diff --git a/docs/automation/webhook.md b/docs/automation/webhook.md
index 81565bd41..4e7ad38cf 100644
--- a/docs/automation/webhook.md
+++ b/docs/automation/webhook.md
@@ -98,9 +98,41 @@ Mapping options (summary):
   (`channel` defaults to `last` and falls back to WhatsApp).
 - `allowUnsafeExternalContent: true` disables the external content safety wrapper for that hook
   (dangerous; only for trusted internal sources).
+- `cleanup: "delete"` automatically deletes the session and transcript after the hook completes.
+  Use `cleanupDelayMinutes` to delay cleanup for debugging or auditing.
 - `moltbot webhooks gmail setup` writes `hooks.gmail` config for `moltbot webhooks gmail run`.
 See [Gmail Pub/Sub](/automation/gmail-pubsub) for the full Gmail watch flow.
 
+### Session Cleanup
+
+By default, webhook hook sessions persist indefinitely. For fire-and-forget webhooks where session history has no value after completion, use the `cleanup` option:
+
+```json
+{
+  "hooks": {
+    "mappings": [{
+      "match": { "path": "gmail" },
+      "action": "agent",
+      "sessionKey": "hook:gmail:{{messages[0].id}}",
+      "cleanup": "delete",
+      "cleanupDelayMinutes": 5
+    }]
+  }
+}
+```
+
+| Option | Type | Default | Description |
+|--------|------|---------|-------------|
+| `cleanup` | `"delete"` \| `"keep"` | `"keep"` | Whether to delete session + transcript after completion |
+| `cleanupDelayMinutes` | `number` | `0` | Minutes to wait before cleanup (allows debugging/auditing) |
+
+When `cleanup: "delete"` is set:
+- The session entry is removed from `sessions.json`
+- The transcript `.jsonl` file is deleted
+- Cleanup runs asynchronously via a sweeper (every 60 seconds)
+- If `cleanupDelayMinutes` is set, cleanup is delayed by that many minutes
+- Failed cleanups are automatically retried on the next sweep
+
 ## Responses
 
 - `200` for `/hooks/wake`
diff --git a/src/config/types.hooks.test.ts b/src/config/types.hooks.test.ts
new file mode 100644
index 000000000..2129ee979
--- /dev/null
+++ b/src/config/types.hooks.test.ts
@@ -0,0 +1,45 @@
+import { describe, expect, it } from "vitest";
+import type { HookMappingConfig } from "./types.hooks.js";
+
+describe("HookMappingConfig", () => {
+  it("accepts cleanup option with delete value", () => {
+    const config: HookMappingConfig = {
+      id: "test",
+      match: { path: "test" },
+      action: "agent",
+      cleanup: "delete",
+    };
+    expect(config.cleanup).toBe("delete");
+  });
+
+  it("accepts cleanup option with keep value", () => {
+    const config: HookMappingConfig = {
+      id: "test",
+      match: { path: "test" },
+      action: "agent",
+      cleanup: "keep",
+    };
+    expect(config.cleanup).toBe("keep");
+  });
+
+  it("accepts cleanupDelayMinutes option", () => {
+    const config: HookMappingConfig = {
+      id: "test",
+      match: { path: "test" },
+      action: "agent",
+      cleanup: "delete",
+      cleanupDelayMinutes: 5,
+    };
+    expect(config.cleanupDelayMinutes).toBe(5);
+  });
+
+  it("allows cleanup fields to be omitted", () => {
+    const config: HookMappingConfig = {
+      id: "test",
+      match: { path: "test" },
+      action: "agent",
+    };
+    expect(config.cleanup).toBeUndefined();
+    expect(config.cleanupDelayMinutes).toBeUndefined();
+  });
+});
diff --git a/src/config/types.hooks.ts b/src/config/types.hooks.ts
index 7ca74605a..f097d2216 100644
--- a/src/config/types.hooks.ts
+++ b/src/config/types.hooks.ts
@@ -36,6 +36,10 @@ export type HookMappingConfig = {
   thinking?: string;
   timeoutSeconds?: number;
   transform?: HookMappingTransform;
+  /** Session cleanup after hook completes. "delete" removes session + transcript. Default: "keep" */
+  cleanup?: "delete" | "keep";
+  /** Minutes to wait before cleanup when cleanup="delete". Default: 0 (immediate) */
+  cleanupDelayMinutes?: number;
 };
 
 export type HooksGmailTailscaleMode = "off" | "serve" | "funnel";
diff --git a/src/gateway/hook-run-registry.store.test.ts b/src/gateway/hook-run-registry.store.test.ts
new file mode 100644
index 000000000..388a07d11
--- /dev/null
+++ b/src/gateway/hook-run-registry.store.test.ts
