openryoko 2026.8.4 → 2026.8.6

package/dist/bin/jimmy.js

@@ -159,6 +159,69 @@ program
         await runConfigInteractive(value);
     });
 }
+// 切り離しジョブ（ryoko job run / list — 完了時にセッションを自動起床）
+{
+    const jobCmd = program
+        .command("job")
+        .description("切り離しバックグラウンドジョブ（完了時に元セッションを自動起床）");
+    jobCmd
+        .command("run")
+        .description("コマンドを切り離して実行し、終了時（成功/失敗とも）にセッションへ通知する")
+        .requiredOption("--name <name>", "ジョブ名（通知・ログの識別子）")
+        .requiredOption("--session <id>", "終了時に起こすセッションID")
+        .option("--timeout <sec>", "この秒数を超えたらジョブをkillして失敗通知する")
+        .option("--log <path>", "ログファイルのパス（省略時は ~/.ryoko/jobs/logs/<id>.log）")
+        .option("--gateway <url>", "gateway URL（loopbackのみ許可。省略時はconfigのポート）")
+        .argument("<command...>", "実行するシェルコマンド。クォートした1つの文字列で渡すこと（例: -- 'cd /x && make'）")
+        .action(async (commandParts, opts) => {
+        let timeoutSec;
+        if (opts.timeout !== undefined) {
+            timeoutSec = Number(opts.timeout);
+            if (!Number.isFinite(timeoutSec) || timeoutSec <= 0) {
+                console.error(`--timeout must be a positive number of seconds (got "${opts.timeout}")`);
+                process.exit(1);
+            }
+        }
+        const { launchDetachedJob } = await import("../src/jobs/run.js");
+        const state = launchDetachedJob({
+            name: opts.name,
+            sessionId: opts.session,
+            command: commandParts.join(" "),
+            gatewayUrl: opts.gateway,
+            logFile: opts.log,
+            timeoutSec,
+        });
+        console.log(`Detached job started: ${state.id}`);
+        console.log(`  log:     ${state.logFile}`);
+        console.log(`  monitor: pid ${state.monitorPid}`);
+        console.log(`  wakes:   session ${state.sessionId} on exit (success or failure)`);
+        console.log(`This turn can end now — the job survives it and will wake the session when done.`);
+    });
+    jobCmd
+        .command("list")
+        .description("ジョブの状態を一覧表示する")
+        .action(async () => {
+        const { listJobStates, isPidAlive } = await import("../src/jobs/state.js");
+        const states = listJobStates();
+        if (states.length === 0) {
+            console.log("No jobs.");
+            return;
+        }
+        for (const s of states) {
+            const orphaned = s.status === "running" && !isPidAlive(s.monitorPid) ? " (ORPHANED — monitor dead)" : "";
+            const exit = s.exitCode !== undefined && s.exitCode !== null ? ` exit=${s.exitCode}` : s.timedOut ? " timed-out" : "";
+            console.log(`${s.id}  [${s.status}${orphaned}]${exit}  session=${s.sessionId}  log=${s.logFile}`);
+        }
+    });
+    jobCmd
+        .command("_monitor <id>", { hidden: true })
+        .description("内部用: 切り離しモニタープロセスの本体")
+        .option("--jobs-dir <dir>")
+        .action(async (id, opts) => {
+        const { runJobMonitor } = await import("../src/jobs/monitor.js");
+        await runJobMonitor(id, { jobsDir: opts.jobsDir });
+    });
+}
 program
     .command("chrome-allow")
     .description("Claude Chrome拡張で全サイトを事前承認する")

package/dist/bin/jimmy.js.map

@@ -1 +1 @@
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package/dist/package.json

