fix(gateway): invalidate bootstrap cache on session rollover (openclaw#38535)

Verified:
- pnpm install --frozen-lockfile
- pnpm build
- pnpm check
- pnpm test:macmini

Co-authored-by: yfge <1186273+yfge@users.noreply.github.com>
Co-authored-by: Tak Hoffman <781889+Takhoffman@users.noreply.github.com>

CHANGELOG.md

@@ -225,6 +225,7 @@ Docs: https://docs.openclaw.ai
 - ACP/console silent reply suppression: filter ACP `NO_REPLY` lead fragments and silent-only finals before `openclaw agent` logging/delivery so console-backed ACP sessions no longer leak `NO`/`NO_REPLY` placeholders. (#38436) Thanks @ql-wade.
 - Feishu/reply delivery reliability: disable block streaming in Feishu reply options so plain-text auto-render replies are no longer silently dropped before final delivery. (#38258) Thanks @xinhuagu.
 - Agents/reply MEDIA delivery: normalize local assistant `MEDIA:` paths before block/final delivery, keep media dedupe aligned with message-tool sends, and contain malformed media normalization failures so generated files send reliably instead of falling back to empty responses. (#38572) Thanks @obviyus.
+- Sessions/bootstrap cache rollover invalidation: clear cached workspace bootstrap snapshots whenever an existing `sessionKey` rolls to a new `sessionId` across auto-reply, command, and isolated cron session resolvers, so `AGENTS.md`/`MEMORY.md`/`USER.md` updates are reloaded after daily, idle, or forced session resets instead of staying stale until gateway restart. (#38494) Thanks @LivingInDrm.
 
 ## 2026.3.2
 

src/agents/bootstrap-cache.ts

@@ -20,6 +20,17 @@ export function clearBootstrapSnapshot(sessionKey: string): void {
   cache.delete(sessionKey);
 }
 
+export function clearBootstrapSnapshotOnSessionRollover(params: {
+  sessionKey?: string;
+  previousSessionId?: string;
+}): void {
+  if (!params.sessionKey || !params.previousSessionId) {
+    return;
+  }
+
+  clearBootstrapSnapshot(params.sessionKey);
+}
+
 export function clearAllBootstrapSnapshots(): void {
   cache.clear();
 }

src/auto-reply/reply/session.test.ts

@@ -2,6 +2,7 @@ import fs from "node:fs/promises";
 import os from "node:os";
 import path from "node:path";
 import { afterAll, afterEach, beforeAll, beforeEach, describe, expect, it, vi } from "vitest";
+import * as bootstrapCache from "../../agents/bootstrap-cache.js";
 import { buildModelAliasIndex } from "../../agents/model-selection.js";
 import type { OpenClawConfig } from "../../config/config.js";
 import type { SessionEntry } from "../../config/sessions.js";
@@ -850,11 +851,18 @@ describe("initSessionState RawBody", () => {
 });
 
 describe("initSessionState reset policy", () => {
+  let clearBootstrapSnapshotOnSessionRolloverSpy: ReturnType<typeof vi.spyOn>;
+
   beforeEach(() => {
     vi.useFakeTimers();
+    clearBootstrapSnapshotOnSessionRolloverSpy = vi.spyOn(
+      bootstrapCache,
+      "clearBootstrapSnapshotOnSessionRollover",
+    );
   });
 
   afterEach(() => {
+    clearBootstrapSnapshotOnSessionRolloverSpy.mockRestore();
     vi.useRealTimers();
   });
 
@@ -881,6 +889,10 @@ describe("initSessionState reset policy", () => {
 
     expect(result.isNewSession).toBe(true);
     expect(result.sessionId).not.toBe(existingSessionId);
+    expect(clearBootstrapSnapshotOnSessionRolloverSpy).toHaveBeenCalledWith({
+      sessionKey,
+      previousSessionId: existingSessionId,
+    });
   });
 
   it("treats sessions as stale before the daily reset when updated before yesterday's boundary", async () => {
@@ -1057,6 +1069,10 @@ describe("initSessionState reset policy", () => {
 
     expect(result.isNewSession).toBe(false);
     expect(result.sessionId).toBe(existingSessionId);
+    expect(clearBootstrapSnapshotOnSessionRolloverSpy).toHaveBeenCalledWith({
+      sessionKey,
+      previousSessionId: undefined,
+    });
   });
 });
 

src/auto-reply/reply/session.ts

@@ -5,6 +5,7 @@ import {
   parseTelegramChatIdFromTarget,
 } from "../../acp/conversation-id.js";
 import { resolveSessionAgentId } from "../../agents/agent-scope.js";
+import { clearBootstrapSnapshotOnSessionRollover } from "../../agents/bootstrap-cache.js";
 import { normalizeChatType } from "../../channels/chat-type.js";
 import type { OpenClawConfig } from "../../config/config.js";
 import {
@@ -358,6 +359,10 @@ export async function initSessionState(params: {
   // and for scheduled/daily resets where the session has become stale (!freshEntry).
   // Without this, daily-reset transcripts are left as orphaned files on disk (#35481).
   const previousSessionEntry = (resetTriggered || !freshEntry) && entry ? { ...entry } : undefined;
+  clearBootstrapSnapshotOnSessionRollover({
+    sessionKey,
+    previousSessionId: previousSessionEntry?.sessionId,
+  });
 
