diff --git a/src/gateway/test-helpers.e2e.ts b/src/gateway/test-helpers.e2e.ts
index e697e4653db..5815875d526 100644
--- a/src/gateway/test-helpers.e2e.ts
+++ b/src/gateway/test-helpers.e2e.ts
@@ -116,18 +116,123 @@ export async function disconnectGatewayClient(client: GatewayClient): Promise<vo
   await client.stopAndWait();
 }
 
-export async function connectDeviceAuthReq(params: { url: string; token?: string }) {
+const DEVICE_AUTH_REQ_TIMEOUT_MS = 10_000;
+
+async function sleep(ms: number): Promise<void> {
+  await new Promise((resolve) => setTimeout(resolve, ms));
+}
+
+async function waitForWsOpen(ws: WebSocket, timeoutMs: number): Promise<void> {
+  await new Promise<void>((resolve, reject) => {
+    const timer = setTimeout(() => {
+      cleanup();
+      ws.terminate();
+      reject(new Error("timeout waiting for ws open"));
+    }, timeoutMs);
+    const cleanup = () => {
+      clearTimeout(timer);
+      ws.off("open", openHandler);
+      ws.off("error", errorHandler);
+      ws.off("close", closeHandler);
+    };
+    const openHandler = () => {
+      cleanup();
+      resolve();
+    };
+    const errorHandler = (err: Error) => {
+      cleanup();
+      reject(err);
+    };
+    const closeHandler = (code: number, reason: Buffer) => {
+      cleanup();
+      reject(new Error(`closed before open ${code}: ${rawDataToString(reason)}`));
+    };
+    ws.once("open", openHandler);
+    ws.once("error", errorHandler);
+    ws.once("close", closeHandler);
+  });
+}
+
+async function closeWsGracefully(ws: WebSocket, timeoutMs: number): Promise<void> {
+  if (ws.readyState === WebSocket.CLOSED) {
+    return;
+  }
+  await new Promise<void>((resolve) => {
+    const timer = setTimeout(() => {
+      cleanup();
+      ws.terminate();
+      resolve();
+    }, timeoutMs);
+    const cleanup = () => {
+      clearTimeout(timer);
+      ws.off("close", closeHandler);
+      ws.off("error", errorHandler);
+    };
+    const closeHandler = () => {
+      cleanup();
+      resolve();
+    };
+    const errorHandler = () => {
+      cleanup();
+      resolve();
+    };
+    ws.once("close", closeHandler);
+    ws.once("error", errorHandler);
+    if (ws.readyState === WebSocket.OPEN) {
+      ws.close();
+    } else if (ws.readyState !== WebSocket.CLOSING) {
+      ws.terminate();
+    }
+  });
+}
+
+export async function connectDeviceAuthReq(params: {
+  url: string;
+  token?: string;
+  timeoutMs?: number;
+}) {
+  const timeoutMs = params.timeoutMs ?? DEVICE_AUTH_REQ_TIMEOUT_MS;
+  const deadline = Date.now() + timeoutMs;
+  let lastError: Error | undefined;
+  while (Date.now() < deadline) {
+    const attemptTimeoutMs = Math.max(250, Math.min(5000, deadline - Date.now()));
+    try {
+      return await connectDeviceAuthReqOnce({ ...params, timeoutMs: attemptTimeoutMs });
+    } catch (err) {
+      lastError = err instanceof Error ? err : new Error(String(err));
+      await sleep(Math.min(100, Math.max(0, deadline - Date.now())));
+    }
+  }
+  throw new Error(
+    `device auth request failed after ${timeoutMs}ms: ${lastError?.message ?? "unknown error"}`,
+  );
+}
+
+async function connectDeviceAuthReqOnce(params: {
+  url: string;
+  token?: string;
+  timeoutMs: number;
+}) {
   const ws = new WebSocket(params.url);
   const connectNoncePromise = new Promise<string>((resolve, reject) => {
-    const timer = setTimeout(
-      () => reject(new Error("timeout waiting for connect challenge")),
-      5000,
-    );
-    const closeHandler = (code: number, reason: Buffer) => {
+    const timer = setTimeout(() => {
+      cleanup();
+      reject(new Error("timeout waiting for connect challenge"));
+    }, params.timeoutMs);
+    const cleanup = () => {
       clearTimeout(timer);
       ws.off("message", handler);
+      ws.off("close", closeHandler);
+      ws.off("error", errorHandler);
+    };
+    const closeHandler = (code: number, reason: Buffer) => {
+      cleanup();
       reject(new Error(`closed ${code}: ${rawDataToString(reason)}`));
     };
+    const errorHandler = (err: Error) => {
+      cleanup();
