diff --git a/codex-rs/core/src/session/turn.rs b/codex-rs/core/src/session/turn.rs
index 560d04e88d..d3f8733379 100644
--- a/codex-rs/core/src/session/turn.rs
+++ b/codex-rs/core/src/session/turn.rs
@@ -1932,6 +1932,7 @@ async fn try_run_sampling_request(
                     )
                     .await
                 {
+                    crate::guardian::enqueue_proactive_guardian_trunk_sync(&sess, &turn_context);
                     continue;
                 }
 
@@ -1968,6 +1969,7 @@ async fn try_run_sampling_request(
                         Ok(output_result) => output_result,
                         Err(err) => break Err(err),
                     };
+                crate::guardian::enqueue_proactive_guardian_trunk_sync(&sess, &turn_context);
                 if let Some(tool_future) = output_result.tool_future {
                     in_flight.push_back(tool_future);
                 }
diff --git a/codex-rs/core/src/stream_events_utils.rs b/codex-rs/core/src/stream_events_utils.rs
index 06797e6058..5a31d18020 100644
--- a/codex-rs/core/src/stream_events_utils.rs
+++ b/codex-rs/core/src/stream_events_utils.rs
@@ -342,8 +342,6 @@ pub(crate) async fn handle_output_item_done(
         }
     }
 
-    crate::guardian::enqueue_proactive_guardian_trunk_sync(&ctx.sess, &ctx.turn_context);
-
     Ok(output)
 }