diff --git a/test/trigger-busy-chain-stall.test.js b/test/trigger-busy-chain-stall.test.js
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+++ b/test/trigger-busy-chain-stall.test.js
@@ -0,0 +1,148 @@
+// test/trigger-busy-chain-stall.test.js
+//
+// Issue #360: a chain stalls after step 0 while the CLI descriptor stays
+// "busy" because background agents run, although the turn is over and the
+// session transcript says so. End to end through the real watcher and the
+// real trigger context, with the transcript as a file on disk.
+'use strict';
+
+process.env.SWITCHBOARD_SUBMIT_ENTER_DELAY_MS = '1';
+process.env.SWITCHBOARD_SUBMIT_VERIFY_MS = '400';
+process.env.SWITCHBOARD_BUSY_FALL_SETTLE_MS = '50';
+process.env.SWITCHBOARD_BUSY_RISE_WAIT_MS = '100';
+process.env.SWITCHBOARD_TRANSCRIPT_QUIET_MS = '300';
+
+const test   = require('node:test');
+const assert = require('node:assert/strict');
+const fs     = require('fs');
+const os     = require('os');
+const path   = require('path');
+
+const { start } = require('../trigger-watcher');
+const { createTriggerContext } = require('../trigger-context');
+
+function mkTmp(prefix) {
+  return fs.realpathSync.native(fs.mkdtempSync(path.join(os.tmpdir(), prefix)));
+}
+
+const iso = (ms) => new Date(ms).toISOString();
+const jsonl = (entries) => entries.map((e) => JSON.stringify(e)).join('\n') + '\n';
+const prompt = (at, content) => ({ type: 'user', timestamp: iso(at), message: { role: 'user', content } });
+const endTurn = (at) => ({ type: 'assistant', timestamp: iso(at), message: { role: 'assistant', stop_reason: 'end_turn', content: [{ type: 'text', text: 'x' }] } });
+const system = (at, subtype, extra = {}) => ({ type: 'system', subtype, timestamp: iso(at), ...extra });
+const enqueue = (at, content) => ({ type: 'queue-operation', operation: 'enqueue', content, timestamp: iso(at) });
+const dequeue = (at) => ({ type: 'queue-operation', operation: 'dequeue', timestamp: iso(at) });
+
+// What a turn answered while background agents keep the descriptor busy
+// leaves: the queued prompt, the answer, then the Stop hook and turn_duration.
+function closedTurn(command, delayMs) {
+  return (append) => {
+    append([enqueue(Date.now(), command), dequeue(Date.now()), prompt(Date.now(), command)]);
+    setTimeout(() => append([endTurn(Date.now()), system(Date.now(), 'stop_hook_summary'), system(Date.now(), 'turn_duration')]), delayMs);
+  };
+}
+
+// What /compact leaves, written only when compaction ends (synthetic text).
+function compactionOutput(enterAt) {
+  const done = Date.now();
+  return [
+    system(done + 800, 'compact_boundary', { compactMetadata: { trigger: 'manual', preTokens: 1 } }),
+    { type: 'user', isCompactSummary: true, isVisibleInTranscriptOnly: true, timestamp: iso(done), message: { role: 'user', content: 'This session is being continued. Synthetic summary.' } },
+    { type: 'user', isMeta: true, timestamp: iso(enterAt), message: { role: 'user', content: '<local-command-caveat>Caveat: synthetic.</local-command-caveat>' } },
+    prompt(enterAt, '<command-name>/compact</command-name>\n            <command-message>compact</command-message>\n            <command-args></command-args>'),
+    prompt(done + 900, '<local-command-stdout>Compacted</local-command-stdout>'),
+    { type: 'attachment', timestamp: iso(done + 100), attachment: { type: 'file' } },
+  ];
+}
+
+function busySession(sessionId, onEnter) {
+  const projectsDir = mkTmp('sw-busy-stall-projects-');
+  fs.mkdirSync(path.join(projectsDir, 'C--proj'));
+  const file = path.join(projectsDir, 'C--proj', sessionId + '.jsonl');