   if (!isNewSession && freshEntry) {
     sessionId = entry.sessionId;

src/commands/agent/session.ts

@@ -1,5 +1,6 @@
 import crypto from "node:crypto";
 import { listAgentIds } from "../../agents/agent-scope.js";
+import { clearBootstrapSnapshotOnSessionRollover } from "../../agents/bootstrap-cache.js";
 import type { MsgContext } from "../../auto-reply/templating.js";
 import {
   normalizeThinkLevel,
@@ -144,6 +145,11 @@ export function resolveSession(opts: {
     opts.sessionId?.trim() || (fresh ? sessionEntry?.sessionId : undefined) || crypto.randomUUID();
   const isNewSession = !fresh && !opts.sessionId;
 
+  clearBootstrapSnapshotOnSessionRollover({
+    sessionKey,
+    previousSessionId: isNewSession ? sessionEntry?.sessionId : undefined,
+  });
+
   const persistedThinking =
     fresh && sessionEntry?.thinkingLevel
       ? normalizeThinkLevel(sessionEntry.thinkingLevel)

src/cron/isolated-agent/session.test.ts

@@ -1,4 +1,4 @@
-import { describe, expect, it, vi } from "vitest";
+import { beforeEach, describe, expect, it, vi } from "vitest";
 import type { OpenClawConfig } from "../../config/config.js";
 
 vi.mock("../../config/sessions.js", () => ({
@@ -8,6 +8,16 @@ vi.mock("../../config/sessions.js", () => ({
   resolveSessionResetPolicy: vi.fn().mockReturnValue({ mode: "idle", idleMinutes: 60 }),
 }));
 
+vi.mock("../../agents/bootstrap-cache.js", () => ({
+  clearBootstrapSnapshot: vi.fn(),
+  clearBootstrapSnapshotOnSessionRollover: vi.fn(({ sessionKey, previousSessionId }) => {
+    if (sessionKey && previousSessionId) {
+      clearBootstrapSnapshot(sessionKey);
+    }
+  }),
+}));
+
+import { clearBootstrapSnapshot } from "../../agents/bootstrap-cache.js";
 import { loadSessionStore, evaluateSessionFreshness } from "../../config/sessions.js";
 import { resolveCronSession } from "./session.js";
 
@@ -40,6 +50,10 @@ function resolveWithStoredEntry(params?: {
 }
 
 describe("resolveCronSession", () => {
+  beforeEach(() => {
+    vi.mocked(clearBootstrapSnapshot).mockReset();
+  });
+
   it("preserves modelOverride and providerOverride from existing session entry", () => {
     const result = resolveWithStoredEntry({
       sessionKey: "agent:main:cron:test-job",
@@ -100,6 +114,7 @@ describe("resolveCronSession", () => {
       expect(result.sessionEntry.sessionId).toBe("existing-session-id-123");
       expect(result.isNewSession).toBe(false);
       expect(result.systemSent).toBe(true);
+      expect(clearBootstrapSnapshot).not.toHaveBeenCalled();
     });
 
     it("creates new sessionId when session is stale", () => {
@@ -121,6 +136,7 @@ describe("resolveCronSession", () => {
       expect(result.sessionEntry.modelOverride).toBe("gpt-4.1-mini");
       expect(result.sessionEntry.providerOverride).toBe("openai");
       expect(result.sessionEntry.sendPolicy).toBe("allow");
+      expect(clearBootstrapSnapshot).toHaveBeenCalledWith("webhook:stable-key");
     });
 
     it("creates new sessionId when forceNew is true", () => {
@@ -141,6 +157,7 @@ describe("resolveCronSession", () => {
       expect(result.systemSent).toBe(false);
       expect(result.sessionEntry.modelOverride).toBe("sonnet-4");
       expect(result.sessionEntry.providerOverride).toBe("anthropic");
+      expect(clearBootstrapSnapshot).toHaveBeenCalledWith("webhook:stable-key");
     });
 
     it("clears delivery routing metadata and deliveryContext when forceNew is true", () => {

src/cron/isolated-agent/session.ts

@@ -1,4 +1,5 @@
 import crypto from "node:crypto";
+import { clearBootstrapSnapshotOnSessionRollover } from "../../agents/bootstrap-cache.js";
 import type { OpenClawConfig } from "../../config/config.js";
 import {
   evaluateSessionFreshness,
@@ -58,6 +59,11 @@ export function resolveCronSession(params: {
     systemSent = false;
   }
 
+  clearBootstrapSnapshotOnSessionRollover({
+    sessionKey: params.sessionKey,
+    previousSessionId: isNewSession ? entry?.sessionId : undefined,
+  });
+
   const sessionEntry: SessionEntry = {
     // Preserve existing per-session overrides even when rolling to a new sessionId.
     ...entry,