@@ -1,6 +1,6 @@
 {
     "name": "openryoko",
-    "version": "2026.8.4",
+    "version": "2026.8.6",
     "description": "OpenRyoko — Slackで空気を読んで働くAIアシスタント・ゲートウェイ（Jinnベース、Claude Code/Codex/Gemini CLI対応）",
     "license": "MIT",
     "type": "module",

package/dist/src/gateway/__tests__/notification-wake-delivery.test.d.ts

@@ -0,0 +1,2 @@
+export {};
+//# sourceMappingURL=notification-wake-delivery.test.d.ts.map

package/dist/src/gateway/__tests__/notification-wake-delivery.test.d.ts.map

@@ -0,0 +1 @@
+{"version":3,"file":"notification-wake-delivery.test.d.ts","sourceRoot":"","sources":["../../../../src/gateway/__tests__/notification-wake-delivery.test.ts"],"names":[],"mappings":""}

package/dist/src/gateway/__tests__/notification-wake-delivery.test.js

@@ -0,0 +1,145 @@
+import { describe, it, expect, beforeAll, afterAll, vi } from "vitest";
+import fs from "node:fs";
+import http from "node:http";
+import os from "node:os";
+import path from "node:path";
+// Regression pin for issue #38 follow-up: a session woken by a notification
+// (detached job finished) runs on the gateway's connector-less web path. Its
+// final answer MUST come back to the original Slack channel/thread stored in
+// reply_context — the 2026-08-04 accident left an externally-shared customer
+// thread waiting on "生成中です" forever.
+//
+// RYOKO_HOME must point at a temp dir BEFORE any module import pulls in
+// shared/paths.js, so every module here is imported dynamically.
+process.env.RYOKO_HOME = fs.mkdtempSync(path.join(os.tmpdir(), "wake-test-home-"));
+const STUB_CONFIG = {
+    jinn: { version: "0.0.0" },
+    gateway: { port: 0, host: "127.0.0.1" },
+    engines: {
+        default: "claude",
+        claude: { bin: "claude", model: "" },
+        codex: { bin: "codex", model: "" },
+    },
+    connectors: {},
+    sessions: {},
+    logging: { level: "error", stdout: false, file: "" },
+};
+describe("notification wake-up delivers the reply to the origin connector", () => {
+    let server;
+    let baseUrl;
+    let replyMessage;
+    let sessionId;
+    beforeAll(async () => {
+        const { handleApiRequest } = await import("../api.js");
+        const { createSession } = await import("../../sessions/registry.js");
+        const { SessionManager } = await import("../../sessions/manager.js");
+        const engineRun = vi.fn(async () => ({
+            result: "資料が完成しました。アップロード済みです。",
+            sessionId: "engine-sess-1",
+            numTurns: 1,
+        }));
+        const mockEngine = { run: engineRun };
+        const engines = new Map([["claude", mockEngine]]);
+        const sessionManager = new SessionManager(STUB_CONFIG, engines, ["slack"]);
+        replyMessage = vi.fn(async () => "posted-ts");
+        const fakeSlack = {
+            name: "slack",
+            replyMessage,
+            addReaction: vi.fn(async () => { }),
+            getCapabilities: () => ({ threading: true, messageEdits: true, reactions: true, attachments: true }),
+            reconstructTarget: (rc) => ({
+                channel: typeof rc.channel === "string" ? rc.channel : "",
+                thread: typeof rc.thread === "string" ? rc.thread : undefined,
+                messageTs: typeof rc.messageTs === "string" ? rc.messageTs : undefined,
+            }),
+        };
+        const session = createSession({
+            engine: "claude",
+            source: "slack",
+            sourceRef: "C_EXTERNAL",
+            connector: "slack",
+            sessionKey: "slack:C_EXTERNAL:100.200",
+            replyContext: { channel: "C_EXTERNAL", thread: "100.200", messageTs: "100.300" },
+            transportMeta: { channelExternal: true },
+            prompt: "資料を作って",
+        });
+        sessionId = session.id;
+        const context = {
+            config: STUB_CONFIG,
+            getConfig: () => STUB_CONFIG,