@@ -0,0 +1,108 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+
+vi.mock("../config/paths.js", () => ({
+  STATE_DIR: "/mock/state",
+}));
+
+vi.mock("../infra/json-file.js", () => ({
+  loadJsonFile: vi.fn(),
+  saveJsonFile: vi.fn(),
+}));
+
+describe("hook-run-registry.store", () => {
+  beforeEach(() => {
+    vi.resetModules();
+  });
+
+  afterEach(() => {
+    vi.resetAllMocks();
+  });
+
+  describe("loadHookRunRegistryFromDisk", () => {
+    it("returns empty map when file does not exist", async () => {
+      const { loadJsonFile } = await import("../infra/json-file.js");
+      vi.mocked(loadJsonFile).mockReturnValue(null);
+
+      const { loadHookRunRegistryFromDisk } = await import("./hook-run-registry.store.js");
+      const result = loadHookRunRegistryFromDisk();
+
+      expect(result.size).toBe(0);
+    });
+
+    it("loads and parses existing registry file", async () => {
+      const { loadJsonFile } = await import("../infra/json-file.js");
+      vi.mocked(loadJsonFile).mockReturnValue({
+        version: 1,
+        runs: {
+          "run-1": {
+            runId: "run-1",
+            sessionKey: "hook:test:1",
+            jobName: "test",
+            cleanup: "delete",
+            cleanupDelayMinutes: 0,
+            createdAt: 1000,
+          },
+        },
+      });
+
+      const { loadHookRunRegistryFromDisk } = await import("./hook-run-registry.store.js");
+      const result = loadHookRunRegistryFromDisk();
+
+      expect(result.size).toBe(1);
+      expect(result.get("run-1")?.sessionKey).toBe("hook:test:1");
+    });
+
+    it("returns empty map for invalid version", async () => {
+      const { loadJsonFile } = await import("../infra/json-file.js");
+      vi.mocked(loadJsonFile).mockReturnValue({
+        version: 999,
+        runs: { "run-1": { runId: "run-1" } },
+      });
+
+      const { loadHookRunRegistryFromDisk } = await import("./hook-run-registry.store.js");
+      const result = loadHookRunRegistryFromDisk();
+
+      expect(result.size).toBe(0);
+    });
+  });
+
+  describe("saveHookRunRegistryToDisk", () => {
+    it("writes versioned registry to disk", async () => {
+      const { saveJsonFile } = await import("../infra/json-file.js");
+      const mockSave = vi.mocked(saveJsonFile);
+
+      const { saveHookRunRegistryToDisk } = await import("./hook-run-registry.store.js");
+      const registry = new Map([
+        [
+          "run-1",
+          {
+            runId: "run-1",
+            sessionKey: "hook:test:1",
+            jobName: "test",
+            cleanup: "delete" as const,
+            cleanupDelayMinutes: 0,
+            createdAt: Date.now(),
+          },
+        ],
+      ]);
+
+      saveHookRunRegistryToDisk(registry);
+
+      expect(mockSave).toHaveBeenCalledWith(
+        expect.stringContaining("hook-runs.json"),
+        expect.objectContaining({ version: 1 }),
+      );
+    });
+  });
+
+  describe("resolveHookRunRegistryPath", () => {
+    it("returns path under STATE_DIR", async () => {
+      const { resolveHookRunRegistryPath } = await import("./hook-run-registry.store.js");
+      const result = resolveHookRunRegistryPath();
+
+      // Use path.sep-agnostic check for cross-platform compatibility
+      expect(result).toMatch(/mock[\\/]state/);
+      expect(result).toContain("hook-runs.json");
+    });
+  });
+});
diff --git a/src/gateway/hook-run-registry.store.ts b/src/gateway/hook-run-registry.store.ts
new file mode 100644
index 000000000..3eeffe1e0
--- /dev/null
+++ b/src/gateway/hook-run-registry.store.ts
@@ -0,0 +1,58 @@
+import path from "node:path";
+
+import { STATE_DIR } from "../config/paths.js";
+import { loadJsonFile, saveJsonFile } from "../infra/json-file.js";
+
+export type HookRunRecord = {
+  runId: string;
+  sessionKey: string;
+  jobName: string;
+  cleanup: "delete" | "keep";
+  cleanupDelayMinutes: number;
+  createdAt: number;
+  endedAt?: number;
+  cleanupAtMs?: number;
+  cleanupHandled?: boolean;
+};
+
+type PersistedHookRunRegistry = {
+  version: 1;
+  runs: Record<string, HookRunRecord>;
+};
+
+const REGISTRY_VERSION = 1 as const;
+
+export function resolveHookRunRegistryPath(): string {
