diff --git a/CHANGELOG.md b/CHANGELOG.md
index bf2e3358822..3a6ef1f9da4 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -20,6 +20,7 @@ Docs: https://docs.openclaw.ai
 - Providers/OpenRouter: stop adding empty DeepSeek V4 `reasoning_content` placeholders to assistant tool-call replay messages and strip empty replay artifacts before follow-up Chat Completions requests, so `openrouter/deepseek/deepseek-v4-pro` no longer fails after tool use. Fixes #82150. (#82158) Thanks @luyao618 and @Suquir0.
 - Gateway/approvals: treat `turnSourceTo` as optional in `canBridgeNoDeviceChatApprovalFromBackend`, matching the existing optional handling of `turnSourceAccountId` and `turnSourceThreadId`. Channels without a recipient concept (webchat, control-ui) leave `turnSourceTo` null on both the approval snapshot and the replay params, so the prior required-string check rejected every backend replay with `APPROVAL_CLIENT_MISMATCH`. Cross-channel replay is still gated by the required `turnSourceChannel` and `sessionKey` checks. Fixes #82132. (#82136) Thanks @ottodeng.
 - Cron: load runtime plugins before isolated cron model and delivery resolution so external channels can be selected for scheduled runs. (#82111) Thanks @medns.
+- Cron: preserve rotated transcript identity after session-bound scheduled runs compact, so `sessionTarget: "current"` keeps the next user message on the same conversation. Fixes #82164. Thanks @weissfl.
 - Twitch: keep gateway accounts running until shutdown instead of treating successful monitor startup as a clean channel exit, preventing immediate auto-restart loops. Fixes #60071. (#81853) Thanks @edenfunf.
 - Agents/auto-reply: honor `agents.defaults.silentReply` and per-surface group silent-reply policy when generic agent-run failure fallbacks decide whether to send visible fallback text. Fixes #82060. (#82086) Thanks @taozengabc.
 - Discord: render channel topic context as structured untrusted metadata in reply prompts and stop duplicating inbound message bodies or exposing raw `EXTERNAL_UNTRUSTED_CONTENT` envelopes. Fixes #82168. Thanks @ronan-dandelion-cult.
diff --git a/src/agents/pi-embedded-runner/run.ts b/src/agents/pi-embedded-runner/run.ts
index de33df550d5..abdafabb5e9 100644
--- a/src/agents/pi-embedded-runner/run.ts
+++ b/src/agents/pi-embedded-runner/run.ts
@@ -1169,6 +1169,7 @@ export async function runEmbeddedPiAgent(
               durationMs: Date.now() - started,
               agentMeta: buildErrorAgentMeta({
                 sessionId: activeSessionId,
+                sessionFile: activeSessionFile,
                 provider,
                 model: model.id,
                 contextTokens: ctxInfo.tokens,
@@ -1465,6 +1466,7 @@ export async function runEmbeddedPiAgent(
               durationMs: Date.now() - started,
               agentMeta: buildErrorAgentMeta({
                 sessionId: activeSessionId,
+                sessionFile: activeSessionFile,
                 provider,
                 model: model.id,
                 contextTokens: ctxInfo.tokens,
@@ -1967,6 +1969,7 @@ export async function runEmbeddedPiAgent(
                 durationMs: Date.now() - started,
                 agentMeta: buildErrorAgentMeta({
                   sessionId: sessionIdUsed,
+                  sessionFile: activeSessionFile,
                   provider,
                   model: model.id,
                   contextTokens: ctxInfo.tokens,
@@ -1997,6 +2000,7 @@ export async function runEmbeddedPiAgent(
                 durationMs: Date.now() - started,
                 agentMeta: buildErrorAgentMeta({
                   sessionId: sessionIdUsed,
+                  sessionFile: activeSessionFile,
                   provider,
                   model: model.id,
                   contextTokens: ctxInfo.tokens,
@@ -2068,6 +2072,7 @@ export async function runEmbeddedPiAgent(
                   durationMs: Date.now() - started,
                   agentMeta: buildErrorAgentMeta({
                     sessionId: sessionIdUsed,
+                    sessionFile: activeSessionFile,
                     provider,
                     model: model.id,
                     contextTokens: ctxInfo.tokens,
@@ -2108,6 +2113,7 @@ export async function runEmbeddedPiAgent(
                   durationMs: Date.now() - started,
                   agentMeta: buildErrorAgentMeta({
                     sessionId: sessionIdUsed,
+                    sessionFile: activeSessionFile,
                     provider,
                     model: model.id,
                     contextTokens: ctxInfo.tokens,
diff --git a/src/agents/pi-embedded-runner/run/helpers.test.ts b/src/agents/pi-embedded-runner/run/helpers.test.ts
index 19872908427..3ea2be102d8 100644
--- a/src/agents/pi-embedded-runner/run/helpers.test.ts
+++ b/src/agents/pi-embedded-runner/run/helpers.test.ts
@@ -1,6 +1,10 @@
 import type { AssistantMessage } from "@earendil-works/pi-ai";
 import { describe, expect, it } from "vitest";
-import { resolveFinalAssistantRawText, resolveFinalAssistantVisibleText } from "./helpers.js";
+import {
+  buildErrorAgentMeta,
+  resolveFinalAssistantRawText,
+  resolveFinalAssistantVisibleText,
+} from "./helpers.js";
 