+            sessionManager,
+            startTime: 0,
+            emit: () => { },
+            connectors: new Map([["slack", fakeSlack]]),
+        };
+        server = http.createServer((req, res) => {
+            // eslint-disable-next-line @typescript-eslint/no-explicit-any
+            handleApiRequest(req, res, context);
+        });
+        await new Promise((r) => server.listen(0, "127.0.0.1", r));
+        const addr = server.address();
+        baseUrl = typeof addr === "object" && addr ? `http://127.0.0.1:${addr.port}` : "";
+    });
+    afterAll(async () => {
+        await new Promise((resolve, reject) => server.close((e) => (e ? reject(e) : resolve())));
+        fs.rmSync(process.env.RYOKO_HOME, { recursive: true, force: true });
+    });
+    it("wakes the session and replies into the original channel/thread", async () => {
+        const res = await fetch(`${baseUrl}/api/sessions/${sessionId}/message`, {
+            method: "POST",
+            headers: { "content-type": "application/json" },
+            body: JSON.stringify({
+                message: '✅ Detached job "pdf-build" completed successfully (exit 0).',
+                role: "notification",
+            }),
+        });
+        expect(res.status).toBe(200);
+        // The engine run + delivery happen asynchronously after the 200.
+        await vi.waitFor(() => {
+            expect(replyMessage).toHaveBeenCalledTimes(1);
+        }, { timeout: 10_000 });
+        const [target, text] = replyMessage.mock.calls[0];
+        expect(target).toMatchObject({ channel: "C_EXTERNAL", thread: "100.200" });
+        expect(text).toBe("資料が完成しました。アップロード済みです。");
+    });
+    it("a duplicate dedupeKey does not enqueue a second turn (monitor retry after lost response)", async () => {
+        replyMessage.mockClear();
+        const body = JSON.stringify({
+            message: '✅ Detached job "dedupe-job" completed successfully (exit 0).',
+            role: "notification",
+            dedupeKey: "job:dedupe-job-1",
+        });
+        const first = await fetch(`${baseUrl}/api/sessions/${sessionId}/message`, {
+            method: "POST",
+            headers: { "content-type": "application/json" },
+            body,
+        });
+        expect(first.status).toBe(200);
+        expect((await first.json()).status).toBe("queued");
+        const second = await fetch(`${baseUrl}/api/sessions/${sessionId}/message`, {
+            method: "POST",
+            headers: { "content-type": "application/json" },
+            body,
+        });
+        expect(second.status).toBe(200);
+        expect((await second.json()).status).toBe("duplicate");
+        await vi.waitFor(() => {
+            expect(replyMessage).toHaveBeenCalledTimes(1); // one turn, one delivery
+        }, { timeout: 10_000 });
+        await new Promise((r) => setTimeout(r, 1000));
+        expect(replyMessage).toHaveBeenCalledTimes(1);
+    });
+    it("a plain user message on the web path does NOT auto-post to the connector", async () => {
+        replyMessage.mockClear();
+        const res = await fetch(`${baseUrl}/api/sessions/${sessionId}/message`, {
+            method: "POST",
+            headers: { "content-type": "application/json" },
+            body: JSON.stringify({ message: "operator typing in web UI", role: "user" }),
+        });
+        expect(res.status).toBe(200);
+        // Give the async run time to complete, then confirm no connector post.
+        await new Promise((r) => setTimeout(r, 1500));
+        expect(replyMessage).not.toHaveBeenCalled();
+    });
+});
+//# sourceMappingURL=notification-wake-delivery.test.js.map

package/dist/src/gateway/__tests__/notification-wake-delivery.test.js.map

@@ -0,0 +1 @@
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package/dist/src/gateway/__tests__/notification-wake-restart.test.d.ts

