diff --git a/src/cli-notify.ts b/src/cli-notify.ts
index af925bcd..5cdae57a 100644
--- a/src/cli-notify.ts
+++ b/src/cli-notify.ts
@@ -43,7 +43,14 @@ export const postJson: JsonPost = (apiUrl, apiPath, payload, timeoutMs = REQUEST
   const url = new URL(apiPath, apiUrl);
   const body = JSON.stringify(payload);
   const transport = url.protocol === 'https:' ? https : http;
-  return new Promise((resolve) => {
+  return new Promise((resolveOnce) => {
+    // Settle once: a response that stalls after its headers ends in 'close' without 'end'.
+    let settled = false;
+    const resolve: typeof resolveOnce = (v) => {
+      if (settled) return;
+      settled = true;
+      resolveOnce(v);
+    };
     const headers: Record<string, string | number> = {
       Accept: 'application/json',
       'Content-Type': 'application/json',
@@ -64,6 +71,8 @@ export const postJson: JsonPost = (apiUrl, apiPath, payload, timeoutMs = REQUEST
       (res) => {
         let text = '';
         res.on('data', (c) => (text += c));
+        res.on('error', () => resolve({ status: 0 }));
+        res.on('close', () => resolve({ status: 0 }));
         res.on('end', () => {
           let error: string | undefined;
           let delivery: { ok: boolean; error?: string } | undefined;
diff --git a/src/discord-bridge.ts b/src/discord-bridge.ts
index dd39f2a5..85f3a442 100644
--- a/src/discord-bridge.ts
+++ b/src/discord-bridge.ts
@@ -655,6 +655,8 @@ export interface DiscordBridgeDeps {
    * Codeman types itself.
    */
   sendInput: (sessionId: string, text: string, fromUser: boolean) => Promise<boolean>;
+  /** True once the tab's agent has exited: tmux still accepts keys for a dead pane, so a tick would lie. */
+  agentExited?: (sessionId: string) => boolean;
   /** True while the session shows a permission or question dialog, which acts on a bare keypress. */
   awaitingChoice?: (sessionId: string) => boolean;
   /** A session's working folder, where received files are saved. Undefined when it is gone or remote. */
@@ -683,6 +685,8 @@ export class DiscordBridge {
   private held = false;
   /** Thread-map writes run one after another: concurrent creations must not interleave on the tmp file. */
   private persistChain: Promise<void> = Promise.resolve();
+  /** Per-thread chain of inbound messages (see onGatewayMessage). */
+  private inbound = new Map<string, Promise<void>>();
   private mapLoad?: Promise<void>;
   /** The first full load (config, thread map, gateway), shared by every caller that arrives before it ends. */
   private firstLoad?: Promise<void>;
@@ -711,6 +715,17 @@ export class DiscordBridge {
     await this.firstLoad;
   }
 
+  /** Forget thread entries for tabs that no longer exist (dropped without a delete, for example). Once, at boot. */
+  async prune(liveIds: Iterable<string>): Promise<void> {
+    await this.ensureLoaded();
+    const live = new Set(liveIds);
+    if (live.size === 0) return; // nothing restored: more likely a failed restore than an empty server
+    const stale = Object.keys(this.threads).filter((id) => !live.has(id));
+    if (stale.length === 0) return;
+    for (const id of stale) delete this.threads[id];
+    await this.persistThreads();
+  }
+
   /** Hold the gateway back (boot): a reply must not arrive before the restored tabs exist. */
   hold(): void {
     this.held = true;
@@ -765,6 +780,7 @@ export class DiscordBridge {
     this.lastReply.clear();
     this.names.clear();
     this.fresh.clear();
+    this.inbound.clear();
   }
 
   private fail(err: unknown): DiscordResult {
@@ -991,8 +1007,17 @@ export class DiscordBridge {
     };
   }
 
