diff --git a/src/auto-reply/reply/agent-runner-session-reset.ts b/src/auto-reply/reply/agent-runner-session-reset.ts
index 46cfc2efbee..55df3cbc5a1 100644
--- a/src/auto-reply/reply/agent-runner-session-reset.ts
+++ b/src/auto-reply/reply/agent-runner-session-reset.ts
@@ -99,7 +99,7 @@ export async function resetReplyRunSession(params: {
   }
   // Silent rotations (compaction/role-ordering) fire without user intent, so
   // preserve recent user/assistant turns for direct-chat continuity.
-  replayRecentUserAssistantMessages({
+  await replayRecentUserAssistantMessages({
     sourceTranscript: prevEntry.sessionFile,
     targetTranscript: nextSessionFile,
     newSessionId: nextSessionId,
diff --git a/src/auto-reply/reply/session-transcript-replay.test.ts b/src/auto-reply/reply/session-transcript-replay.test.ts
index 20c754623dd..e670dec4c66 100644
--- a/src/auto-reply/reply/session-transcript-replay.test.ts
+++ b/src/auto-reply/reply/session-transcript-replay.test.ts
@@ -17,7 +17,7 @@ describe("replayRecentUserAssistantMessages", () => {
   afterEach(async () => {
     await fs.rm(root, { recursive: true, force: true });
   });
-  const call = (source: string, target: string): number =>
+  const call = (source: string, target: string): Promise<number> =>
     replayRecentUserAssistantMessages({
       sourceTranscript: source,
       targetTranscript: target,
@@ -36,7 +36,7 @@ describe("replayRecentUserAssistantMessages", () => {
     lines.push("not-json-line\n");
     await fs.writeFile(source, lines.join(""), "utf8");
 
-    expect(call(source, target)).toBe(DEFAULT_REPLAY_MAX_MESSAGES);
+    expect(await call(source, target)).toBe(DEFAULT_REPLAY_MAX_MESSAGES);
     const records = (await fs.readFile(target, "utf8"))
       .split(/\r?\n/)
       .filter((line) => line.trim().length > 0)
@@ -46,6 +46,26 @@ describe("replayRecentUserAssistantMessages", () => {
     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);
+    expect(await call(path.join(root, "missing.jsonl"), path.join(root, "out.jsonl"))).toBe(0);
+  });
+
+  it("skips header for pre-existing targets and aligns the tail to a user turn", async () => {
+    const source = path.join(root, "prev.jsonl");
+    const target = path.join(root, "next.jsonl");
+    await fs.writeFile(target, j({ type: "session", id: "existing" }), "utf8");
+    const lines: string[] = [];
+    for (let i = 0; i < DEFAULT_REPLAY_MAX_MESSAGES + 1; i += 1) {
+      lines.push(j({ message: { role: i % 2 === 0 ? "user" : "assistant", content: `m${i}` } }));
+    }
+    await fs.writeFile(source, lines.join(""), "utf8");
+
+    expect(await call(source, target)).toBe(DEFAULT_REPLAY_MAX_MESSAGES - 1);
+    const records = (await fs.readFile(target, "utf8"))
+      .split(/\r?\n/)
+      .filter((line) => line.trim().length > 0)
+      .map((line) => JSON.parse(line));
+    expect(records.filter((r) => r.type === "session")).toHaveLength(1);
+    expect(records[0]).toMatchObject({ id: "existing" });
+    expect(records[1].message.role).toBe("user");
   });
 });
diff --git a/src/auto-reply/reply/session-transcript-replay.ts b/src/auto-reply/reply/session-transcript-replay.ts
index e40fdb38b94..5af998e0c8d 100644
--- a/src/auto-reply/reply/session-transcript-replay.ts
+++ b/src/auto-reply/reply/session-transcript-replay.ts
@@ -1,4 +1,5 @@
 import fs from "node:fs";
+import fsp from "node:fs/promises";
 import path from "node:path";
 import { CURRENT_SESSION_VERSION } from "@mariozechner/pi-coding-agent";
 
@@ -6,33 +7,37 @@ import { CURRENT_SESSION_VERSION } from "@mariozechner/pi-coding-agent";
 export const DEFAULT_REPLAY_MAX_MESSAGES = 6;
 
 type SessionRecord = { message?: { role?: unknown } };
+type KeptRecord = { role: "user" | "assistant"; line: string };
 
 /**
  * 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.
+ * replay cannot reshape tool/role ordering, and the tail is aligned to start
+ * with a user turn so role-ordering resets cannot immediately recur. Uses
+ * async I/O so long transcripts do not block the event loop. Returns 0 on
+ * any error.
  */
-export function replayRecentUserAssistantMessages(params: {
+export async function replayRecentUserAssistantMessages(params: {
   sourceTranscript?: string;
   targetTranscript: string;
   newSessionId: string;
   maxMessages?: number;
-}): number {
+}): Promise<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/)) {
+    const kept: KeptRecord[] = [];
+    for (const line of (await fsp.readFile(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);
+          kept.push({ role, line });
         }
       } catch {
         // Skip malformed lines.
@@ -41,8 +46,13 @@ export function replayRecentUserAssistantMessages(params: {
     if (kept.length === 0) {
       return 0;
     }
+    let startIdx = Math.max(0, kept.length - max);
+    while (startIdx < kept.length - 1 && kept[startIdx].role === "assistant") {
+      startIdx += 1;
+    }
+    const tail = kept.slice(startIdx).map((entry) => entry.line);
     if (!fs.existsSync(params.targetTranscript)) {
-      fs.mkdirSync(path.dirname(params.targetTranscript), { recursive: true });
+      await fsp.mkdir(path.dirname(params.targetTranscript), { recursive: true });
       const header = JSON.stringify({
         type: "session",
         version: CURRENT_SESSION_VERSION,
@@ -50,13 +60,12 @@ export function replayRecentUserAssistantMessages(params: {
         timestamp: new Date().toISOString(),
         cwd: process.cwd(),
       });
-      fs.writeFileSync(params.targetTranscript, `${header}\n`, { encoding: "utf-8", mode: 0o600 });
+      await fsp.writeFile(params.targetTranscript, `${header}\n`, {
+        encoding: "utf-8",
+        mode: 0o600,
+      });
     }
-    const tail = kept.slice(-max);
-    fs.appendFileSync(params.targetTranscript, `${tail.join("\n")}\n`, {
-      encoding: "utf-8",
-      mode: 0o600,
-    });
+    await fsp.appendFile(params.targetTranscript, `${tail.join("\n")}\n`, "utf-8");
     return tail.length;
   } catch {
     return 0;