diff --git a/src/gateway/gateway-acp-bind.live.test.ts b/src/gateway/gateway-acp-bind.live.test.ts
index e9ff122933d..c1864fdb4dd 100644
--- a/src/gateway/gateway-acp-bind.live.test.ts
+++ b/src/gateway/gateway-acp-bind.live.test.ts
@@ -99,9 +99,40 @@ async function waitForGatewayPort(params: {
 }
 
 async function connectClient(params: { url: string; token: string; timeoutMs?: number }) {
+  const timeoutMs = params.timeoutMs ?? CONNECT_TIMEOUT_MS;
+  const startedAt = Date.now();
+  let attempt = 0;
+  let lastError: Error | null = null;
+
+  while (Date.now() - startedAt < timeoutMs) {
+    attempt += 1;
+    const remainingMs = timeoutMs - (Date.now() - startedAt);
+    if (remainingMs <= 0) {
+      break;
+    }
+    try {
+      return await connectClientOnce({
+        ...params,
+        timeoutMs: Math.min(remainingMs, 35_000),
+      });
+    } catch (error) {
+      lastError = error instanceof Error ? error : new Error(String(error));
+      if (!isRetryableGatewayConnectError(lastError) || remainingMs <= 5_000) {
+        throw lastError;
+      }
+      logLiveStep(`gateway connect warmup retry ${attempt}: ${lastError.message}`);
+      await sleep(Math.min(1_000 * attempt, 5_000));
+    }
+  }
+
+  throw lastError ?? new Error("gateway connect timeout");
+}
+
+async function connectClientOnce(params: { url: string; token: string; timeoutMs?: number }) {
   const timeoutMs = params.timeoutMs ?? CONNECT_TIMEOUT_MS;
   return await new Promise<GatewayClient>((resolve, reject) => {
     let done = false;
+    let client: GatewayClient | undefined;
     const finish = (result: { client?: GatewayClient; error?: Error }) => {
       if (done) {
         return;
@@ -109,13 +140,16 @@ async function connectClient(params: { url: string; token: string; timeoutMs?: n
       done = true;
       clearTimeout(connectTimeout);
       if (result.error) {
+        if (client) {
+          void client.stopAndWait({ timeoutMs: 1_000 }).catch(() => {});
+        }
         reject(result.error);
         return;
       }
       resolve(result.client as GatewayClient);
     };
 
-    const client = new GatewayClient({
+    client = new GatewayClient({
       url: params.url,
       token: params.token,
       clientName: GATEWAY_CLIENT_NAMES.TEST,
@@ -138,25 +172,94 @@ async function connectClient(params: { url: string; token: string; timeoutMs?: n
   });
 }
 