@@ -0,0 +1,2 @@
+export {};
+//# sourceMappingURL=notification-wake-restart.test.d.ts.map

package/dist/src/gateway/__tests__/notification-wake-restart.test.d.ts.map

@@ -0,0 +1 @@
+{"version":3,"file":"notification-wake-restart.test.d.ts","sourceRoot":"","sources":["../../../../src/gateway/__tests__/notification-wake-restart.test.ts"],"names":[],"mappings":""}

package/dist/src/gateway/__tests__/notification-wake-restart.test.js

@@ -0,0 +1,97 @@
+import { describe, it, expect, beforeAll, afterAll, vi } from "vitest";
+import fs from "node:fs";
+import os from "node:os";
+import path from "node:path";
+// Gateway-restart recovery for notification wake-ups (issue #38 follow-up):
+// the job monitor got its 200 (message persisted + queue item enqueued) and
+// will never re-send. If the gateway dies before running the turn, the resume
+// pass must replay the queue item FOR CONNECTOR-ORIGIN SESSIONS TOO — and
+// with origin-connector delivery, or the customer thread stays silent.
+process.env.RYOKO_HOME = fs.mkdtempSync(path.join(os.tmpdir(), "wake-restart-home-"));
+const STUB_CONFIG = {
+    jinn: { version: "0.0.0" },
+    gateway: { port: 0, host: "127.0.0.1" },
+    engines: {
+        default: "claude",
+        claude: { bin: "claude", model: "" },
+        codex: { bin: "codex", model: "" },
+    },
+    connectors: {},
+    sessions: {},
+    logging: { level: "error", stdout: false, file: "" },
+};
+describe("resumePendingWebQueueItems — connector-origin notification wake-ups", () => {
+    let replyMessage;
+    let engineRun;
+    beforeAll(async () => {
+        const { resumePendingWebQueueItems } = await import("../api.js");
+        const { createSession, insertMessage, enqueueQueueItem } = await import("../../sessions/registry.js");
+        const { SessionManager } = await import("../../sessions/manager.js");
+        engineRun = vi.fn(async () => ({ result: "遅れましたが完成しました", sessionId: "es-1", numTurns: 1 }));
+        const engines = new Map([["claude", { run: engineRun }]]);
+        const sessionManager = new SessionManager(STUB_CONFIG, engines, ["slack"]);
+        replyMessage = vi.fn(async () => "ts");
+        const fakeSlack = {
+            name: "slack",
+            replyMessage,
+            addReaction: vi.fn(async () => { }),
+            getCapabilities: () => ({ threading: true, messageEdits: true, reactions: true, attachments: true }),
+            reconstructTarget: (rc) => ({
+                channel: typeof rc.channel === "string" ? rc.channel : "",
+                thread: typeof rc.thread === "string" ? rc.thread : undefined,
+            }),
+        };
+        // Simulate the pre-restart state the monitor left behind: notification
+        // message persisted + queue item pending, but no turn ever ran.
+        const wakeText = '✅ Detached job "pdf" completed successfully (exit 0).';
+        const slackSession = createSession({
+            engine: "claude",
+            source: "slack",
+            sourceRef: "C_CUST",
+            connector: "slack",
+            sessionKey: "slack:C_CUST:1.2",
+            replyContext: { channel: "C_CUST", thread: "1.2" },
+            transportMeta: { channelExternal: true },
+            prompt: "資料を作って",
+        });
+        insertMessage(slackSession.id, "notification", wakeText);
+        enqueueQueueItem(slackSession.id, slackSession.sessionKey, wakeText);
+        // Control: a connector session with a pending USER prompt must stay
+        // untouched (pre-existing behavior — the connector route owns it).
+        const userSession = createSession({
+            engine: "claude",
+            source: "slack",
+            sourceRef: "C_OTHER",
+            connector: "slack",
+            sessionKey: "slack:C_OTHER:9.9",
+            replyContext: { channel: "C_OTHER", thread: "9.9" },
+            prompt: "こんにちは",
+        });
+        insertMessage(userSession.id, "user", "続きをやって");
+        enqueueQueueItem(userSession.id, userSession.sessionKey, "続きをやって");
+        const context = {
+            config: STUB_CONFIG,
+            getConfig: () => STUB_CONFIG,
+            sessionManager,
+            startTime: 0,
+            emit: () => { },
+            connectors: new Map([["slack", fakeSlack]]),
+        };
+        // eslint-disable-next-line @typescript-eslint/no-explicit-any
+        resumePendingWebQueueItems(context);
+    });
+    afterAll(() => {
+        fs.rmSync(process.env.RYOKO_HOME, { recursive: true, force: true });
+    });
+    it("replays the notification wake-up and delivers to the original thread", async () => {
+        await vi.waitFor(() => {
+            expect(replyMessage).toHaveBeenCalledTimes(1);
+        }, { timeout: 10_000 });
+        const [target, text] = replyMessage.mock.calls[0];
+        expect(target).toMatchObject({ channel: "C_CUST", thread: "1.2" });
+        expect(text).toBe("遅れましたが完成しました");
+        // Only the notification item ran — the user-prompt item was left alone.
+        expect(engineRun).toHaveBeenCalledTimes(1);
+    });
+});
+//# sourceMappingURL=notification-wake-restart.test.js.map