 function makeAssistantMessage(
   content: AssistantMessage["content"],
@@ -73,3 +77,21 @@ describe("resolveFinalAssistantVisibleText", () => {
     expect(resolveFinalAssistantRawText(lastAssistant)).toBe("<final>keep this</final>");
   });
 });
+
+describe("buildErrorAgentMeta", () => {
+  it("preserves active session file for error exits after transcript rotation", () => {
+    expect(
+      buildErrorAgentMeta({
+        sessionId: "session-rotated",
+        sessionFile: "/tmp/session-rotated.jsonl",
+        provider: "anthropic",
+        model: "claude-opus-4-6",
+        usageAccumulator: {},
+        lastRunPromptUsage: undefined,
+      }),
+    ).toMatchObject({
+      sessionId: "session-rotated",
+      sessionFile: "/tmp/session-rotated.jsonl",
+    });
+  });
+});
diff --git a/src/agents/pi-embedded-runner/run/helpers.ts b/src/agents/pi-embedded-runner/run/helpers.ts
index 72dd04730fb..21f21d70221 100644
--- a/src/agents/pi-embedded-runner/run/helpers.ts
+++ b/src/agents/pi-embedded-runner/run/helpers.ts
@@ -161,6 +161,7 @@ export function buildUsageAgentMetaFields(params: {
  */
 export function buildErrorAgentMeta(params: {
   sessionId: string;
+  sessionFile?: string;
   provider: string;
   model: string;
   contextTokens?: number;
@@ -177,6 +178,7 @@ export function buildErrorAgentMeta(params: {
   });
   return {
     sessionId: params.sessionId,
+    ...(params.sessionFile ? { sessionFile: params.sessionFile } : {}),
     provider: params.provider,
     model: params.model,
     ...(params.contextTokens ? { contextTokens: params.contextTokens } : {}),
diff --git a/src/cron/isolated-agent.session-identity.test.ts b/src/cron/isolated-agent.session-identity.test.ts
index b7d4d670b8d..508eacb2bf7 100644
--- a/src/cron/isolated-agent.session-identity.test.ts
+++ b/src/cron/isolated-agent.session-identity.test.ts
@@ -4,7 +4,12 @@ import path from "node:path";
 import { beforeEach, describe, expect, it, vi } from "vitest";
 import * as modelThinkingDefault from "../agents/model-thinking-default.js";
 import { runCronIsolatedAgentTurn } from "./isolated-agent.js";
-import { makeCfg, makeJob, writeSessionStore } from "./isolated-agent.test-harness.js";
+import {
+  makeCfg,
+  makeJob,
+  writeSessionStore,
+  writeSessionStoreEntries,
+} from "./isolated-agent.test-harness.js";
 import {
   DEFAULT_AGENT_TURN_PAYLOAD,
   DEFAULT_MESSAGE,
@@ -18,6 +23,7 @@ import { setupRunCronIsolatedAgentTurnSuite } from "./isolated-agent/run.suite-h
 import {
   mockRunCronFallbackPassthrough,
   runEmbeddedPiAgentMock,
+  updateSessionStoreMock,
 } from "./isolated-agent/run.test-harness.js";
 
 setupRunCronIsolatedAgentTurnSuite();
@@ -142,6 +148,79 @@ describe("runCronIsolatedAgentTurn session identity", () => {
     });
   });
 