+  return path.join(STATE_DIR, "hooks", "hook-runs.json");
+}
+
+export function loadHookRunRegistryFromDisk(): Map<string, HookRunRecord> {
+  const pathname = resolveHookRunRegistryPath();
+  const raw = loadJsonFile(pathname);
+  if (!raw || typeof raw !== "object") return new Map();
+  const record = raw as Partial<PersistedHookRunRegistry>;
+  if (record.version !== 1) return new Map();
+  const runsRaw = record.runs;
+  if (!runsRaw || typeof runsRaw !== "object") return new Map();
+  const out = new Map<string, HookRunRecord>();
+  for (const [runId, entry] of Object.entries(runsRaw)) {
+    if (!entry || typeof entry !== "object") continue;
+    const typed = entry as HookRunRecord;
+    if (!typed.runId || typeof typed.runId !== "string") continue;
+    out.set(runId, typed);
+  }
+  return out;
+}
+
+export function saveHookRunRegistryToDisk(runs: Map<string, HookRunRecord>): void {
+  const pathname = resolveHookRunRegistryPath();
+  const serialized: Record<string, HookRunRecord> = {};
+  for (const [runId, entry] of runs.entries()) {
+    serialized[runId] = entry;
+  }
+  const out: PersistedHookRunRegistry = {
+    version: REGISTRY_VERSION,
+    runs: serialized,
+  };
+  saveJsonFile(pathname, out);
+}
diff --git a/src/gateway/hook-run-registry.test.ts b/src/gateway/hook-run-registry.test.ts
new file mode 100644
index 000000000..94bf79403
--- /dev/null
+++ b/src/gateway/hook-run-registry.test.ts
@@ -0,0 +1,161 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+
+vi.mock("./hook-run-registry.store.js", () => ({
+  loadHookRunRegistryFromDisk: vi.fn(() => new Map()),
+  saveHookRunRegistryToDisk: vi.fn(),
+}));
+
+vi.mock("./call.js", () => ({
+  callGateway: vi.fn(),
+}));
+
+describe("hook-run-registry", () => {
+  beforeEach(() => {
+    vi.resetModules();
+    vi.useFakeTimers();
+  });
+
+  afterEach(() => {
+    vi.useRealTimers();
+    vi.resetAllMocks();
+  });
+
+  describe("registerHookRun", () => {
+    it("registers a new hook run with cleanup=delete", async () => {
+      const { registerHookRun, getHookRun, clearHookRuns } = await import("./hook-run-registry.js");
+      clearHookRuns();
+
+      registerHookRun({
+        runId: "run-1",
+        sessionKey: "hook:test:1",
+        jobName: "Test Hook",
+        cleanup: "delete",
+        cleanupDelayMinutes: 0,
+      });
+
+      const run = getHookRun("run-1");
+      expect(run).toBeDefined();
+      expect(run?.sessionKey).toBe("hook:test:1");
+      expect(run?.cleanup).toBe("delete");
+      expect(run?.cleanupHandled).toBe(false);
+
+      clearHookRuns();
+    });
+
+    it("does not register runs with cleanup=keep", async () => {
+      const { registerHookRun, getHookRun, clearHookRuns } = await import("./hook-run-registry.js");
+      clearHookRuns();
+
+      registerHookRun({
+        runId: "run-1",
+        sessionKey: "hook:test:1",
+        jobName: "Test Hook",
+        cleanup: "keep",
+        cleanupDelayMinutes: 0,
+      });
+
+      const run = getHookRun("run-1");
+      expect(run).toBeUndefined();
+
+      clearHookRuns();
+    });
+
+    it("does not register runs with cleanup=undefined", async () => {
+      const { registerHookRun, getHookRun, clearHookRuns } = await import("./hook-run-registry.js");
+      clearHookRuns();
+
+      registerHookRun({
+        runId: "run-1",
+        sessionKey: "hook:test:1",
+        jobName: "Test Hook",
+        cleanup: undefined,
+        cleanupDelayMinutes: undefined,
+      });
+
+      const run = getHookRun("run-1");
+      expect(run).toBeUndefined();
+
+      clearHookRuns();
+    });
+  });
+
+  describe("markHookRunComplete", () => {
+    it("sets endedAt, cleanupAtMs, and cleanupHandled", async () => {
+      const { registerHookRun, markHookRunComplete, getHookRun, clearHookRuns } =
+        await import("./hook-run-registry.js");
+      clearHookRuns();
+
+      registerHookRun({
+        runId: "run-1",
+        sessionKey: "hook:test:1",
+        jobName: "Test Hook",
+        cleanup: "delete",
+        cleanupDelayMinutes: 5,
+      });
+
+      const now = Date.now();
+      vi.setSystemTime(now);