package/dist/src/gateway/__tests__/notification-wake-restart.test.js.map

@@ -0,0 +1 @@
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package/dist/src/gateway/api.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"api.d.ts","sourceRoot":"","sources":["../../../src/gateway/api.ts"],"names":[],"mappings":"AAAA,OAAO,KAAK,EAAE,eAAe,IAAI,WAAW,EAAE,cAAc,EAAE,MAAM,WAAW,CAAC;AAMhF,OAAO,KAAK,EAAoC,UAAU,EAAmB,MAAM,oBAAoB,CAAC;AAExG,OAAO,KAAK,EAAE,cAAc,EAAE,MAAM,wBAAwB,CAAC;AAuD7D,MAAM,WAAW,UAAU;IACzB,MAAM,EAAE,UAAU,CAAC;IACnB,cAAc,EAAE,cAAc,CAAC;IAC/B,SAAS,EAAE,MAAM,CAAC;IAClB,SAAS,EAAE,MAAM,UAAU,CAAC;IAC5B,IAAI,EAAE,CAAC,KAAK,EAAE,MAAM,EAAE,OAAO,EAAE,OAAO,KAAK,IAAI,CAAC;IAChD,UAAU,EAAE,GAAG,CAAC,MAAM,EAAE,OAAO,oBAAoB,EAAE,SAAS,CAAC,CAAC;IAChE,wBAAwB,CAAC,EAAE,MAAM,OAAO,CAAC;QAAE,OAAO,EAAE,MAAM,EAAE,CAAC;QAAC,OAAO,EAAE,MAAM,EAAE,CAAC;QAAC,MAAM,EAAE,MAAM,EAAE,CAAA;KAAE,CAAC,CAAC;IACrG;;;;OAIG;IACH,mBAAmB,CAAC,EAAE,MAAM,OAAO,CAAC;QAAE,OAAO,EAAE,MAAM,EAAE,CAAC;QAAC,OAAO,EAAE,MAAM,EAAE,CAAC;QAAC,MAAM,EAAE,MAAM,EAAE,CAAA;KAAE,CAAC,CAAC;IAChG;;;;;;OAMG;IACH,2BAA2B,CAAC,EAAE,MAAM,IAAI,CAAC;IACzC;;;;OAIG;IACH,gCAAgC,CAAC,EAAE,MAAM,IAAI,CAAC;IAC9C;;;;;OAKG;IACH,YAAY,CAAC,EAAE,OAAO,oBAAoB,EAAE,YAAY,CAAC;IACzD,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAED,wBAAgB,0BAA0B,CAAC,OAAO,EAAE,UAAU,GAAG,IAAI,CA4CpE;AAoMD,wBAAgB,SAAS,CAAC,MAAM,EAAE,MAAM,CAAC,MAAM,EAAE,OAAO,CAAC,EAAE,MAAM,EAAE,MAAM,CAAC,MAAM,EAAE,OAAO,CAAC,GAAG,MAAM,CAAC,MAAM,EAAE,OAAO,CAAC,CA+BnH;AA4CD,wBAAsB,gBAAgB,CACpC,GAAG,EAAE,WAAW,EAChB,GAAG,EAAE,cAAc,EACnB,OAAO,EAAE,UAAU,GAClB,OAAO,CAAC,IAAI,CAAC,CAoqDf"}

