serving inside the sandbox, but the preview tunnel could not be verified from the edge (${edgeFailure.symptom}). The tunnel was left in place — retry exposePreview in a few seconds.`,
+      )
+    }
+    // Local server healthy but the edge kept answering 502/530: the cached tunnel
+    // record is suspect. Refresh, bounded to ONE so we never churn tunnels.
+    await sandbox.tunnels.destroy(port)
+    const fresh = await sandbox.tunnels.get(port)
+    const freshFailure = await edgeProbeFailure(fresh.url, local)
+    if (freshFailure === null) {
+      return {
+        url: fresh.url,
+        note: `The tunnel for port ${port} was stale, so it was replaced. Any previously shared preview URL for this port is dead — share this new URL instead.`,
+      }
+    }
+    const [diagnosis, hint] =
+      freshFailure.verdict === 'stale'
+        ? [
+            'its preview tunnel never became reachable',
+            'Retry exposePreview, and if it keeps failing, restart the dev server and try again.',
+          ]
+        : [
+            'the replacement preview tunnel could not be verified from the edge',
+            'Retry exposePreview in a few seconds.',
+          ]
+    throw new Error(
+      `Port ${port} is serving inside the sandbox, but ${diagnosis} (old tunnel: ${edgeFailure.symptom}; replacement tunnel: ${freshFailure.symptom}). ${hint}`,
+    )
   })
 }
diff --git a/packages/ai-sandbox-cloudflare/tests/preview-tool.test.ts b/packages/ai-sandbox-cloudflare/tests/preview-tool.test.ts
index 64fd9e261..f64990985 100644
--- a/packages/ai-sandbox-cloudflare/tests/preview-tool.test.ts
+++ b/packages/ai-sandbox-cloudflare/tests/preview-tool.test.ts
@@ -1,11 +1,12 @@
 /**
  * Deterministic tests for the browser-preview building blocks (no Workers
- * runtime). `getSandbox` is module-mocked to a stub whose `tunnels.get` records
- * its calls, so we can assert the tool opens a quick tunnel to the right port and
- * returns its URL, and that `PREVIEW_GUIDANCE` carries the directives an agent
- * needs (allow-all-hosts, non-3000 port, call exposePreview).
+ * runtime). `getSandbox` is module-mocked to a stub recording `containerFetch`
+ * (the in-container listener probe) and `tunnels.get`/`tunnels.destroy`, and the
+ * global `fetch` (the public edge probe) is stubbed, so the tool's
+ * verify-then-return contract is assertable without a sandbox. `PREVIEW_GUIDANCE`
+ * is asserted to carry the directives an agent needs.
  */
-import { describe, expect, it, vi } from 'vitest'
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
 import type { Sandbox } from '@cloudflare/sandbox'
 import type { StartRunInput } from '../src/coordinator'
 
@@ -14,33 +15,67 @@ import type { StartRunInput } from '../src/coordinator'
 // lib's) — use it bare, the way the package's own modules do.
 
 // Hoisted so the `vi.mock` factory can close over the same spies the tests assert on.
-const { tunnelGetMock, getSandboxMock } = vi.hoisted(() => {
-  const tunnelGetMock = vi.fn<(port: number) => Promise<{ url: string }>>()
-  return {
-    tunnelGetMock,
-    getSandboxMock: vi.fn(() => ({ tunnels: { get: tunnelGetMock } })),
-  }
-})
+const { containerFetchMock, tunnelGetMock, tunnelDestroyMock, getSandboxMock } =
+  vi.hoisted(() => {
+    const containerFetchMock =
+      vi.fn<
+        (url: string, init: RequestInit, port: number) => Promise<Response>
+      >()
+    const tunnelGetMock = vi.fn<(port: number) => Promise<{ url: string }>>()
+    const tunnelDestroyMock = vi.fn<(port: number) => Promise<void>>()
+    return {
+      containerFetchMock,
+      tunnelGetMock,
+      tunnelDestroyMock,
+      getSandboxMock: vi.fn(() => ({
+        containerFetch: containerFetchMock,
+        tunnels: { get: tunnelGetMock, destroy: tunnelDestroyMock },
+      })),
+    }
+  })
 vi.mock('@cloudflare/sandbox', () => ({ getSandbox: getSandboxMock }))
 
