diff --git a/src/auto-reply/reply/session-transcript-replay.test.ts b/src/auto-reply/reply/session-transcript-replay.test.ts
index aede8e95541..76d83a62a89 100644
--- a/src/auto-reply/reply/session-transcript-replay.test.ts
+++ b/src/auto-reply/reply/session-transcript-replay.test.ts
@@ -77,4 +77,39 @@ describe("replayRecentUserAssistantMessages", () => {
     expect(records[0]).toMatchObject({ id: "existing" });
     expect(records[1].message.role).toBe("user");
   });
+
+  it("coalesces same-role runs so replayed records strictly alternate", async () => {
+    const source = path.join(root, "prev.jsonl");
+    const target = path.join(root, "next.jsonl");
+    await fs.writeFile(
+      source,
+      [
+        j({ message: { role: "user", content: "older user" } }),
+        j({ message: { role: "user", content: "latest user" } }),
+        j({ message: { role: "assistant", content: "older assistant" } }),
+        j({ message: { role: "assistant", content: "latest assistant" } }),
+        j({ message: { role: "user", content: "follow-up" } }),
+        j({ message: { role: "assistant", content: "answer" } }),
+      ].join(""),
+      "utf8",
+    );
+
+    expect(await call(source, target)).toBe(4);
+    const records = (await fs.readFile(target, "utf8"))
+      .split(/\r?\n/)
+      .filter((line) => line.trim().length > 0)
+      .map((line) => JSON.parse(line));
+    expect(records.slice(1).map((r) => r.message.role)).toEqual([
+      "user",
+      "assistant",
+      "user",
+      "assistant",
+    ]);
+    expect(records.slice(1).map((r) => r.message.content)).toEqual([
+      "latest user",
+      "latest assistant",
+      "follow-up",
+      "answer",
+    ]);
+  });
 });
diff --git a/src/auto-reply/reply/session-transcript-replay.ts b/src/auto-reply/reply/session-transcript-replay.ts
index dfc5661810b..b7afdbc9763 100644
--- a/src/auto-reply/reply/session-transcript-replay.ts
+++ b/src/auto-reply/reply/session-transcript-replay.ts
@@ -12,10 +12,10 @@ 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, 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.
+ * replay cannot reshape tool/role ordering, and the tail is aligned and
+ * coalesced into alternating user/assistant turns 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 async function replayRecentUserAssistantMessages(params: {
   sourceTranscript?: string;
@@ -55,7 +55,7 @@ export async function replayRecentUserAssistantMessages(params: {
       // role-ordering hazard this reset path is recovering from.
       return 0;
     }
-    const tail = kept.slice(startIdx).map((entry) => entry.line);
+    const tail = coalesceAlternatingReplayTail(kept.slice(startIdx)).map((entry) => entry.line);
     if (!fs.existsSync(params.targetTranscript)) {
       await fsp.mkdir(path.dirname(params.targetTranscript), { recursive: true });
       const header = JSON.stringify({
@@ -76,3 +76,18 @@ export async function replayRecentUserAssistantMessages(params: {
     return 0;
   }
 }
+
+// Keep the newest record from each same-role run, preserving original JSONL bytes
+// for replay while ensuring strict provider alternation.
+function coalesceAlternatingReplayTail(entries: KeptRecord[]): KeptRecord[] {
+  const tail: KeptRecord[] = [];
+  for (const entry of entries) {
+    const lastIdx = tail.length - 1;
+    if (lastIdx >= 0 && tail[lastIdx]?.role === entry.role) {
+      tail[lastIdx] = entry;
+      continue;
+    }
+    tail.push(entry);
+  }
+  return tail;
+}