diff --git a/docs/gateway.md b/docs/gateway.md
index add12c3e2..01424c2dd 100644
--- a/docs/gateway.md
+++ b/docs/gateway.md
@@ -24,6 +24,7 @@ pnpm clawdis gateway --force
 - Logs to stdout; use launchd/systemd to keep it alive and rotate logs.
 - Pass `--verbose` to mirror debug logging (handshakes, req/res, events) from the log file into stdio when troubleshooting.
 - `--force` uses `lsof` to find listeners on the chosen port, sends SIGTERM, logs what it killed, then starts the gateway (fails fast if `lsof` is missing).
+- If you run under a supervisor (launchd/systemd/mac app child-process mode), a stop/restart typically sends **SIGTERM**; older builds may surface this as `pnpm` `ELIFECYCLE` exit code **143** (SIGTERM), which is a normal shutdown, not a crash.
 - Optional shared secret: pass `--token <value>` or set `CLAWDIS_GATEWAY_TOKEN` to require clients to send `hello.auth.token`.
 
 ## Remote access
diff --git a/src/cli/program.ts b/src/cli/program.ts
index 2e4e140ab..481303e8c 100644
--- a/src/cli/program.ts
+++ b/src/cli/program.ts
@@ -269,8 +269,53 @@ Examples:
       if (opts.token) {
         process.env.CLAWDIS_GATEWAY_TOKEN = String(opts.token);
       }
+
+      let server: Awaited<ReturnType<typeof startGatewayServer>> | null = null;
+      let shuttingDown = false;
+      let forceExitTimer: ReturnType<typeof setTimeout> | null = null;
+
+      const onSigterm = () => shutdown("SIGTERM");
+      const onSigint = () => shutdown("SIGINT");
+
+      const shutdown = (signal: string) => {
+        // Ensure we don't leak listeners across restarts/tests.
+        process.removeListener("SIGTERM", onSigterm);
+        process.removeListener("SIGINT", onSigint);
+
+        if (shuttingDown) {
+          defaultRuntime.log(
+            info(`gateway: received ${signal} during shutdown; exiting now`),
+          );
+          defaultRuntime.exit(0);
+        }
+        shuttingDown = true;
+        defaultRuntime.log(info(`gateway: received ${signal}; shutting down`));
+
+        // Avoid hanging forever if a provider task ignores abort.
+        forceExitTimer = setTimeout(() => {
+          defaultRuntime.error(
+            "gateway: shutdown timed out; exiting without full cleanup",
+          );
+          defaultRuntime.exit(0);
+        }, 5000);
+
+        void (async () => {
+          try {
+            await server?.close();
+          } catch (err) {
+            defaultRuntime.error(`gateway: shutdown error: ${String(err)}`);
+          } finally {
+            if (forceExitTimer) clearTimeout(forceExitTimer);
+            defaultRuntime.exit(0);
+          }
+        })();
+      };
+
+      process.once("SIGTERM", onSigterm);
+      process.once("SIGINT", onSigint);
+
       try {
-        await startGatewayServer(port, { webchatPort });
+        server = await startGatewayServer(port, { webchatPort });
       } catch (err) {
         if (err instanceof GatewayLockError) {
           defaultRuntime.error(`Gateway failed to start: ${err.message}`);
diff --git a/src/gateway/server.test.ts b/src/gateway/server.test.ts
index 0dbd41a9f..bbfa07169 100644
--- a/src/gateway/server.test.ts
+++ b/src/gateway/server.test.ts
@@ -157,7 +157,10 @@ describe("gateway server", () => {
         },
       }),
     );
-    await onceMessage(ws, (o) => o.type === "res" && o.id === "agent-last-stale");
+    await onceMessage(
+      ws,
+      (o) => o.type === "res" && o.id === "agent-last-stale",
+    );
 
     const spy = vi.mocked(agentCommand);
     expect(spy).toHaveBeenCalled();
diff --git a/src/gateway/server.ts b/src/gateway/server.ts
index 06d5ec295..b8d4867a3 100644
--- a/src/gateway/server.ts
+++ b/src/gateway/server.ts
@@ -34,9 +34,9 @@ import { monitorWebProvider, webAuthExists } from "../providers/web/index.js";
 import { defaultRuntime } from "../runtime.js";
 import { monitorTelegramProvider } from "../telegram/monitor.js";
 import { sendMessageTelegram } from "../telegram/send.js";
+import { normalizeE164 } from "../utils.js";
 import { sendMessageWhatsApp } from "../web/outbound.js";
 import { ensureWebChatServerFromConfig } from "../webchat/server.js";
-import { normalizeE164 } from "../utils.js";
 import { buildMessageWithAttachments } from "./chat-attachments.js";
 import {
   ErrorCodes,
diff --git a/src/web/auto-reply.test.ts b/src/web/auto-reply.test.ts
index 0a503cb99..9b6285dad 100644
--- a/src/web/auto-reply.test.ts
+++ b/src/web/auto-reply.test.ts
@@ -244,9 +244,16 @@ describe("partial reply gating", () => {
       replyResolver,
     );
 
-    const stored = JSON.parse(await fs.readFile(store.storePath, "utf8")) as {
-      main?: { lastChannel?: string; lastTo?: string };
-    };
+    let stored: { main?: { lastChannel?: string; lastTo?: string } } | null =
+      null;
+    for (let attempt = 0; attempt < 50; attempt += 1) {
+      stored = JSON.parse(await fs.readFile(store.storePath, "utf8")) as {
+        main?: { lastChannel?: string; lastTo?: string };
+      };
+      if (stored.main?.lastChannel && stored.main?.lastTo) break;
+      await new Promise((resolve) => setTimeout(resolve, 5));
+    }
+    if (!stored) throw new Error("store not loaded");
     expect(stored.main?.lastChannel).toBe("whatsapp");
     expect(stored.main?.lastTo).toBe("+1000");
 
diff --git a/src/web/auto-reply.ts b/src/web/auto-reply.ts
index e762f4b52..4d34a0db8 100644
--- a/src/web/auto-reply.ts
+++ b/src/web/auto-reply.ts
@@ -752,6 +752,7 @@ export async function monitorWebProvider(
     // Batch inbound messages per conversation while command queue is busy.
     type PendingBatch = { messages: WebInboundMsg[]; timer?: NodeJS.Timeout };
     const pendingBatches = new Map<string, PendingBatch>();
+    const backgroundTasks = new Set<Promise<unknown>>();
 
     const buildLine = (msg: WebInboundMsg) => {
       // Build message prefix: explicit config > default based on allowFrom
@@ -863,7 +864,7 @@ export async function monitorWebProvider(
           return normalizeE164(latest.from);
         })();
         if (to) {
-          void updateLastRoute({
+          const task = updateLastRoute({
             storePath,
             sessionKey: mainKey,
             channel: "whatsapp",
@@ -874,6 +875,10 @@ export async function monitorWebProvider(
               "failed updating last route",
             );
           });
+          backgroundTasks.add(task);
+          task.finally(() => {
+            backgroundTasks.delete(task);
+          });
         }
       }
 
@@ -1053,6 +1058,10 @@ export async function monitorWebProvider(
       if (heartbeat) clearInterval(heartbeat);
       if (replyHeartbeatTimer) clearInterval(replyHeartbeatTimer);
       if (watchdogTimer) clearInterval(watchdogTimer);
+      if (backgroundTasks.size > 0) {
+        await Promise.allSettled(backgroundTasks);
+        backgroundTasks.clear();
+      }
       try {
         await listener.close();
       } catch (err) {