+// The edge probe goes through the global `fetch` (a plain Worker subrequest).
+const edgeFetchMock =
+  vi.fn<(url: string, init?: RequestInit) => Promise<Response>>()
+vi.stubGlobal('fetch', edgeFetchMock)
+
 // Imported AFTER the mock is registered.
 const { PREVIEW_GUIDANCE, exposePreviewTool } =
   await import('../src/preview-tool')
 
 const SANDBOX = {} as unknown as DurableObjectNamespace<Sandbox>
+const OLD_URL = 'https://two-words-here.trycloudflare.com'
+const NEW_URL = 'https://fresh-words-here.trycloudflare.com'
+
+const http = (status: number) => new Response(null, { status })
 
-function runInput(overrides: Partial<StartRunInput> = {}): StartRunInput {
-  return { runId: 'r1', threadId: 'thread-x', messages: [], ...overrides }
+function makeTool() {
+  const input: StartRunInput = {
+    runId: 'r1',
+    threadId: 'thread-x',
+    messages: [],
+  }
+  return exposePreviewTool(input, { Sandbox: SANDBOX })
 }
 
-describe('exposePreviewTool', () => {
-  it('opens a quick tunnel on the run’s container for the given port', async () => {
-    tunnelGetMock.mockResolvedValue({
-      url: 'https://two-words-here.trycloudflare.com',
-    })
-    const tool = exposePreviewTool(runInput(), { Sandbox: SANDBOX })
+beforeEach(() => {
+  getSandboxMock.mockClear()
+  // mockReset, not mockClear: leftover `mockResolvedValueOnce` queues from one
+  // test would leak into the next.
+  containerFetchMock.mockReset().mockResolvedValue(http(200))
+  tunnelGetMock.mockReset().mockResolvedValue({ url: OLD_URL })
+  tunnelDestroyMock.mockReset().mockResolvedValue(undefined)
+  edgeFetchMock.mockReset().mockResolvedValue(http(200))
+})
 
-    const result = await tool.execute?.({ port: 5173 })
+afterEach(() => {
+  vi.useRealTimers()
+})
+
+describe('exposePreviewTool', () => {
+  it('opens a quick tunnel on the run’s container and returns its URL once verified', async () => {
+    const result = await makeTool().execute?.({ port: 5173 })
 
