diff --git a/CHANGELOG.md b/CHANGELOG.md
index 15ac01e6c4..53234070e3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -116,13 +116,21 @@ file is the human-readable summary of what changed and why.
   costing no space until the guest writes something. On macOS the clone never
   happened: the copy fell back to writing the whole 8 GB image out byte for
   byte, filling in the empty space the image leaves sparse. Creating or
-  resetting a sandbox spent that time writing gigabytes, then the guest booted
-  while the disk was still catching up and had to compete for it — which is why
-  a sandbox's first start could crawl and sometimes gave up with "sandbox
-  server did not become healthy" before finishing. The clone now happens for
-  real: creation is immediate, a sandbox costs roughly nothing on disk until it
-  is used, and first start takes about as long as every start after it.
+  resetting a sandbox spent that time writing gigabytes to disk. The clone now
+  happens for real: creation is immediate, and a sandbox costs roughly nothing
+  on disk until it is used.
   ([#293](https://github.com/quickbeard/codev-code/pull/293))
+- **Starting a sandbox no longer hangs for minutes** — a sandbox would
+  sometimes sit on "starting" for five minutes and then give up with "sandbox
+  server did not become healthy", even though the guest inside it had finished
+  booting seconds in. While waiting for the guest, the app checks its health
+  over and over, one check at a time. Those checks had no deadline, so when one
+  connected to a guest that was still opening its port and then got no answer
+  at all, that single check waited forever and every check behind it queued up
+  behind it — the sandbox was ready, and nothing was left to notice. Each check
+  now gives up after two seconds and the next one carries on, so a stalled
+  connection costs a moment instead of the whole startup.
+  ([#294](https://github.com/quickbeard/codev-code/pull/294))
 - **Work sessions reach the model on WSL's mirrored networking** — on Windows,
   a sandbox's model traffic crosses from the WSL guest to a relay on the
   Windows host, and the guest found the host by assuming WSL's default NAT
diff --git a/packages/codev-sandbox/src/boot.test.ts b/packages/codev-sandbox/src/boot.test.ts
index e769f364b1..f0f918426c 100644
--- a/packages/codev-sandbox/src/boot.test.ts
+++ b/packages/codev-sandbox/src/boot.test.ts
@@ -1,5 +1,5 @@
 import { expect, test } from "bun:test"
-import { generateSandboxCredentials, pollSandboxHealth, sandboxBootEnv } from "./boot"
+import { checkSandboxHealth, generateSandboxCredentials, pollSandboxHealth, sandboxBootEnv } from "./boot"
 
 test("boot env mirrors the WSL sidecar contract and carries the server address", () => {
   expect(
@@ -62,3 +62,42 @@ test("health polling returns once the server responds", async () => {
   )
   expect(checks).toBe(3)
 })
+
+// pollSandboxHealth awaits each probe in turn, so a request that never answers
+// used to stall the whole loop: the sandbox stayed "starting" until the start
+// timeout gave up, minutes later, even though the guest had come up seconds in.
+// A probe must always settle.
+test("health probe gives up on a connection that never answers", async () => {
+  const started = Date.now()
+  const healthy = await checkSandboxHealth(
+    "http://127.0.0.1:1",
+    { username: "codev", password: "secret" },
+    // Opens and then hangs, the way an accepted socket to a guest that is not
+    // listening yet can: no response, no error.
+    ((_url: string, init?: RequestInit) =>
+      new Promise((_resolve, reject) => {
+        init?.signal?.addEventListener("abort", () => reject(new Error("aborted")))
+      })) as unknown as typeof fetch,
+  )
+
+  expect(healthy).toBe(false)
+  expect(Date.now() - started).toBeLessThan(10_000)
+})
+
+// The caller's signal must cancel an in-flight probe too, so aborting the poll
+// does not leave a request outliving the start it belonged to.
