diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2a380dbc08a..52b5958185e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -311,6 +311,7 @@ Docs: https://docs.openclaw.ai
 - Discord/gateway: count failed health-monitor restart attempts toward cooldown and hourly caps, and evict stale account lifecycle state during channel reloads so repeated Discord gateway recovery cannot loop on old status. Fixes #38596. (#40413) Thanks @jellyAI-dev and @vashquez.
 - TTS/BlueBubbles: pre-transcode synthesized MP3 audio to opus-in-CAF (mono, 24 kHz — validated against macOS 15.x Messages.app's native voice-memo CAF descriptor) on macOS hosts before handing the file to BlueBubbles, so iMessage renders the result as a native voice-memo bubble with proper duration and waveform UI instead of a plain file attachment. Adds an opt-in `tts.voice.preferAudioFileFormat` channel capability and a magic-byte sniff for the CAF container so the host-local-media validator (which uses `file-type` and didn't recognize CAF natively) can verify the pre-transcoded buffer. Channels that don't opt in are unaffected. (#72586) Fixes #72506. Thanks @omarshahine.
 - Feishu: retry WebSocket startup failures with monitor-owned backoff while preserving SDK-local heartbeat defaults, so persistent-connection startup failures no longer leave the monitor hung. Fixes #68766; related #42354 and #55532. Thanks @alex-xuweilong, @120106835, @sirfengyu, and @tianhaocui.
+- Auto-reply/session: carry the tail of user/assistant turns into the freshly-rotated transcript on silent in-reply session resets (compaction failure, role-ordering conflict) so direct-chat continuity survives the rebind. Fixes #70853. (#70898) Thanks @neeravmakwana.
 
 ## 2026.4.26
 
diff --git a/src/auto-reply/reply/agent-runner-session-reset.ts b/src/auto-reply/reply/agent-runner-session-reset.ts
index 3a7eaed9601..46cfc2efbee 100644
--- a/src/auto-reply/reply/agent-runner-session-reset.ts
+++ b/src/auto-reply/reply/agent-runner-session-reset.ts
@@ -10,6 +10,7 @@ import {
 import { generateSecureUuid } from "../../infra/secure-random.js";
 import { defaultRuntime } from "../../runtime.js";
 import { refreshQueuedFollowupSession, type FollowupRun } from "./queue.js";
+import { replayRecentUserAssistantMessages } from "./session-transcript-replay.js";
 