+  const old = Date.now() - 60_000;
+  fs.writeFileSync(file, jsonl([prompt(old - 1000, 'earlier'), endTurn(old), system(old + 100, 'turn_duration')]));
+  const past = new Date(old + 200);
+  fs.utimesSync(file, past, past);
+
+  const written = [];
+  let lastText = null;
+  const desc = { status: 'busy', statusUpdatedAt: Date.now() - 30_000 };
+  const append = (entries) => {
+    if (fs.existsSync(projectsDir)) fs.appendFileSync(file, jsonl(entries));
+  };
+  const session = {
+    pty: {
+      pid: process.pid,
+      write(data) {
+        written.push({ data, at: Date.now() });
+        if (data !== '\r') lastText = data;
+        if (data === '\r') onEnter({ append, command: lastText, n: written.filter((w) => w.data === '\r').length });
+      },
+    },
+    projectFolder: 'C--proj',
+    _cliBusy: true,
+    composerState: { pending: 0, lastInputAt: 0 },
+  };
+  const ctx = createTriggerContext({
+    activeSessions: new Map([[sessionId, session]]),
+    log: { info() {}, warn() {}, error() {}, debug() {} },
+    isPtyAlive: () => true,
+    getCliStatus: () => ({ ...desc }),
+    projectsDir,
+  });
+  return { ctx, written, cleanup: () => fs.rmSync(projectsDir, { recursive: true, force: true }) };
+}
+
+async function runChain(chain, s, uuid, timeoutMs) {
+  const tmp = mkTmp('sw-busy-stall-triggers-');
+  process.env.SWITCHBOARD_TRIGGERS_DIR = tmp;
+  const watcher = start(s.ctx);
+  try {
+    fs.writeFileSync(path.join(tmp, uuid + '.json'),
+      JSON.stringify({ sessionId: uuid, wait: 'none', chain, timeout_ms: timeoutMs }), 'utf8');
+    const resultPath = path.join(tmp, 'processed', uuid + '.result.json');
+    const deadline = Date.now() + timeoutMs + 5000;
+    while (!fs.existsSync(resultPath)) {
+      if (Date.now() > deadline) throw new Error('no result file');
+      await new Promise((r) => setTimeout(r, 20));
+    }
+    await new Promise((r) => setTimeout(r, 20));
+    return JSON.parse(fs.readFileSync(resultPath, 'utf8'));
+  } finally {
+    watcher.close();
+    delete process.env.SWITCHBOARD_TRIGGERS_DIR;
+    fs.rmSync(tmp, { recursive: true, force: true });
+  }
+}
+
+test('#360: a descriptor held busy by background agents, the turn closed in the transcript -> step 1 is written', async () => {
+  const uuid = 'sess-busy-stall-' + Date.now();
+  const s = busySession(uuid, ({ append, command }) => closedTurn(command, 100)(append));
+  try {
+    const result = await runChain([{ command: 'first step' }, { command: 'second step' }], s, uuid, 6000);
+
+    assert.ok(s.written.some((w) => w.data === 'second step'), 'step 1 was never written: ' + JSON.stringify(result));
+    assert.equal(result.ok, true);
+    assert.equal(result.steps[0].submit_confirmed, true);
+  } finally {
+    s.cleanup();
+  }
+});
+
+test('#360: /compact under a descriptor held busy, its output written when compaction ends -> step 1 is written', async () => {
+  const uuid = 'sess-busy-stall-compact-' + Date.now();
+  const s = busySession(uuid, ({ append, command, n }) => {
+    const enterAt = Date.now();
+    if (n === 1) setTimeout(() => append(compactionOutput(enterAt)), 3000);
+    else closedTurn(command, 100)(append);
+  });
+  try {
+    const result = await runChain([{ command: '/compact' }, { command: 'second step' }], s, uuid, 10000);
+
+    assert.ok(s.written.some((w) => w.data === 'second step'), 'step 1 was never written after /compact: ' + JSON.stringify(result));
+    assert.equal(result.ok, true);
+    assert.equal(result.steps[0].submit_confirmed, true);
+  } finally {
+    s.cleanup();
+  }
+});