-async function waitForAcpBackendHealthy(timeoutMs = 60_000): Promise<void> {
+function isRetryableGatewayConnectError(error: Error): boolean {
+  const message = error.message.toLowerCase();
+  return (
+    message.includes("gateway closed during connect (1000)") ||
+    message.includes("gateway connect timeout") ||
+    message.includes("gateway connect challenge timeout")
+  );
+}
+
+function isRetryableAcpBindWarmupText(texts: string[]): boolean {
+  const combined = texts.join("\n\n").toLowerCase();
+  return (
+    combined.includes("acp runtime backend is currently unavailable") ||
+    combined.includes("try again in a moment") ||
+    combined.includes("acp runtime backend is not configured") ||
+    combined.includes("acp dispatch is disabled")
+  );
+}
+
+function formatAssistantTextPreview(texts: string[], maxChars = 600): string {
+  const combined = texts.join("\n\n").trim();
+  if (!combined) {
+    return "<empty>";
+  }
+  if (combined.length <= maxChars) {
+    return combined;
+  }
+  return combined.slice(-maxChars);
+}
+
+async function bindConversationAndWait(params: {
+  client: GatewayClient;
+  sessionKey: string;
+  liveAgent: "claude" | "codex";
+  originatingChannel: string;
+  originatingTo: string;
+  originatingAccountId: string;
+  timeoutMs?: number;
+}): Promise<{ mainAssistantTexts: string[]; spawnedSessionKey: string }> {
+  const timeoutMs = params.timeoutMs ?? 90_000;
   const startedAt = Date.now();
+  let attempt = 0;
+
   while (Date.now() - startedAt < timeoutMs) {
+    attempt += 1;
     const backend = getAcpRuntimeBackend("acpx");
-    if (backend?.healthy?.() ?? false) {
-      return;
-    }
     const runtime = backend?.runtime as { probeAvailability?: () => Promise<void> } | undefined;
     if (runtime?.probeAvailability) {
       await runtime.probeAvailability().catch(() => {});
-      if (backend?.healthy?.() ?? false) {
-        return;
-      }
-    } else if (backend && !backend.healthy) {
-      return;
     }
-    await sleep(250);
+    if (!(backend?.healthy?.() ?? false)) {
+      logLiveStep(`acpx backend still unhealthy before bind attempt ${attempt}`);
+      await sleep(5_000);
+      continue;
+    }
+
+    await sendChatAndWait({
+      client: params.client,
+      sessionKey: params.sessionKey,
+      idempotencyKey: `idem-bind-${randomUUID()}`,
+      message: `/acp spawn ${params.liveAgent} --bind here`,
+      originatingChannel: params.originatingChannel,
+      originatingTo: params.originatingTo,
+      originatingAccountId: params.originatingAccountId,
+    });
+
+    const mainHistory = await params.client.request<{ messages?: unknown[] }>("chat.history", {
+      sessionKey: params.sessionKey,
+      limit: 16,
+    });
+    const mainAssistantTexts = extractAssistantTexts(mainHistory.messages ?? []);
+    const spawnedSessionKey = extractSpawnedAcpSessionKey(mainAssistantTexts);
+    if (
+      mainAssistantTexts.join("\n\n").includes("Bound this conversation to") &&
+      spawnedSessionKey
+    ) {
+      return { mainAssistantTexts, spawnedSessionKey };
+    }
+    if (!isRetryableAcpBindWarmupText(mainAssistantTexts)) {
+      throw new Error(
+        `bind command did not produce an ACP session: ${formatAssistantTextPreview(mainAssistantTexts)}`,
+      );
+    }
+    logLiveStep(`acpx backend still warming up; retrying bind (${attempt})`);
+    await sleep(5_000);
   }
-  throw new Error("timed out waiting for the acpx runtime backend to become healthy");
+
+  throw new Error("timed out waiting for the ACP bind command to succeed");
 }
 
 async function waitForAgentRunOk(
@@ -301,32 +404,17 @@ describeLive("gateway live (ACP bind)", () => {
       logLiveStep("gateway websocket connected");
 
       try {
-        logLiveStep("waiting for acpx backend health");
-        await waitForAcpBackendHealthy();
-        logLiveStep("acpx backend healthy");
-
-        await sendChatAndWait({
+        const { mainAssistantTexts, spawnedSessionKey } = await bindConversationAndWait({
           client,
           sessionKey: originalSessionKey,
-          idempotencyKey: `idem-bind-${randomUUID()}`,
-          message: `/acp spawn ${liveAgent} --bind here`,
+          liveAgent,
           originatingChannel: "slack",
           originatingTo: conversationId,
           originatingAccountId: accountId,
         });
         logLiveStep("bind command completed");
-
-        const mainHistory = await client.request<{ messages?: unknown[] }>("chat.history", {
-          sessionKey: originalSessionKey,
-          limit: 12,
-        });
-        const mainAssistantTexts = extractAssistantTexts(mainHistory.messages ?? []);
-        const spawnedSessionKey = extractSpawnedAcpSessionKey(mainAssistantTexts);
         expect(mainAssistantTexts.join("\n\n")).toContain("Bound this conversation to");
         expect(spawnedSessionKey).toMatch(new RegExp(`^agent:${liveAgent}:acp:`));
-        if (!spawnedSessionKey) {
-          throw new Error("bind response did not expose the spawned ACP session key");
-        }
         logLiveStep(`binding announced for session ${spawnedSessionKey ?? "missing"}`);
 
         await sendChatAndWait({