+      markHookRunComplete("run-1");
+
+      const run = getHookRun("run-1");
+      expect(run?.endedAt).toBe(now);
+      expect(run?.cleanupAtMs).toBe(now + 5 * 60 * 1000);
+      expect(run?.cleanupHandled).toBe(true);
+
+      clearHookRuns();
+    });
+
+    it("handles immediate cleanup (cleanupDelayMinutes=0)", async () => {
+      const { registerHookRun, markHookRunComplete, getHookRun, clearHookRuns } =
+        await import("./hook-run-registry.js");
+      clearHookRuns();
+
+      registerHookRun({
+        runId: "run-1",
+        sessionKey: "hook:test:1",
+        jobName: "Test Hook",
+        cleanup: "delete",
+        cleanupDelayMinutes: 0,
+      });
+
+      const now = Date.now();
+      vi.setSystemTime(now);
+      markHookRunComplete("run-1");
+
+      const run = getHookRun("run-1");
+      expect(run?.cleanupAtMs).toBe(now);
+
+      clearHookRuns();
+    });
+  });
+
+  describe("initHookRunRegistry", () => {
+    it("restores runs from disk on init", async () => {
+      const { loadHookRunRegistryFromDisk } = await import("./hook-run-registry.store.js");
+      const existingRun = {
+        runId: "restored-run",
+        sessionKey: "hook:restored:1",
+        jobName: "Restored",
+        cleanup: "delete" as const,
+        cleanupDelayMinutes: 0,
+        createdAt: Date.now(),
+        cleanupHandled: true,
+        cleanupAtMs: Date.now(),
+      };
+      vi.mocked(loadHookRunRegistryFromDisk).mockReturnValue(
+        new Map([["restored-run", existingRun]]),
+      );
+
+      const { initHookRunRegistry, getHookRun, clearHookRuns } =
+        await import("./hook-run-registry.js");
+      clearHookRuns();
+      initHookRunRegistry();
+
+      const run = getHookRun("restored-run");
+      expect(run).toBeDefined();
+      expect(run?.sessionKey).toBe("hook:restored:1");
+
+      clearHookRuns();
+    });
+  });
+});
diff --git a/src/gateway/hook-run-registry.ts b/src/gateway/hook-run-registry.ts
new file mode 100644
index 000000000..6264e5ad8
--- /dev/null
+++ b/src/gateway/hook-run-registry.ts
@@ -0,0 +1,127 @@
+import { callGateway } from "./call.js";
+import {
+  type HookRunRecord,
+  loadHookRunRegistryFromDisk,
+  saveHookRunRegistryToDisk,
+} from "./hook-run-registry.store.js";
+
+const hookRuns = new Map<string, HookRunRecord>();
+let sweeper: NodeJS.Timeout | null = null;
+let restoreAttempted = false;
+
+function persistHookRuns() {
+  try {
+    saveHookRunRegistryToDisk(hookRuns);
+  } catch {
+    // Ignore persistence failures
+  }
+}
+
+function restoreHookRunsOnce() {
+  if (restoreAttempted) return;
+  restoreAttempted = true;
+  try {
+    const restored = loadHookRunRegistryFromDisk();
+    for (const [runId, entry] of restored.entries()) {
+      if (!hookRuns.has(runId)) {
+        hookRuns.set(runId, entry);
+      }
+    }
+    if (hookRuns.size > 0) startSweeper();
+  } catch {
+    // Ignore restore failures
+  }
+}
+
+function startSweeper() {
+  if (sweeper) return;
+  sweeper = setInterval(() => {
+    void sweepHookRuns();
+  }, 60_000);
+  sweeper.unref?.();
+}
+
+function stopSweeper() {
+  if (!sweeper) return;
+  clearInterval(sweeper);
+  sweeper = null;
+}
+
+async function sweepHookRuns() {
+  const now = Date.now();
+  let mutated = false;
+  for (const [runId, entry] of hookRuns.entries()) {
+    // Skip if not ready for cleanup
+    if (!entry.cleanupAtMs || entry.cleanupAtMs > now) continue;
+    // Skip if cleanup not yet marked (endedAt hasn't been set)
+    if (!entry.cleanupHandled) continue;
+
+    try {
+      await callGateway({
+        method: "sessions.delete",
+        params: { key: entry.sessionKey, deleteTranscript: true },
+        timeoutMs: 10_000,
+      });
+      // Only delete from registry after successful RPC
+      hookRuns.delete(runId);
+      mutated = true;
+    } catch {
+      // Log and retry on next sweep (entry stays in registry)
+    }
+  }
+  if (mutated) persistHookRuns();
+  if (hookRuns.size === 0) stopSweeper();
+}
+
+export function registerHookRun(params: {
+  runId: string;
+  sessionKey: string;
+  jobName: string;
+  cleanup: "delete" | "keep" | undefined;
+  cleanupDelayMinutes: number | undefined;