+  it("persists rotated transcript identity for session-bound cron runs", async () => {
+    await withTempHome(async (home) => {
+      const deps = makeDeps();
+      const boundSessionKey = "agent:main:telegram:direct:42";
+      const originalSessionFile = path.join(home, "bound-session.jsonl");
+      const rotatedSessionFile = path.join(home, "bound-session-rotated.jsonl");
+      const storePath = await writeSessionStoreEntries(home, {
+        [boundSessionKey]: {
+          sessionId: "bound-session",
+          sessionFile: originalSessionFile,
+          updatedAt: Date.now(),
+          lastInteractionAt: Date.now() - 1_000,
+          systemSent: true,
+        },
+      });
+      runEmbeddedPiAgentMock.mockResolvedValueOnce({
+        payloads: [{ text: "ok" }],
+        meta: {
+          durationMs: 5,
+          agentMeta: {
+            sessionId: "bound-session-rotated",
+            sessionFile: rotatedSessionFile,
+            provider: "anthropic",
+            model: "claude-opus-4-6",
+            compactionCount: 1,
+            compactionTokensAfter: 42,
+          },
+        },
+      });
+      updateSessionStoreMock.mockImplementation(async (_storePath, update) => {
+        const store = {
+          [boundSessionKey]: {
+            sessionId: "bound-session",
+            sessionFile: originalSessionFile,
+            updatedAt: Date.now(),
+            lastInteractionAt: Date.now() - 1_000,
+            systemSent: true,
+          },
+        };
+        update(store);
+      });
+
+      const res = await runCronIsolatedAgentTurn({
+        cfg: makeCfg(home, storePath),
+        deps,
+        job: {
+          ...makeJob(DEFAULT_AGENT_TURN_PAYLOAD),
+          sessionTarget: `session:${boundSessionKey}`,
+          delivery: { mode: "none" },
+        },
+        message: DEFAULT_MESSAGE,
+        sessionKey: boundSessionKey,
+        lane: "cron",
+      });
+
+      expect(res.status).toBe("ok");
+      expect(res.sessionId).toBe("bound-session-rotated");
+
+      const finalPersist = updateSessionStoreMock.mock.calls.at(-1);
+      expect(finalPersist?.[0]).toBe(storePath);
+      const persistedStore: Record<string, { [key: string]: unknown }> = {};
+      (finalPersist?.[1] as (store: typeof persistedStore) => void)(persistedStore);
+      expect(persistedStore[boundSessionKey]).toEqual(
+        expect.objectContaining({
+          sessionId: "bound-session-rotated",
+          sessionFile: rotatedSessionFile,
+          usageFamilyKey: boundSessionKey,
+          usageFamilySessionIds: ["bound-session", "bound-session-rotated"],
+        }),
+      );
+    });
+  });
+
   it("uses lightweight bootstrap context for command-style cron payloads", async () => {
     await withTempHome(async (home) => {
       await runCronTurn(home, {
diff --git a/src/cron/isolated-agent/run-session-state.test.ts b/src/cron/isolated-agent/run-session-state.test.ts
index d1bd7b0f666..738e62943b1 100644
--- a/src/cron/isolated-agent/run-session-state.test.ts
+++ b/src/cron/isolated-agent/run-session-state.test.ts
@@ -4,7 +4,11 @@ import os from "node:os";
 import path from "node:path";
 import { describe, expect, it, vi } from "vitest";
 import type { SessionEntry } from "../../config/sessions.js";
-import { createPersistCronSessionEntry, type MutableCronSession } from "./run-session-state.js";
+import {
+  adoptCronRunSessionMetadata,
+  createPersistCronSessionEntry,
+  type MutableCronSession,
+} from "./run-session-state.js";
 
 function makeSessionEntry(overrides?: Partial<SessionEntry>): SessionEntry {
   return {
@@ -159,6 +163,56 @@ describe("createPersistCronSessionEntry", () => {
 
     expect(cronSession.store["agent:main:session"]).toBe(cronSession.sessionEntry);
   });
+
+  it("adopts rotated run transcript metadata before persisting session-bound cron state", async () => {
+    const cronSession = makeCronSession(
+      makeSessionEntry({
+        sessionId: "bound-session",
+        sessionFile: "/tmp/bound-session.jsonl",
+      }),
+    );
+    const changed = adoptCronRunSessionMetadata({
+      entry: cronSession.sessionEntry,
+      sessionKey: "agent:main:telegram:direct:42",
+      runMeta: {
+        sessionId: "bound-session-rotated",
+        sessionFile: "/tmp/bound-session-rotated.jsonl",
+      },
+    });
+    const updateSessionStore = vi.fn(
+      async (_storePath, update: (store: Record<string, SessionEntry>) => void) => {
+        const store: Record<string, SessionEntry> = {};
+        update(store);
+        expect(store["agent:main:telegram:direct:42"]).toEqual({
+          sessionId: "bound-session-rotated",
+          sessionFile: "/tmp/bound-session-rotated.jsonl",
+          usageFamilyKey: "agent:main:telegram:direct:42",
+          usageFamilySessionIds: ["bound-session", "bound-session-rotated"],
+          updatedAt: 1000,
+          systemSent: true,
+        });
+      },
+    );
+
+    expect(changed).toBe(true);
+    const persist = createPersistCronSessionEntry({
+      isFastTestEnv: false,
+      cronSession,
+      agentSessionKey: "agent:main:telegram:direct:42",
+      updateSessionStore,
+    });
+
+    await persist();
+
+    expect(cronSession.store["agent:main:telegram:direct:42"]).toEqual({
+      sessionId: "bound-session-rotated",
+      sessionFile: "/tmp/bound-session-rotated.jsonl",
+      usageFamilyKey: "agent:main:telegram:direct:42",
+      usageFamilySessionIds: ["bound-session", "bound-session-rotated"],
+      updatedAt: 1000,
+      systemSent: true,
+    });
+  });
 });
 