     // The run's container is addressed by threadId, over the RPC transport that
     // `sandbox.tunnels` requires; the tunnel targets the dev port.
@@ -48,7 +83,93 @@ describe('exposePreviewTool', () => {
       transport: 'rpc',
     })
     expect(tunnelGetMock).toHaveBeenCalledWith(5173)
-    expect(result).toEqual({ url: 'https://two-words-here.trycloudflare.com' })
+    expect(result).toEqual({ url: OLD_URL })
+  })
+
+  it('fails with an actionable error — and mints no tunnel — when nothing listens on the port', async () => {
+    vi.useFakeTimers()
+    // A probe that never settles: the tool's own timeout must bound it.
+    containerFetchMock.mockReturnValue(new Promise<Response>(() => {}))
+
+    const promise = makeTool().execute?.({ port: 5173 })
+    const assertion = expect(promise).rejects.toThrow(/listening on port 5173/)
+    await vi.runAllTimersAsync()
+    await assertion
+
+    expect(tunnelGetMock).not.toHaveBeenCalled()
+  })
+
+  it('counts local 5xx as a live listener and edge 4xx / transient failures as reachable', async () => {
+    vi.useFakeTimers()
+    // An auth-protected app: 500 locally, and the edge needs one propagation
+    // retry before answering 403. None of that means the tunnel is stale.
+    containerFetchMock.mockResolvedValue(http(500))
+    edgeFetchMock
+      .mockRejectedValueOnce(new Error('DNS not propagated'))
+      .mockResolvedValue(http(403))
+
+    const promise = makeTool().execute?.({ port: 5173 })
+    await vi.runAllTimersAsync()
+
+    await expect(promise).resolves.toEqual({ url: OLD_URL })
+    expect(tunnelDestroyMock).not.toHaveBeenCalled()
+  })
+
+  it('does not replace the tunnel when the app itself answers 502 (same status locally and at the edge)', async () => {
+    containerFetchMock.mockResolvedValue(http(502))
+    edgeFetchMock.mockResolvedValue(http(502))
+
+    const result = await makeTool().execute?.({ port: 5173 })
+
+    expect(result).toEqual({ url: OLD_URL })
+    expect(tunnelDestroyMock).not.toHaveBeenCalled()
+  })
+
+  it('leaves the tunnel alone when the edge probe only ever throws (unverified, not stale)', async () => {
+    vi.useFakeTimers()
+    // Timeouts/DNS failures say nothing about the tunnel — it must survive.
+    edgeFetchMock.mockRejectedValue(new Error('subrequest failed'))
+
+    const promise = makeTool().execute?.({ port: 5173 })
+    const assertion = expect(promise).rejects.toThrow(/could not be verified/)
+    await vi.runAllTimersAsync()
+    await assertion
+
+    expect(tunnelDestroyMock).not.toHaveBeenCalled()
+  })
+
+  it('replaces a stale tunnel (local healthy, edge stuck on 502) and flags the old URL as dead', async () => {
+    vi.useFakeTimers()
+    tunnelGetMock
+      .mockResolvedValueOnce({ url: OLD_URL })
+      .mockResolvedValueOnce({ url: NEW_URL })
+    // The stale tunnel 502s no matter how often it's probed; the fresh one works.
+    edgeFetchMock.mockImplementation((url) =>
+      Promise.resolve(http(url === NEW_URL ? 200 : 502)),
+    )
+
+    const promise = makeTool().execute?.({ port: 5173 })
+    await vi.runAllTimersAsync()
+
+    await expect(promise).resolves.toMatchObject({
+      url: NEW_URL,
+      note: expect.stringMatching(/dead/),
+    })
+    expect(tunnelDestroyMock).toHaveBeenCalledWith(5173)
+  })
+
+  it('errors instead of returning a URL when the replacement tunnel never becomes reachable', async () => {
+    vi.useFakeTimers()
+    edgeFetchMock.mockResolvedValue(http(502))
+
+    const promise = makeTool().execute?.({ port: 5173 })
+    // Attach the rejection handler BEFORE running the timers, or the rejection
+    // fires unhandled while the fake clock advances.
+    const assertion = expect(promise).rejects.toThrow(
+      /Port 5173 is serving inside the sandbox/,
+    )
+    await vi.runAllTimersAsync()
+    await assertion
   })
 })
 