-  /** Inbound reply. Every gate here drops silently: a stranger learns nothing. */
+  /** Inbound reply. One chain per thread, so a reply that waits on a file download cannot be overtaken by a later one. */
   async onGatewayMessage(m: GatewayMessage): Promise<void> {
+    const key = String(m.channel_id);
+    const run = (this.inbound.get(key) ?? Promise.resolve()).then(() => this.handleMessage(m)).catch(() => undefined);
+    this.inbound.set(key, run);
+    await run;
+    if (this.inbound.get(key) === run) this.inbound.delete(key);
+  }
+
+  /** Every gate here drops silently: a stranger learns nothing. */
+  private async handleMessage(m: GatewayMessage): Promise<void> {
     if (!this.cfg.enabled || m.author?.bot) return;
     if (m.guild_id !== this.cfg.guildId) return;
     if (!this.cfg.allowedUserIds.includes(m.author?.id)) return;
@@ -1005,6 +1030,10 @@ export class DiscordBridge {
       await this.api.react(m.channel_id, m.id, '⏳').catch(() => undefined);
       return;
     }
+    if (this.deps.agentExited?.(sessionId)) {
+      await this.say(m.channel_id, 'The agent in that tab has exited, so nothing was typed.');
+      return;
+    }
     this.lastReply.set(sessionId, t);
     const saved = await this.saveAttachments(sessionId, m);
     const text = sanitiseReply(m.content ?? '', saved.paths);
diff --git a/src/web/server.ts b/src/web/server.ts
index 527f1d02..734c8597 100644
--- a/src/web/server.ts
+++ b/src/web/server.ts
@@ -520,6 +520,7 @@ export class WebServer extends EventEmitter {
       if (await session.writeViaMux(text, { fromUser }).catch(() => false)) return true;
       return session.write(text, { fromUser });
     },
+    agentExited: (id) => !!this.sessions.get(id)?.paneExit,
     awaitingChoice: (id) => approvalInbox.listPending().some((item) => item.sessionId === id && item.kind !== 'idle'),
     // Remote (ssh) sessions keep their folder on another host, so received files have nowhere local to go.
     sessionDir: (sessionId) => {
@@ -3258,7 +3259,10 @@ export class WebServer extends EventEmitter {
       if (restoredMail > 0) console.log(`[AgentInbox] restored ${restoredMail} pending message(s)`);
       const restored = await this.restoreMuxSessions();
       await this.finalizeRestoredState(restored);
-      void this.discordBridge.release().catch(() => undefined);
+      void this.discordBridge
+        .release()
+        .then(() => this.discordBridge.prune(this.sessions.keys()))
+        .catch(() => undefined);
 
       // Instance-scoped reaper: after restore, `docker rm -f` managed containers of
       // THIS instance whose case is gone from docker-cases.json (best-effort, never
diff --git a/test/cli-notify.test.ts b/test/cli-notify.test.ts
index a1e6ad3d..5127cf54 100644
--- a/test/cli-notify.test.ts
+++ b/test/cli-notify.test.ts
@@ -71,6 +71,21 @@ describe('runNotify', () => {
     }
   });
 
+  it('postJson settles when the server sends headers and then stalls the body', async () => {
+    const server = createServer((_req, res) => {
+      res.writeHead(200, { 'Content-Type': 'application/json', 'Content-Length': '500' });
+      res.write('{"success":');
+    });
+    await new Promise<void>((r) => server.listen(0, '127.0.0.1', r));
+    try {
+      const { port } = server.address() as AddressInfo;
+      expect((await postJson(`http://127.0.0.1:${port}`, '/x', {}, 100)).status).toBe(0);
+    } finally {
+      server.closeAllConnections();
+      server.close();
+    }
+  });
+
   it('treats a disabled bridge (409) as success that says so', async () => {
     const r = await runNotify({ message: 'x' }, ENV, '/work', fake(409));
     expect(r.code).toBe(0);
diff --git a/test/discord-bridge.test.ts b/test/discord-bridge.test.ts
index 376f244c..0ec6e008 100644
--- a/test/discord-bridge.test.ts
+++ b/test/discord-bridge.test.ts
@@ -551,6 +551,17 @@ describe('DiscordBridge', () => {
     b.stop();
   });
 