package/dist/src/gateway/api.js

@@ -5,8 +5,9 @@ import path from "node:path";
 import yaml from "js-yaml";
 import { isInterruptibleEngine } from "../shared/types.js";
 import { buildContext } from "../sessions/context.js";
-import { initDb, listSessions, getSession, createSession, updateSession, deleteSession, deleteSessions, duplicateSession, insertMessage, getMessages, enqueueQueueItem, cancelQueueItem, getQueueItems, cancelAllPendingQueueItems, listAllPendingQueueItems, getFile, } from "../sessions/registry.js";
+import { initDb, listSessions, getSession, createSession, updateSession, deleteSession, deleteSessions, duplicateSession, insertMessage, getMessages, enqueueQueueItem, insertNotificationWithQueueItem, cancelQueueItem, getQueueItems, cancelAllPendingQueueItems, listAllPendingQueueItems, getFile, } from "../sessions/registry.js";
 import { forkEngineSession } from "../sessions/fork.js";
+import { deliverToOriginConnector, isUndeliveredToOrigin, recordFailedOriginDelivery } from "../sessions/origin-delivery.js";
 import { CONFIG_PATH, CRON_RUNS, ORG_DIR, SKILLS_DIR, LOGS_DIR, TMP_DIR, FILES_DIR, } from "../shared/paths.js";
 import { logger } from "../shared/logger.js";
 import { getSttStatus, downloadModel, transcribe as sttTranscribe, resolveLanguages, WHISPER_LANGUAGES } from "../stt/stt.js";
@@ -37,8 +38,20 @@ export function resumePendingWebQueueItems(context) {
             cancelQueueItem(item.id);
             continue;
         }
-        if (session.source !== "web")
-            continue;
+        // Connector-origin sessions normally get their runs from the connector
+        // route, EXCEPT notification wake-ups (detached jobs, child callbacks):
+        // the job monitor already got its 200 and will never re-send, so a
+        // restart here would strand the wake-up forever. Detect those by the
+        // persisted notification message matching the queued prompt and resume
+        // them with origin-connector delivery.
+        let deliverToConnector = false;
+        if (session.source !== "web") {
+            const messages = getMessages(session.id);
+            const match = [...messages].reverse().find((m) => m.content === item.prompt);
+            if (match?.role !== "notification")
+                continue;
+            deliverToConnector = true;
+        }
         session = maybeRevertEngineOverride(session);
         const config = context.getConfig();
         const engine = context.sessionManager.getEngine(session.engine);
@@ -49,7 +62,7 @@ export function resumePendingWebQueueItems(context) {
         }
         // Ensure the session is in a runnable state
         updateSession(session.id, { status: "running", lastActivity: new Date().toISOString(), lastError: null });
-        dispatchWebSessionRun(session, item.prompt, engine, config, context, { queueItemId: item.id });
+        dispatchWebSessionRun(session, item.prompt, engine, config, context, { queueItemId: item.id, deliverToConnector });
         resumed++;
     }
     if (resumed > 0) {
@@ -96,11 +109,24 @@ function maybeRevertEngineOverride(session) {
         lastError: null,
     }) ?? session;
 }
+// In-memory idempotency keys for notification wake-ups. The persisted-message
+// comparison in the /message handler covers gateway restarts; this map covers
+// the common case cheaply and caps unbounded growth by TTL pruning on write.
+const seenDedupeKeys = new Map();
+const DEDUPE_TTL_MS = 60 * 60 * 1000;
+function rememberDedupeKey(key) {
+    const now = Date.now();
+    for (const [k, t] of seenDedupeKeys) {
+        if (now - t > DEDUPE_TTL_MS)
+            seenDedupeKeys.delete(k);
+    }
+    seenDedupeKeys.set(key, now);
+}
 function dispatchWebSessionRun(session, prompt, engine, config, context, opts) {
     const run = async () => {
         await context.sessionManager.getQueue().enqueue(session.sessionKey || session.sourceRef, async () => {
             context.emit("session:started", { sessionId: session.id });
-            await runWebSession(session, prompt, engine, config, context, opts?.attachments);
+            await runWebSession(session, prompt, engine, config, context, opts?.attachments, opts?.deliverToConnector);