+test("health probe aborts with the caller's signal", async () => {
+  const controller = new AbortController()
+  const probe = checkSandboxHealth(
+    "http://127.0.0.1:1",
+    { username: "codev", password: "secret" },
+    ((_url: string, init?: RequestInit) =>
+      new Promise((_resolve, reject) => {
+        init?.signal?.addEventListener("abort", () => reject(new Error("aborted")))
+      })) as unknown as typeof fetch,
+    controller.signal,
+  )
+  controller.abort()
+
+  expect(await probe).toBe(false)
+})
diff --git a/packages/codev-sandbox/src/boot.ts b/packages/codev-sandbox/src/boot.ts
index 2055bb2ef7..de82453835 100644
--- a/packages/codev-sandbox/src/boot.ts
+++ b/packages/codev-sandbox/src/boot.ts
@@ -56,13 +56,27 @@ export function sandboxBootEnv(
 // Absolute guest path of the launcher baked into every image.
 export const SANDBOX_GUEST_LAUNCHER = "/opt/codev-guest/server-launch.mjs"
 
+// A probe must not be able to outlive its usefulness. pollSandboxHealth awaits
+// each attempt in turn, so one request that opens and then never answers stalls
+// every later attempt forever — the sandbox never comes up, and the start
+// timeout is the only thing left to end it. That happens in practice: the
+// forwarder accepts the TCP connection and dials through to the guest while its
+// server is still binding the port, and the connection can be left hanging
+// rather than refused. A healthy guest answers in single-digit milliseconds, so
+// a short deadline costs a live probe nothing and turns a permanent hang into
+// one skipped attempt.
+const HEALTH_REQUEST_TIMEOUT_MS = 2_000
+
 export async function checkSandboxHealth(
   url: string,
   credentials: SandboxCredentials,
   fetchImpl: typeof fetch = fetch,
+  signal?: AbortSignal,
 ) {
+  const deadline = AbortSignal.timeout(HEALTH_REQUEST_TIMEOUT_MS)
   const response = await fetchImpl(`${url}/global/health`, {
     headers: { authorization: `Basic ${btoa(`${credentials.username}:${credentials.password}`)}` },
+    signal: signal ? AbortSignal.any([signal, deadline]) : deadline,
   }).catch(() => null)
   return !!response?.ok
 }
diff --git a/packages/codev-sandbox/src/bwrap/provider.ts b/packages/codev-sandbox/src/bwrap/provider.ts
index 676e15b31d..e5f64b97fe 100644
--- a/packages/codev-sandbox/src/bwrap/provider.ts
+++ b/packages/codev-sandbox/src/bwrap/provider.ts
@@ -185,7 +185,7 @@ export function createBwrapProvider(options: BwrapProviderOptions): SandboxProvi
       const abort = new AbortController()
       let timeoutHandle: ReturnType<typeof setTimeout> | undefined
       const outcome = await Promise.race([
-        pollSandboxHealth(() => checkSandboxHealth(url, credentials, fetchImpl), abort.signal).then(
+        pollSandboxHealth(() => checkSandboxHealth(url, credentials, fetchImpl, abort.signal), abort.signal).then(
           () => "healthy" as const,
         ),
         exited,
diff --git a/packages/codev-sandbox/src/vz/provider.ts b/packages/codev-sandbox/src/vz/provider.ts
index 4a2288010b..e3cd349819 100644
--- a/packages/codev-sandbox/src/vz/provider.ts
+++ b/packages/codev-sandbox/src/vz/provider.ts
@@ -249,7 +249,7 @@ export function createVzProvider(options: VzProviderOptions): SandboxProvider {
       const url = `http://127.0.0.1:${forwarder.port}`
       const abort = new AbortController()
       const healthOutcome = await Promise.race([
-        pollSandboxHealth(() => checkSandboxHealth(url, credentials, fetchImpl), abort.signal).then(
+        pollSandboxHealth(() => checkSandboxHealth(url, credentials, fetchImpl, abort.signal), abort.signal).then(
           () => "healthy" as const,
         ),
         helperError,
diff --git a/packages/codev-sandbox/src/wsl/provider.ts b/packages/codev-sandbox/src/wsl/provider.ts
index 2019d71ce5..f25fb2b678 100644
--- a/packages/codev-sandbox/src/wsl/provider.ts
+++ b/packages/codev-sandbox/src/wsl/provider.ts
@@ -386,7 +386,7 @@ export function createWslProvider(options: WslProviderOptions): SandboxProvider
       const abort = new AbortController()
       let timeoutHandle: ReturnType<typeof setTimeout> | undefined
       const outcome = await Promise.race([
-        pollSandboxHealth(() => checkSandboxHealth(url, credentials, fetchImpl), abort.signal).then(
+        pollSandboxHealth(() => checkSandboxHealth(url, credentials, fetchImpl, abort.signal), abort.signal).then(
           () => "healthy" as const,
         ),
         exited,