diff --git a/src/agents/command/attempt-execution.cli.test.ts b/src/agents/command/attempt-execution.cli.test.ts
index 2f3be0c11ff4..4cd444e6ec93 100644
--- a/src/agents/command/attempt-execution.cli.test.ts
+++ b/src/agents/command/attempt-execution.cli.test.ts
@@ -1314,6 +1314,17 @@ describe("CLI attempt execution", () => {
       );
       await replaceSessionEntry({ sessionKey, storePath }, concurrentEntry);
       sessionStore[sessionKey] = concurrentEntry;
+      const clearBeforeFreshRetry = runArgs.onBeforeFreshCliSessionRetry;
+      expect(clearBeforeFreshRetry).toBeTypeOf("function");
+      await expect(
+        (
+          clearBeforeFreshRetry as (params: {
+            provider: string;
+            reason: "timeout";
+            sessionId: string;
+          }) => Promise<boolean>
+        )({ provider: "claude-cli", reason: "timeout", sessionId: forkedCliSessionId }),
+      ).resolves.toBe(false);
       throw recoveryError;
     });
 
diff --git a/src/agents/command/session-store.ts b/src/agents/command/session-store.ts
index b0abbffbe5f4..3f6ce6cadb5b 100644
--- a/src/agents/command/session-store.ts
+++ b/src/agents/command/session-store.ts
@@ -337,6 +337,7 @@ export async function clearCliSessionInStore(params: {
     return undefined;
   }
 
+  let didClear = false;
   const persisted = await patchSessionEntry(
     {
       storePath,
@@ -358,14 +359,16 @@ export async function clearCliSessionInStore(params: {
       const next = { ...currentEntry };
       clearCliSession(next, provider);
       next.updatedAt = Date.now();
+      didClear = true;
       return next;
     },
     { fallbackEntry: entry },
   );
-  if (persisted) {
+  if (persisted && didClear) {
     sessionStore[sessionKey] = persisted;
+    return persisted;
   }
-  return persisted ?? undefined;
+  return undefined;
 }
 
 /** Clears the one-shot fork marker before the resumed CLI process starts. */