+}) {
+  restoreHookRunsOnce();
+
+  // Only track runs that need cleanup
+  if (params.cleanup !== "delete") return;
+
+  const now = Date.now();
+  hookRuns.set(params.runId, {
+    runId: params.runId,
+    sessionKey: params.sessionKey,
+    jobName: params.jobName,
+    cleanup: "delete",
+    cleanupDelayMinutes: params.cleanupDelayMinutes ?? 0,
+    createdAt: now,
+    cleanupHandled: false,
+  });
+  persistHookRuns();
+  startSweeper();
+}
+
+export function markHookRunComplete(runId: string) {
+  const entry = hookRuns.get(runId);
+  if (!entry) return;
+
+  const now = Date.now();
+  entry.endedAt = now;
+  entry.cleanupAtMs = now + entry.cleanupDelayMinutes * 60 * 1000;
+  entry.cleanupHandled = true;
+  persistHookRuns();
+}
+
+export function getHookRun(runId: string): HookRunRecord | undefined {
+  return hookRuns.get(runId);
+}
+
+/** Initialize registry on gateway startup - restores pending cleanups */
+export function initHookRunRegistry() {
+  restoreHookRunsOnce();
+}
+
+/** For testing only */
+export function clearHookRuns() {
+  hookRuns.clear();
+  stopSweeper();
+  restoreAttempted = false;
+}
diff --git a/src/gateway/hooks-cleanup.integration.test.ts b/src/gateway/hooks-cleanup.integration.test.ts
new file mode 100644
index 000000000..3a910e024
--- /dev/null
+++ b/src/gateway/hooks-cleanup.integration.test.ts
@@ -0,0 +1,173 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+
+vi.mock("./hook-run-registry.store.js", () => ({
+  loadHookRunRegistryFromDisk: vi.fn(() => new Map()),
+  saveHookRunRegistryToDisk: vi.fn(),
+}));
+
+vi.mock("./call.js", () => ({
+  callGateway: vi.fn().mockResolvedValue({ ok: true }),
+}));
+
+describe("webhook hook cleanup integration", () => {
+  beforeEach(() => {
+    vi.useFakeTimers();
+    vi.resetModules();
+  });
+
+  afterEach(() => {
+    vi.useRealTimers();
+    vi.resetAllMocks();
+  });
+
+  it("sweeper deletes session when cleanupAtMs is reached", async () => {
+    const { callGateway } = await import("./call.js");
+    const mockCallGateway = vi.mocked(callGateway);
+
+    const { registerHookRun, markHookRunComplete, clearHookRuns } =
+      await import("./hook-run-registry.js");
+    clearHookRuns();
+
+    // Register a hook run with immediate cleanup
+    registerHookRun({
+      runId: "test-run",
+      sessionKey: "hook:test:123",
+      jobName: "Test",
+      cleanup: "delete",
+      cleanupDelayMinutes: 0,
+    });
+
+    // Mark complete (sets cleanupAtMs to now and cleanupHandled to true)
+    markHookRunComplete("test-run");
+
+    // Advance time past the sweeper interval
+    await vi.advanceTimersByTimeAsync(61_000);
+
+    // Verify sessions.delete was called
+    expect(mockCallGateway).toHaveBeenCalledWith(
+      expect.objectContaining({
+        method: "sessions.delete",
+        params: { key: "hook:test:123", deleteTranscript: true },
+      }),
+    );
+
+    clearHookRuns();
+  });
+
+  it("does not delete session when cleanup=keep", async () => {
+    const { callGateway } = await import("./call.js");
+    const mockCallGateway = vi.mocked(callGateway);
+
+    const { registerHookRun, clearHookRuns } = await import("./hook-run-registry.js");
+    clearHookRuns();
+
+    // Register with cleanup=keep (should be no-op)
+    registerHookRun({
+      runId: "test-run",
+      sessionKey: "hook:test:123",
+      jobName: "Test",
+      cleanup: "keep",
+      cleanupDelayMinutes: 0,
+    });
+
+    // Advance time
+    await vi.advanceTimersByTimeAsync(120_000);
+
+    // Verify sessions.delete was NOT called
+    expect(mockCallGateway).not.toHaveBeenCalled();
+
+    clearHookRuns();
+  });
+
+  it("respects cleanupDelayMinutes", async () => {
+    const { callGateway } = await import("./call.js");
+    const mockCallGateway = vi.mocked(callGateway);
+
+    const { registerHookRun, markHookRunComplete, clearHookRuns } =
+      await import("./hook-run-registry.js");
+    clearHookRuns();
+
+    // Register with 5 minute delay
+    registerHookRun({
+      runId: "test-run",
+      sessionKey: "hook:test:123",
+      jobName: "Test",
+      cleanup: "delete",
+      cleanupDelayMinutes: 5,