diff --git a/scripts/lovable-gateway.models.json b/scripts/lovable-gateway.models.json
index 8a193376e..79c6babbc 100644
--- a/scripts/lovable-gateway.models.json
+++ b/scripts/lovable-gateway.models.json
@@ -12,15 +12,8 @@
     "max_tokens": 65536,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "audio",
-        "video"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text", "image", "audio", "video"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -85,15 +78,8 @@
     "max_tokens": 65536,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "video"
-      ],
-      "output": [
-        "text",
-        "image"
-      ]
+      "input": ["text", "image", "video"],
+      "output": ["text", "image"]
     },
     "pricing": {
       "input": {
@@ -150,15 +136,8 @@
     "max_tokens": 65536,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "audio",
-        "video"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text", "image", "audio", "video"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -222,12 +201,8 @@
     "context_window": 8192,
     "max_tokens": 16384,
     "modalities": {
-      "input": [
-        "text"
-      ],
-      "output": [
-        "audio"
-      ]
+      "input": ["text"],
+      "output": ["audio"]
     },
     "pricing": {
       "input": {
@@ -265,12 +240,8 @@
     "max_tokens": 16384,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text"
-      ],
-      "output": [
-        "audio"
-      ]
+      "input": ["text"],
+      "output": ["audio"]
     },
     "pricing": {
       "input": {
@@ -308,15 +279,8 @@
     "max_tokens": 65536,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "audio",
-        "video"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text", "image", "audio", "video"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -406,12 +370,8 @@
     "max_tokens": 16384,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text"
-      ],
-      "output": [
-        "audio"
-      ]
+      "input": ["text"],
+      "output": ["audio"]
     },
     "pricing": {
       "input": {
@@ -449,15 +409,8 @@
     "max_tokens": 65000,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "audio",
-        "video"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text", "image", "audio", "video"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -522,15 +475,8 @@
     "max_tokens": 32768,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "video"
-      ],
-      "output": [
-        "text",
-        "image"
-      ]
+      "input": ["text", "image", "video"],
+      "output": ["text", "image"]
     },
     "pricing": {
       "input": {
@@ -595,15 +541,8 @@
     "max_tokens": 32768,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "video"
-      ],
-      "output": [
-        "text",
-        "image"
-      ]
+      "input": ["text", "image", "video"],
+      "output": ["text", "image"]
     },
     "pricing": {
       "input": {
@@ -668,15 +607,8 @@
     "max_tokens": 65000,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "audio",
-        "video"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text", "image", "audio", "video"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -740,15 +672,8 @@
     "context_window": 65536,
     "max_tokens": 4096,
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "video"
-      ],
-      "output": [
-        "text",
-        "image"
-      ]
+      "input": ["text", "image", "video"],
+      "output": ["text", "image"]
     },
     "pricing": {
       "input": {
@@ -813,12 +738,8 @@
     "max_tokens": 16384,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text"
-      ],
-      "output": [
-        "audio"
-      ]
+      "input": ["text"],
+      "output": ["audio"]
     },
     "pricing": {
       "input": {
@@ -856,15 +777,8 @@
     "max_tokens": 64000,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "audio",
-        "video"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text", "image", "audio", "video"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -954,15 +868,8 @@
     "max_tokens": 64000,
     "knowledge": "2025-01",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "audio",
-        "video"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text", "image", "audio", "video"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -1027,15 +934,8 @@
     "max_tokens": 64000,
     "knowledge": "2026-03",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "audio",
-        "video"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text", "image", "audio", "video"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -1100,12 +1000,8 @@
     "max_tokens": 0,
     "knowledge": "2025-05",
     "modalities": {
-      "input": [
-        "text"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -1133,15 +1029,8 @@
     "max_tokens": 0,
     "knowledge": "2025-11",
     "modalities": {
-      "input": [
-        "text",
-        "image",
-        "audio",
-        "video"
-      ],
-      "output": [
-        "text"
-      ]
+      "input": ["text", "image", "audio", "video"],
+      "output": ["text"]
     },
     "pricing": {
       "input": {
@@ -1192,13 +1081,8 @@
     "context_window": 0,
     "max_tokens": 0,
     "modalities": {
-      "input": [
-        "text",
-        "image"
-      ],
-      "output": [
-        "video"
-      ]
+      "input": ["text", "image"],
+      "output": ["video"]
     },
     "pricing": {
       "video_duration": {
@@ -1226,13 +1110,8 @@
     "context_window": 0,
     "max_tokens": 0,
     "modalities": {
-      "input": [
-        "text",
-        "image"
-      ],
-      "output": [
-        "video"
-      ]
+      "input": ["text", "image"],
+      "output": ["video"]
     },
     "pricing": {
       "video_duration": {
@@ -1260,13 +1139,8 @@
     "context_window": 0,
     "max_tokens": 0,
     "modalities": {
-      "input": [
-        "text",
-        "image"
-      ],
-      "output": [
-        "video"
-      ]
+      "input": ["text", "image"],
+      "output": ["video"]
     },
     "pricing": {
       "video_duration": {
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