         }, opts?.queueItemId);
     };
     const launch = () => {
@@ -740,12 +766,39 @@ export async function handleApiRequest(req, res, context) {
             // Allow internal callers (e.g. child session callbacks) to specify a non-user role
             const messageRole = body.role === "notification" ? "notification" : "user";
             const isNotification = messageRole === "notification";
+            // Notification wake-ups are a loopback-only mechanism (job monitors,
+            // child-session callbacks). A remote caller must not be able to wake an
+            // arbitrary session — the woken turn can post into its origin Slack
+            // conversation, so this would be a remote-to-customer-channel bridge.
+            if (isNotification && (!req.socket.remoteAddress || !HOOK_LOOPBACK.has(req.socket.remoteAddress))) {
+                return json(res, { error: "notification role is loopback-only" }, 403);
+            }
+            // Idempotency: a job monitor retries its wake-up when a response is
+            // lost after the gateway already accepted it. Same dedupeKey (+ an
+            // identical persisted notification, which survives restarts) → don't
+            // enqueue a second engine turn. The key is only REMEMBERED after the
+            // message + queue item are durably persisted below, so a failure
+            // before that point never turns the retry into a false duplicate.
+            const dedupeKey = typeof body.dedupeKey === "string" && body.dedupeKey.trim() ? body.dedupeKey.trim() : null;
+            const dedupedNotification = isNotification && dedupeKey !== null;
+            if (dedupedNotification) {
+                const duplicate = seenDedupeKeys.has(dedupeKey)
+                    || getMessages(session.id).some((m) => m.role === "notification" && m.content === prompt);
+                if (duplicate) {
+                    return json(res, { status: "duplicate", sessionId: session.id });
+                }
+            }
             const config = context.getConfig();
             const engine = context.sessionManager.getEngine(session.engine);
             if (!engine)
                 return serverError(res, `Engine "${session.engine}" not available`);
-            // Persist the message immediately
-            insertMessage(session.id, messageRole, prompt);
+            // Persist the message immediately. Deduped notifications defer this to
+            // the atomic message+queue-item write below — the duplicate check above
+            // treats "message exists" as "turn queued", so the two writes must
+            // never be separable by a crash.
+            if (!dedupedNotification) {
+                insertMessage(session.id, messageRole, prompt);
+            }
             // Emit notification event for UI display (renders as system banner, not user bubble)
             if (isNotification) {
                 context.emit("session:notification", { sessionId: session.id, message: prompt });
@@ -789,9 +842,20 @@ export async function handleApiRequest(req, res, context) {
             context.sessionManager.getQueue().clearCancelled(session.sessionKey || session.sourceRef || session.id);
             const attachmentPaths = resolveAttachmentPaths(body.attachments);
             const sessionKey = session.sessionKey || session.sourceRef || session.id;
-            const queueItemId = enqueueQueueItem(session.id, sessionKey, prompt);
+            const queueItemId = dedupedNotification
+                ? insertNotificationWithQueueItem(session.id, sessionKey, prompt)
+                : enqueueQueueItem(session.id, sessionKey, prompt);
+            if (dedupedNotification)
+                rememberDedupeKey(dedupeKey);
             context.emit("queue:updated", { sessionId: session.id, sessionKey });
-            dispatchWebSessionRun(session, prompt, engine, config, context, { queueItemId, attachments: attachmentPaths.length > 0 ? attachmentPaths : undefined });
+            dispatchWebSessionRun(session, prompt, engine, config, context, {
+                queueItemId,
+                attachments: attachmentPaths.length > 0 ? attachmentPaths : undefined,