+    });
+
+    markHookRunComplete("test-run");
+
+    // Advance 2 minutes - should NOT delete yet
+    await vi.advanceTimersByTimeAsync(2 * 60 * 1000);
+    expect(mockCallGateway).not.toHaveBeenCalled();
+
+    // Advance past 5 minutes total (need to trigger sweeper at 6 min mark)
+    await vi.advanceTimersByTimeAsync(4 * 60 * 1000);
+    expect(mockCallGateway).toHaveBeenCalledWith(
+      expect.objectContaining({
+        method: "sessions.delete",
+      }),
+    );
+
+    clearHookRuns();
+  });
+
+  it("retries on RPC failure", async () => {
+    const { callGateway } = await import("./call.js");
+    const mockCallGateway = vi.mocked(callGateway);
+    mockCallGateway.mockRejectedValueOnce(new Error("RPC failed"));
+    mockCallGateway.mockResolvedValueOnce({ ok: true });
+
+    const { registerHookRun, markHookRunComplete, getHookRun, clearHookRuns } =
+      await import("./hook-run-registry.js");
+    clearHookRuns();
+
+    registerHookRun({
+      runId: "test-run",
+      sessionKey: "hook:test:123",
+      jobName: "Test",
+      cleanup: "delete",
+      cleanupDelayMinutes: 0,
+    });
+
+    markHookRunComplete("test-run");
+
+    // First sweep - RPC fails, entry stays
+    await vi.advanceTimersByTimeAsync(61_000);
+    expect(mockCallGateway).toHaveBeenCalledTimes(1);
+    expect(getHookRun("test-run")).toBeDefined();
+
+    // Second sweep - RPC succeeds, entry removed
+    await vi.advanceTimersByTimeAsync(60_000);
+    expect(mockCallGateway).toHaveBeenCalledTimes(2);
+    expect(getHookRun("test-run")).toBeUndefined();
+
+    clearHookRuns();
+  });
+
+  it("does not delete session when cleanup=undefined", async () => {
+    const { callGateway } = await import("./call.js");
+    const mockCallGateway = vi.mocked(callGateway);
+
+    const { registerHookRun, clearHookRuns } = await import("./hook-run-registry.js");
+    clearHookRuns();
+
+    // Register with cleanup=undefined (should be no-op)
+    registerHookRun({
+      runId: "test-run",
+      sessionKey: "hook:test:123",
+      jobName: "Test",
+      cleanup: undefined,
+      cleanupDelayMinutes: undefined,
+    });
+
+    // Advance time
+    await vi.advanceTimersByTimeAsync(120_000);
+
+    // Verify sessions.delete was NOT called
+    expect(mockCallGateway).not.toHaveBeenCalled();
+
+    clearHookRuns();
+  });
+});
diff --git a/src/gateway/hooks-mapping.test.ts b/src/gateway/hooks-mapping.test.ts
index 8900ffd07..696d3ba51 100644
--- a/src/gateway/hooks-mapping.test.ts
+++ b/src/gateway/hooks-mapping.test.ts
@@ -3,6 +3,7 @@ import os from "node:os";
 import path from "node:path";
 import { describe, expect, it } from "vitest";
 
+import type { HookAction, HookMappingResolved } from "./hooks-mapping.js";
 import { applyHookMappings, resolveHookMappings } from "./hooks-mapping.js";
 
 const baseUrl = new URL("http://127.0.0.1:18789/hooks/gmail");
@@ -32,8 +33,7 @@ describe("hooks mapping", () => {
       path: "gmail",
     });
     expect(result?.ok).toBe(true);
-    if (result?.ok) {
-      expect(result.action.kind).toBe("agent");
+    if (result?.ok && result.action?.kind === "agent") {
       expect(result.action.message).toBe("Subject: Hello");
     }
   });
@@ -57,7 +57,7 @@ describe("hooks mapping", () => {
       path: "gmail",
     });
     expect(result?.ok).toBe(true);
-    if (result?.ok && result.action.kind === "agent") {
+    if (result?.ok && result.action?.kind === "agent") {
       expect(result.action.model).toBe("openai/gpt-4.1-mini");
     }
   });
@@ -90,11 +90,8 @@ describe("hooks mapping", () => {
     });
 
     expect(result?.ok).toBe(true);
-    if (result?.ok) {
-      expect(result.action.kind).toBe("wake");
-      if (result.action.kind === "wake") {
-        expect(result.action.text).toBe("Ping Ada");
-      }
+    if (result?.ok && result.action?.kind === "wake") {
+      expect(result.action.text).toBe("Ping Ada");
     }
   });
 
@@ -147,8 +144,7 @@ describe("hooks mapping", () => {
       path: "gmail",
     });
     expect(result?.ok).toBe(true);
-    if (result?.ok) {
-      expect(result.action.kind).toBe("agent");
+    if (result?.ok && result.action?.kind === "agent") {