+  it('prune drops thread entries for tabs that no longer exist, and keeps the live ones', async () => {
+    const b = bridge();
+    await b.notify(MSG);
+    await b.notify({ ...MSG, sessionId: 's2', sessionName: 'w2' });
+    await b.prune(['s2']);
+    expect(Object.keys(await readThreadMap(dir))).toEqual(['s2']);
+    await b.prune([]); // nothing restored: leave the map alone
+    expect(Object.keys(await readThreadMap(dir))).toEqual(['s2']);
+    b.stop();
+  });
+
   describe('sendTest', () => {
     it('posts with the config it is given and leaves the live config alone', async () => {
       const auth: string[] = [];
@@ -734,7 +745,8 @@ describe('DiscordBridge files and startup hint', () => {
   function make(
     cfg: Partial<DiscordConfig> = {},
     dirFor: (id: string) => string | undefined = () => work,
-    awaitingChoice?: (id: string) => boolean
+    awaitingChoice?: (id: string) => boolean,
+    agentExited?: (id: string) => boolean
   ) {
     const b = new DiscordBridge({
       configDir: dir,
@@ -751,6 +763,7 @@ describe('DiscordBridge files and startup hint', () => {
       sendInput: async (id, text, fromUser) => (sent.push([id, text, fromUser]), true),
       sessionDir: dirFor,
       awaitingChoice,
+      agentExited,
       socketFactory: () => new FakeSocket(),
       now: () => t,
       sleep: async () => undefined,
@@ -834,6 +847,26 @@ describe('DiscordBridge files and startup hint', () => {
     b.stop();
   });
 
+  it('says the agent has exited and types nothing when the tab reports it', async () => {
+    const b = await make({}, undefined, undefined, () => true);
+    await b.onGatewayMessage(reply({ content: 'hello', attachments: [] }));
+    expect(sent).toHaveLength(0);
+    expect(String(posted.at(-1)?.body?.content)).toMatch(/exited/);
+    expect(posted.some((p) => p.path.includes('reactions'))).toBe(false);
+    b.stop();
+  });
+
+  it('types a reply that waits on a download before a later text reply', async () => {
+    const b = await make();
+    const slow = b.onGatewayMessage(reply({ content: 'first' }));
+    await new Promise((r) => setTimeout(r, 0)); // the first reply is under way (gate passed) before the clock moves
+    t += 5_000;
+    const fast = b.onGatewayMessage(reply({ id: '555555555555555556', content: 'second', attachments: [] }));
+    await Promise.all([slow, fast]);
+    expect(sent.map((s) => s[1].split(' ')[0])).toEqual(['first', 'second\r']);
+    b.stop();
+  });
+
   it('types a lone digit without Enter while a dialog is waiting, and with Enter otherwise', async () => {
     let waiting = true;
     const b = await make({}, undefined, () => waiting);
diff --git a/test/discord-push-glue.test.ts b/test/discord-push-glue.test.ts
index 96d1e9c9..e062e4d9 100644
--- a/test/discord-push-glue.test.ts
+++ b/test/discord-push-glue.test.ts
@@ -43,6 +43,20 @@ function server(): Internals {
 
 beforeEach(() => sendNotification.mockClear());
 
+describe('bridge deps', () => {
+  it('agentExited is true only for a session whose pane exit was observed', () => {
+    const s = new WebServer(0, false, true, '127.0.0.1', 'box') as unknown as Internals & {
+      discordBridge: { deps: { agentExited: (id: string) => boolean } };
+    };
+    s.sessions.set('dead', { paneExit: { observedAt: 1 } });
+    s.sessions.set('alive', {});
+    const { agentExited } = s.discordBridge.deps;
+    expect(agentExited('dead')).toBe(true);
+    expect(agentExited('alive')).toBe(false);
+    expect(agentExited('missing')).toBe(false);
+  });
+});
+
 describe('sendPushNotifications -> Discord', () => {
   it('posts a permission prompt with zero push subscriptions, with the rendered screen as the tail', async () => {
     const s = server();