 type ResetSessionOptions = {
   failureLabel: string;
@@ -96,6 +97,13 @@ export async function resetReplyRunSession(params: {
       `Failed to persist session reset after ${params.options.failureLabel} (${params.sessionKey}): ${String(err)}`,
     );
   }
+  // Silent rotations (compaction/role-ordering) fire without user intent, so
+  // preserve recent user/assistant turns for direct-chat continuity.
+  replayRecentUserAssistantMessages({
+    sourceTranscript: prevEntry.sessionFile,
+    targetTranscript: nextSessionFile,
+    newSessionId: nextSessionId,
+  });
   params.followupRun.run.sessionId = nextSessionId;
   params.followupRun.run.sessionFile = nextSessionFile;
   deps.refreshQueuedFollowupSession({
diff --git a/src/auto-reply/reply/session-transcript-replay.test.ts b/src/auto-reply/reply/session-transcript-replay.test.ts
new file mode 100644
index 00000000000..20c754623dd
--- /dev/null
+++ b/src/auto-reply/reply/session-transcript-replay.test.ts
@@ -0,0 +1,51 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+import { afterEach, beforeEach, describe, expect, it } from "vitest";
+import {
+  DEFAULT_REPLAY_MAX_MESSAGES,
+  replayRecentUserAssistantMessages,
+} from "./session-transcript-replay.js";
+
+const j = (obj: unknown): string => `${JSON.stringify(obj)}\n`;
+
+describe("replayRecentUserAssistantMessages", () => {
+  let root = "";
+  beforeEach(async () => {
+    root = await fs.mkdtemp(path.join(os.tmpdir(), "openclaw-replay-"));
+  });
+  afterEach(async () => {
+    await fs.rm(root, { recursive: true, force: true });
+  });
+  const call = (source: string, target: string): number =>
+    replayRecentUserAssistantMessages({
+      sourceTranscript: source,
+      targetTranscript: target,
+      newSessionId: "new-session",
+    });
+
+  it("replays only the user/assistant tail and skips tool/system/malformed records", async () => {
+    const source = path.join(root, "prev.jsonl");
+    const target = path.join(root, "next.jsonl");
+    const lines: string[] = [j({ type: "session", id: "old" })];
+    for (let i = 0; i < DEFAULT_REPLAY_MAX_MESSAGES + 4; i += 1) {
+      lines.push(j({ message: { role: i % 2 === 0 ? "user" : "assistant", content: `m${i}` } }));
+    }
+    lines.push(j({ message: { role: "tool" } }));
+    lines.push(j({ type: "compaction", timestamp: new Date().toISOString() }));
+    lines.push("not-json-line\n");
+    await fs.writeFile(source, lines.join(""), "utf8");
+
+    expect(call(source, target)).toBe(DEFAULT_REPLAY_MAX_MESSAGES);
+    const records = (await fs.readFile(target, "utf8"))
+      .split(/\r?\n/)
+      .filter((line) => line.trim().length > 0)
+      .map((line) => JSON.parse(line));
+    expect(records[0]).toMatchObject({ type: "session", id: "new-session" });
+    expect(records).toHaveLength(1 + DEFAULT_REPLAY_MAX_MESSAGES);
+    for (const r of records.slice(1)) {
+      expect(["user", "assistant"]).toContain(r.message.role);
+    }
+    expect(call(path.join(root, "missing.jsonl"), path.join(root, "out.jsonl"))).toBe(0);
+  });
+});
diff --git a/src/auto-reply/reply/session-transcript-replay.ts b/src/auto-reply/reply/session-transcript-replay.ts
new file mode 100644
index 00000000000..e40fdb38b94
--- /dev/null
+++ b/src/auto-reply/reply/session-transcript-replay.ts
@@ -0,0 +1,64 @@
+import fs from "node:fs";
+import path from "node:path";
+import { CURRENT_SESSION_VERSION } from "@mariozechner/pi-coding-agent";
+
+/** Tail kept so DM continuity survives silent session rotations. */
+export const DEFAULT_REPLAY_MAX_MESSAGES = 6;
+
+type SessionRecord = { message?: { role?: unknown } };
+
+/**
+ * Copy the tail of user/assistant JSONL records from a prior transcript into a
+ * freshly-rotated one. Tool, system, and compaction records are skipped so
+ * replay cannot reshape tool/role ordering. Returns 0 on any error.
+ */
+export function replayRecentUserAssistantMessages(params: {
+  sourceTranscript?: string;
+  targetTranscript: string;
+  newSessionId: string;
+  maxMessages?: number;
+}): number {
+  const max = Math.max(0, params.maxMessages ?? DEFAULT_REPLAY_MAX_MESSAGES);
+  const src = params.sourceTranscript;
+  if (max === 0 || !src || !fs.existsSync(src)) {
+    return 0;
+  }
+  try {
+    const kept: string[] = [];
+    for (const line of fs.readFileSync(src, "utf-8").split(/\r?\n/)) {
+      if (!line.trim()) {
+        continue;
+      }
+      try {
+        const role = (JSON.parse(line) as SessionRecord | null)?.message?.role;
+        if (role === "user" || role === "assistant") {
+          kept.push(line);
+        }
+      } catch {
+        // Skip malformed lines.
+      }
+    }
+    if (kept.length === 0) {
+      return 0;
+    }
+    if (!fs.existsSync(params.targetTranscript)) {
+      fs.mkdirSync(path.dirname(params.targetTranscript), { recursive: true });
+      const header = JSON.stringify({
+        type: "session",
+        version: CURRENT_SESSION_VERSION,
+        id: params.newSessionId,
+        timestamp: new Date().toISOString(),
+        cwd: process.cwd(),
+      });
+      fs.writeFileSync(params.targetTranscript, `${header}\n`, { encoding: "utf-8", mode: 0o600 });
+    }
+    const tail = kept.slice(-max);
+    fs.appendFileSync(params.targetTranscript, `${tail.join("\n")}\n`, {
+      encoding: "utf-8",
+      mode: 0o600,
+    });
+    return tail.length;
+  } catch {
+    return 0;
+  }
+}