       expect(result.action.message).toBe("Override subject: Hello");
     }
   });
@@ -166,3 +162,89 @@ describe("hooks mapping", () => {
     expect(result?.ok).toBe(false);
   });
 });
+
+describe("HookMappingResolved", () => {
+  it("includes cleanup fields", () => {
+    const resolved: HookMappingResolved = {
+      id: "test",
+      matchPath: "test",
+      action: "agent",
+      cleanup: "delete",
+      cleanupDelayMinutes: 5,
+    };
+    expect(resolved.cleanup).toBe("delete");
+    expect(resolved.cleanupDelayMinutes).toBe(5);
+  });
+});
+
+describe("HookAction", () => {
+  it("agent action includes cleanup fields", () => {
+    const action: HookAction = {
+      kind: "agent",
+      message: "test",
+      wakeMode: "now",
+      cleanup: "delete",
+      cleanupDelayMinutes: 5,
+    };
+    expect(action.kind).toBe("agent");
+    if (action.kind === "agent") {
+      expect(action.cleanup).toBe("delete");
+      expect(action.cleanupDelayMinutes).toBe(5);
+    }
+  });
+});
+
+describe("applyHookMappings cleanup propagation", () => {
+  it("propagates cleanup option from config to action", async () => {
+    const mappings = resolveHookMappings({
+      mappings: [
+        {
+          id: "test",
+          match: { path: "test" },
+          action: "agent",
+          messageTemplate: "hello",
+          cleanup: "delete",
+          cleanupDelayMinutes: 5,
+        },
+      ],
+    });
+
+    const result = await applyHookMappings(mappings, {
+      payload: {},
+      headers: {},
+      url: new URL("http://localhost/hooks/test"),
+      path: "test",
+    });
+
+    expect(result?.ok).toBe(true);
+    if (result?.ok && result.action?.kind === "agent") {
+      expect(result.action.cleanup).toBe("delete");
+      expect(result.action.cleanupDelayMinutes).toBe(5);
+    }
+  });
+
+  it("defaults cleanup to undefined when not specified", async () => {
+    const mappings = resolveHookMappings({
+      mappings: [
+        {
+          id: "test",
+          match: { path: "test" },
+          action: "agent",
+          messageTemplate: "hello",
+        },
+      ],
+    });
+
+    const result = await applyHookMappings(mappings, {
+      payload: {},
+      headers: {},
+      url: new URL("http://localhost/hooks/test"),
+      path: "test",
+    });
+
+    expect(result?.ok).toBe(true);
+    if (result?.ok && result.action?.kind === "agent") {
+      expect(result.action.cleanup).toBeUndefined();
+    }
+  });
+});
diff --git a/src/gateway/hooks-mapping.ts b/src/gateway/hooks-mapping.ts
index 2ebf9b136..9b4538380 100644
--- a/src/gateway/hooks-mapping.ts
+++ b/src/gateway/hooks-mapping.ts
@@ -21,6 +21,8 @@ export type HookMappingResolved = {
   model?: string;
   thinking?: string;
   timeoutSeconds?: number;
+  cleanup?: "delete" | "keep";
+  cleanupDelayMinutes?: number;
   transform?: HookMappingTransformResolved;
 };
 
@@ -55,6 +57,8 @@ export type HookAction =
       model?: string;
       thinking?: string;
       timeoutSeconds?: number;
+      cleanup?: "delete" | "keep";
+      cleanupDelayMinutes?: number;
     };
 
 export type HookMappingResult =
@@ -94,6 +98,8 @@ type HookTransformResult = Partial<{
   model: string;
   thinking: string;
   timeoutSeconds: number;
+  cleanup: "delete" | "keep";
+  cleanupDelayMinutes: number;
 }> | null;
 
 type HookTransformFn = (
@@ -191,6 +197,8 @@ function normalizeHookMapping(
     model: mapping.model,
     thinking: mapping.thinking,
     timeoutSeconds: mapping.timeoutSeconds,
+    cleanup: mapping.cleanup,
+    cleanupDelayMinutes: mapping.cleanupDelayMinutes,
     transform,
   };
 }
@@ -237,6 +245,8 @@ function buildActionFromMapping(
       model: renderOptional(mapping.model, ctx),
       thinking: renderOptional(mapping.thinking, ctx),
       timeoutSeconds: mapping.timeoutSeconds,
+      cleanup: mapping.cleanup,
+      cleanupDelayMinutes: mapping.cleanupDelayMinutes,
     },
   };
 }
@@ -277,6 +287,8 @@ function mergeAction(
     model: override.model ?? baseAgent?.model,
     thinking: override.thinking ?? baseAgent?.thinking,
     timeoutSeconds: override.timeoutSeconds ?? baseAgent?.timeoutSeconds,