+      reject(err);
+    };
     const handler = (data: WebSocket.RawData) => {
       try {
         const obj = JSON.parse(rawDataToString(data)) as {
@@ -142,9 +247,7 @@ export async function connectDeviceAuthReq(params: { url: string; token?: string
         if (typeof nonce !== "string" || nonce.trim().length === 0) {
           return;
         }
-        clearTimeout(timer);
-        ws.off("message", handler);
-        ws.off("close", closeHandler);
+        cleanup();
         resolve(nonce.trim());
       } catch {
         // ignore parse errors while waiting for challenge
@@ -152,9 +255,18 @@ export async function connectDeviceAuthReq(params: { url: string; token?: string
     };
     ws.on("message", handler);
     ws.once("close", closeHandler);
+    ws.once("error", errorHandler);
+  });
+  try {
+    await waitForWsOpen(ws, params.timeoutMs);
+  } catch (err) {
+    ws.terminate();
+    throw err;
+  }
+  const connectNonce = await connectNoncePromise.catch((err: unknown) => {
+    ws.terminate();
+    throw err;
   });
-  await new Promise<void>((resolve) => ws.once("open", resolve));
-  const connectNonce = await connectNoncePromise;
   const identity = loadOrCreateDeviceIdentity();
   const signedAtMs = Date.now();
   const platform = process.platform;
@@ -176,6 +288,49 @@ export async function connectDeviceAuthReq(params: { url: string; token?: string
     signedAt: signedAtMs,
     nonce: connectNonce,
   };
+  const responsePromise = new Promise<{
+    type: "res";
+    id: string;
+    ok: boolean;
+    error?: { message?: string };
+  }>((resolve, reject) => {
+    const timer = setTimeout(() => {
+      cleanup();
+      reject(new Error("timeout waiting for connect response"));
+    }, params.timeoutMs);
+    const cleanup = () => {
+      clearTimeout(timer);
+      ws.off("message", handler);
+      ws.off("close", closeHandler);
+      ws.off("error", errorHandler);
+    };
+    const closeHandler = (code: number, reason: Buffer) => {
+      cleanup();
+      reject(new Error(`closed ${code}: ${rawDataToString(reason)}`));
+    };
+    const errorHandler = (err: Error) => {
+      cleanup();
+      reject(err);
+    };
+    const handler = (data: WebSocket.RawData) => {
+      const obj = JSON.parse(rawDataToString(data)) as { type?: unknown; id?: unknown };
+      if (obj?.type !== "res" || obj?.id !== "c1") {
+        return;
+      }
+      cleanup();
+      resolve(
+        obj as {
+          type: "res";
+          id: string;
+          ok: boolean;
+          error?: { message?: string };
+        },
+      );
+    };
+    ws.on("message", handler);
+    ws.once("close", closeHandler);
+    ws.once("error", errorHandler);
+  });
   ws.send(
     JSON.stringify({
       type: "req",
@@ -197,39 +352,11 @@ export async function connectDeviceAuthReq(params: { url: string; token?: string
       },
     }),
   );
-  const res = await new Promise<{
-    type: "res";
-    id: string;
-    ok: boolean;
-    error?: { message?: string };
-  }>((resolve, reject) => {
-    const timer = setTimeout(() => reject(new Error("timeout")), 5000);
-    const closeHandler = (code: number, reason: Buffer) => {
-      clearTimeout(timer);
-      ws.off("message", handler);
-      reject(new Error(`closed ${code}: ${rawDataToString(reason)}`));
-    };
-    const handler = (data: WebSocket.RawData) => {
-      const obj = JSON.parse(rawDataToString(data)) as { type?: unknown; id?: unknown };
-      if (obj?.type !== "res" || obj?.id !== "c1") {
-        return;
-      }
-      clearTimeout(timer);
-      ws.off("message", handler);
-      ws.off("close", closeHandler);
-      resolve(
-        obj as {
-          type: "res";
-          id: string;
-          ok: boolean;
-          error?: { message?: string };
-        },
-      );
-    };
-    ws.on("message", handler);
-    ws.once("close", closeHandler);
+  const res = await responsePromise.catch((err: unknown) => {
+    ws.terminate();
+    throw err;
   });
-  ws.close();
+  await closeWsGracefully(ws, Math.min(1000, params.timeoutMs));
   return res;
 }