+                // A notification wake-up (detached job finished, child callback) runs
+                // on this connector-less path; deliver the answer back to the origin
+                // conversation so e.g. a Slack thread is not left waiting silently.
+                deliverToConnector: isNotification,
+            });
             return json(res, { status: "queued", sessionId: session.id });
         }
         // GET /api/cron
@@ -2056,7 +2120,12 @@ function loadTranscriptMessages(engineSessionId) {
     }
     return [];
 }
-async function runWebSession(session, prompt, engine, config, context, attachments) {
+async function runWebSession(session, prompt, engine, config, context, attachments, 
+/** Deliver the final answer to the session's origin connector (Slack thread
+ *  etc.). Set for notification-triggered wake-ups: this run path has no
+ *  connector of its own, so without explicit delivery a woken Slack session
+ *  would compute its reply and post it nowhere (issue #38 follow-up). */
+deliverToConnector) {
     const currentSession = getSession(session.id);
     if (!currentSession) {
         logger.info(`Skipping deleted web session ${session.id} before run start`);
@@ -2260,6 +2329,11 @@ async function runWebSession(session, prompt, engine, config, context, attachmen
                     });
                     if (completedFallback) {
                         notifyParentSession(completedFallback, { result: fallbackResult.result, error: fallbackResult.error ?? null, cost: fallbackResult.cost, durationMs: fallbackResult.durationMs }, { alwaysNotify: employee?.alwaysNotify });
+                        if (deliverToConnector && fallbackResult.result && !fallbackResult.error) {
+                            const delivery = await deliverToOriginConnector(completedFallback, fallbackResult.result, context.connectors);
+                            if (isUndeliveredToOrigin(delivery, completedFallback))
+                                recordFailedOriginDelivery(completedFallback, context.emit);
+                        }
                     }
                     context.emit("session:completed", {
                         sessionId: currentSession.id,
@@ -2375,6 +2449,11 @@ async function runWebSession(session, prompt, engine, config, context, attachmen
                         notifyRateLimitResumed(completedAfterRetry);
                         notifyDiscordChannel(`✅ Claude usage limit cleared. Session ${currentSession.id}${currentSession.employee ? ` (${currentSession.employee})` : ""} resumed.`);
                         notifyParentSession(completedAfterRetry, { result: retryResult.result, error: retryResult.error ?? null, cost: retryResult.cost, durationMs: retryResult.durationMs }, { alwaysNotify: employee?.alwaysNotify });
+                        if (deliverToConnector && retryResult.result && !retryResult.error) {
+                            const delivery = await deliverToOriginConnector(completedAfterRetry, retryResult.result, context.connectors);
+                            if (isUndeliveredToOrigin(delivery, completedAfterRetry))
+                                recordFailedOriginDelivery(completedAfterRetry, context.emit);
+                        }
                     }
                     context.emit("session:completed", {
                         sessionId: currentSession.id,
@@ -2431,6 +2510,11 @@ async function runWebSession(session, prompt, engine, config, context, attachmen
         }
         if (completedSession) {
             notifyParentSession(completedSession, { result: result.result, error: result.error ?? null, cost: result.cost, durationMs: result.durationMs }, { alwaysNotify: employee?.alwaysNotify });
+            if (deliverToConnector && result.result && !result.error) {
+                const delivery = await deliverToOriginConnector(completedSession, result.result, context.connectors);
+                if (isUndeliveredToOrigin(delivery, completedSession))
+                    recordFailedOriginDelivery(completedSession, context.emit);
+            }
         }
         context.emit("session:completed", {
             sessionId: currentSession.id,