+    cleanup: override.cleanup ?? baseAgent?.cleanup,
+    cleanupDelayMinutes: override.cleanupDelayMinutes ?? baseAgent?.cleanupDelayMinutes,
   });
 }
 
diff --git a/src/gateway/server-http.ts b/src/gateway/server-http.ts
index f08dc811c..07d8a3f02 100644
--- a/src/gateway/server-http.ts
+++ b/src/gateway/server-http.ts
@@ -47,6 +47,8 @@ type HookDispatchers = {
     thinking?: string;
     timeoutSeconds?: number;
     allowUnsafeExternalContent?: boolean;
+    cleanup?: "delete" | "keep";
+    cleanupDelayMinutes?: number;
   }) => string;
 };
 
@@ -182,6 +184,8 @@ export function createHooksRequestHandler(
             thinking: mapped.action.thinking,
             timeoutSeconds: mapped.action.timeoutSeconds,
             allowUnsafeExternalContent: mapped.action.allowUnsafeExternalContent,
+            cleanup: mapped.action.cleanup,
+            cleanupDelayMinutes: mapped.action.cleanupDelayMinutes,
           });
           sendJson(res, 202, { ok: true, runId });
           return true;
diff --git a/src/gateway/server.impl.ts b/src/gateway/server.impl.ts
index f641c4076..30cc22590 100644
--- a/src/gateway/server.impl.ts
+++ b/src/gateway/server.impl.ts
@@ -1,6 +1,7 @@
 import { resolveAgentWorkspaceDir, resolveDefaultAgentId } from "../agents/agent-scope.js";
 import { initSubagentRegistry } from "../agents/subagent-registry.js";
 import { registerSkillsChangeListener } from "../agents/skills/refresh.js";
+import { initHookRunRegistry } from "./hook-run-registry.js";
 import type { CanvasHostServer } from "../canvas-host/server.js";
 import { type ChannelId, listChannelPlugins } from "../channels/plugins/index.js";
 import { createDefaultDeps } from "../cli/deps.js";
@@ -216,6 +217,7 @@ export async function startGatewayServer(
   }
   setGatewaySigusr1RestartPolicy({ allowExternal: cfgAtStart.commands?.restart === true });
   initSubagentRegistry();
+  initHookRunRegistry();
   const defaultAgentId = resolveDefaultAgentId(cfgAtStart);
   const defaultWorkspaceDir = resolveAgentWorkspaceDir(cfgAtStart, defaultAgentId);
   const baseMethods = listGatewayMethods();
diff --git a/src/gateway/server/hooks.ts b/src/gateway/server/hooks.ts
index 18d46368f..382a36b67 100644
--- a/src/gateway/server/hooks.ts
+++ b/src/gateway/server/hooks.ts
@@ -9,6 +9,7 @@ import { requestHeartbeatNow } from "../../infra/heartbeat-wake.js";
 import { enqueueSystemEvent } from "../../infra/system-events.js";
 import type { createSubsystemLogger } from "../../logging/subsystem.js";
 import type { HookMessageChannel, HooksConfigResolved } from "../hooks.js";
+import { markHookRunComplete, registerHookRun } from "../hook-run-registry.js";
 import { createHooksRequestHandler } from "../server-http.js";
 
 type SubsystemLogger = ReturnType<typeof createSubsystemLogger>;
@@ -42,6 +43,8 @@ export function createGatewayHooksRequestHandler(params: {
     thinking?: string;
     timeoutSeconds?: number;
     allowUnsafeExternalContent?: boolean;
+    cleanup?: "delete" | "keep";
+    cleanupDelayMinutes?: number;
   }) => {
     const sessionKey = value.sessionKey.trim() ? value.sessionKey.trim() : `hook:${randomUUID()}`;
     const mainSessionKey = resolveMainSessionKeyFromConfig();
@@ -71,6 +74,13 @@ export function createGatewayHooksRequestHandler(params: {
     };
 
     const runId = randomUUID();
+    registerHookRun({
+      runId,
+      sessionKey,
+      jobName: value.name,
+      cleanup: value.cleanup,
+      cleanupDelayMinutes: value.cleanupDelayMinutes,
+    });
     void (async () => {
       try {
         const cfg = loadConfig();
@@ -88,10 +98,12 @@ export function createGatewayHooksRequestHandler(params: {
         enqueueSystemEvent(`${prefix}: ${summary}`.trim(), {
           sessionKey: mainSessionKey,
         });
+        markHookRunComplete(runId);
         if (value.wakeMode === "now") {
           requestHeartbeatNow({ reason: `hook:${jobId}` });
         }
       } catch (err) {
+        markHookRunComplete(runId);
         logHooks.warn(`hook agent failed: ${String(err)}`);
         enqueueSystemEvent(`Hook ${value.name} (error): ${String(err)}`, {
           sessionKey: mainSessionKey,