diff --git a/src/node/services/agentSession.autoCompaction.test.ts b/src/node/services/agentSession.autoCompaction.test.ts
index 53ceb0d016..5b6082648b 100644
--- a/src/node/services/agentSession.autoCompaction.test.ts
+++ b/src/node/services/agentSession.autoCompaction.test.ts
@@ -151,8 +151,9 @@ describe("AgentSession on-send auto-compaction snapshot deferral", () => {
         muxMetadata: compactionMetadata,
       }
     );
-    const snapshot = createMuxMessage("file-change", "user", "<file-change />", {
+    const snapshot = createMuxMessage("file-snapshot", "user", "@foo.ts contents", {
       synthetic: true,
+      fileAtMentionSnapshot: ["t0"],
     });
     const internals = session as unknown as {
       resolveCompactionRequest: (
@@ -176,6 +177,104 @@ describe("AgentSession on-send auto-compaction snapshot deferral", () => {
     session.dispose();
   });
 
+  test("tracks a pending compaction request across a crash-recovery [CONTINUE] sentinel", async () => {
+    const model = "openai:gpt-4o";
+    const { session } = await createSessionHarness({
+      workspaceId: "ws-auto-compaction-request-continue-sentinel",
+    });
+    const compactionMetadata = {
+      type: "compaction-request" as const,
+      rawCommand: "/compact",
+      parsed: {},
+    };
+    const compactionRequest = createMuxMessage(
+      "compaction-request",
+      "user",
+      "Summarize the conversation",
+      {
+        synthetic: true,
+        muxMetadata: compactionMetadata,
+      }
+    );
+    // Crash mid-compaction persists an orphaned assistant row; recovery appends a
+    // synthetic [CONTINUE] sentinel after it. The resumed stream sends without
+    // compaction options but must still correlate with the pending request.
+    const orphanedAssistant = createMuxMessage("orphaned-summary", "assistant", "## Summary", {});
+    const continueSentinel = createMuxMessage("continue-sentinel", "user", "[CONTINUE]", {
+      synthetic: true,
+    });
+    const internals = session as unknown as {
+      resolveCompactionRequest: (
+        history: MuxMessage[],
+        modelString: string,
+        options?: SendMessageOptions
+      ) => { id: string } | undefined;
+    };
+
+    const request = internals.resolveCompactionRequest(
+      [compactionRequest, orphanedAssistant, continueSentinel],
+      model,
+      { model, agentId: "default" }
+    );
+
+    expect(request).toMatchObject({ id: compactionRequest.id });
+
+    // A real user message after the request must stop correlation.
+    const realUser = createMuxMessage("real-user", "user", "thanks", {});
+    const stopped = internals.resolveCompactionRequest(
+      [compactionRequest, orphanedAssistant, continueSentinel, realUser],
+      model,
+      { model, agentId: "default" }
+    );
+    expect(stopped).toBeUndefined();
+
+    session.dispose();
+  });
+
+  test("does not correlate a stale compaction request past unrelated synthetic turns", async () => {
+    const model = "openai:gpt-4o";
+    const { session } = await createSessionHarness({
+      workspaceId: "ws-auto-compaction-stale-request-stop",
+    });
+    const compactionMetadata = {
+      type: "compaction-request" as const,
+      rawCommand: "/compact",
+      parsed: {},
+    };
+    // Failed summary: request stays in history with no boundary committed.
+    const staleRequest = createMuxMessage(
+      "stale-compaction-request",
+      "user",
+      "Summarize the conversation",
+      {
+        synthetic: true,
+        muxMetadata: compactionMetadata,
+      }
+    );
+    const orphanedAssistant = createMuxMessage("orphaned-summary", "assistant", "", {});
+    // An unrecognized synthetic turn (e.g. goal continuation) after the failed
+    // summary must stop correlation instead of claiming the stale request.
+    const goalContinuation = createMuxMessage("goal-wake", "user", "continue the goal", {
+      synthetic: true,
+    });
+    const internals = session as unknown as {
+      resolveCompactionRequest: (
+        history: MuxMessage[],
+        modelString: string,
+        options?: SendMessageOptions
+      ) => { id: string } | undefined;
+    };
+
+    const stopped = internals.resolveCompactionRequest(
+      [staleRequest, orphanedAssistant, goalContinuation],
+      model,
+      { model, agentId: "default" }
+    );
+    expect(stopped).toBeUndefined();
+
+    session.dispose();
+  });
+
   test("does not materialize skill snapshots (or run their directives) on deferred on-send compaction turns", async () => {
     const workspaceId = "ws-auto-compaction-skill-snapshot-deferral";
 
diff --git a/src/node/services/agentSession.ts b/src/node/services/agentSession.ts
index 49bfc60093..99453138f5 100644
--- a/src/node/services/agentSession.ts
+++ b/src/node/services/agentSession.ts
@@ -408,6 +408,32 @@ function isCompactionRequestMetadata(meta: unknown): meta is CompactionRequestMe
   return true;
 }
 
+/**
+ * Synthetic user rows that may legitimately sit between a pending compaction
+ * request and its summary stream: file @-mention prompt snapshots, turn-start
+ * file-change notifications, and the crash-recovery [CONTINUE] sentinel.
+ *
+ * Any other user row stops backward correlation. A summary stream that fails
+ * validation (empty or raw-JSON output) commits no boundary, so its request
+ * stays in history; letting unrelated synthetic turns (goal continuations,
+ * task wakes) traverse past it would persist their responses as compaction
+ * boundaries and collapse valid history.
+ */
+function canFollowPendingCompactionRequest(message: MuxMessage): boolean {
+  if (message.metadata?.synthetic !== true) {
+    return false;
+  }
+  if (message.metadata?.fileAtMentionSnapshot != null) {
+    return true;
+  }
+  const text =
+    message.parts
+      ?.filter((part) => part.type === "text")
+      .map((part) => part.text)
+      .join("\n") ?? "";
+  return text.startsWith("<system-file-update>") || text === "[CONTINUE]";
+}
+
 const AUTO_RETRY_PREFERENCE_FILE = "auto-retry-preference.json";
 
 /**
@@ -4828,8 +4854,6 @@ export class AgentSession {
         source?: "idle-compaction" | "auto-compaction";
       }
     | undefined {
-    const streamIsCompaction = isCompactionRequestMetadata(options?.muxMetadata);
-
     for (let index = history.length - 1; index >= 0; index -= 1) {
       const message = history[index];
       if (message.role !== "user") {
@@ -4845,9 +4869,11 @@ export class AgentSession {
         };
       }
 
-      // Snapshot rows can follow a synthetic compaction request before stream startup.
-      // Skip only those rows when the current send options identify this stream as compaction.
-      if (!streamIsCompaction || message.metadata?.synthetic !== true) {
+      // Only recognized synthetic rows may sit between a pending compaction
+      // request and its stream; anything else stops correlation so a stale
+      // request cannot claim an unrelated later turn (see
+      // canFollowPendingCompactionRequest).
+      if (!canFollowPendingCompactionRequest(message)) {
         return undefined;
       }
     }