 async function createTranscriptFile(): Promise<string> {
diff --git a/src/cron/isolated-agent/run-session-state.ts b/src/cron/isolated-agent/run-session-state.ts
index 337a1422ec6..a3c16abc1ed 100644
--- a/src/cron/isolated-agent/run-session-state.ts
+++ b/src/cron/isolated-agent/run-session-state.ts
@@ -26,6 +26,11 @@ function cronTranscriptExists(entry: SessionEntry): boolean {
   return Boolean(sessionFile && fs.existsSync(sessionFile));
 }
 
+function normalizeSessionField(value: string | undefined): string | undefined {
+  const trimmed = value?.trim();
+  return trimmed ? trimmed : undefined;
+}
+
 function toNonResumableCronSessionEntry(entry: SessionEntry): SessionEntry {
   const next = { ...entry } as Partial<SessionEntry>;
   delete next.sessionId;
@@ -61,6 +66,43 @@ export function createPersistCronSessionEntry(params: {
   };
 }
 
+export function adoptCronRunSessionMetadata(params: {
+  entry: MutableCronSessionEntry;
+  sessionKey: string;
+  runMeta?: {
+    sessionId?: string;
+    sessionFile?: string;
+  };
+}): boolean {
+  const nextSessionId = normalizeSessionField(params.runMeta?.sessionId);
+  const nextSessionFile = normalizeSessionField(params.runMeta?.sessionFile);
+  if (!nextSessionFile) {
+    return false;
+  }
+
+  let changed = false;
+  const previousSessionId = params.entry.sessionId;
+  if (nextSessionId && nextSessionId !== previousSessionId) {
+    params.entry.sessionId = nextSessionId;
+    params.entry.usageFamilyKey = params.entry.usageFamilyKey ?? params.sessionKey;
+    params.entry.usageFamilySessionIds = Array.from(
+      new Set([
+        ...(params.entry.usageFamilySessionIds ?? []),
+        ...(previousSessionId ? [previousSessionId] : []),
+        nextSessionId,
+      ]),
+    );
+    changed = true;
+  }
+
+  if (nextSessionFile !== params.entry.sessionFile) {
+    params.entry.sessionFile = nextSessionFile;
+    changed = true;
+  }
+
+  return changed;
+}
+
 export async function persistCronSkillsSnapshotIfChanged(params: {
   isFastTestEnv: boolean;
   cronSession: MutableCronSession;
diff --git a/src/cron/isolated-agent/run.ts b/src/cron/isolated-agent/run.ts
index b5e24fb81a7..ddf21fd8183 100644
--- a/src/cron/isolated-agent/run.ts
+++ b/src/cron/isolated-agent/run.ts
@@ -37,6 +37,7 @@ import {
 import { resolveCronModelSelection } from "./model-selection.js";
 import { buildCronAgentDefaultsConfig } from "./run-config.js";
 import {
+  adoptCronRunSessionMetadata,
   createPersistCronSessionEntry,
   markCronSessionPreRun,
   persistCronSkillsSnapshotIfChanged,
@@ -580,7 +581,7 @@ async function prepareCronRunContext(params: {
   });
   const withRunSession: WithRunSession = (result) => ({
     ...result,
-    sessionId: runSessionId,
+    sessionId: cronSession.sessionEntry.sessionId ?? runSessionId,
     sessionKey: runSessionKey,
   });
   if (!cronSession.sessionEntry.label?.trim() && baseSessionKey.startsWith("cron:")) {
@@ -852,6 +853,11 @@ async function finalizeCronRun(params: {
   if (finalRunResult.meta?.systemPromptReport) {
     prepared.cronSession.sessionEntry.systemPromptReport = finalRunResult.meta.systemPromptReport;
   }
+  adoptCronRunSessionMetadata({
+    entry: prepared.cronSession.sessionEntry,
+    sessionKey: prepared.agentSessionKey,
+    runMeta: finalRunResult.meta?.agentMeta,
+  });
   const usage = finalRunResult.meta?.agentMeta?.usage;
   const promptTokens = finalRunResult.meta?.agentMeta?.promptTokens;
   const modelUsed =