diff --git a/codex-rs/core/src/guardian/review.rs b/codex-rs/core/src/guardian/review.rs
index 385fe89ceb..a3c37b650a 100644
--- a/codex-rs/core/src/guardian/review.rs
+++ b/codex-rs/core/src/guardian/review.rs
@@ -317,6 +317,7 @@ async fn run_guardian_review(
         .config_layer_stack
         .requirements()
         .auto_review_required_for_model(&turn.model_info.slug)
+        && reasons.retry.is_none()
         && options
             .external_cancel
             .as_ref()
diff --git a/codex-rs/core/src/guardian/tests.rs b/codex-rs/core/src/guardian/tests.rs
index a2e7e267cc..c421c94dff 100644
--- a/codex-rs/core/src/guardian/tests.rs
+++ b/codex-rs/core/src/guardian/tests.rs
@@ -2981,6 +2981,72 @@ async fn guardian_review_does_not_retry_valid_denial() -> anyhow::Result<()> {
     Ok(())
 }
 
+#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+async fn escalated_retry_bypasses_extension_approval_and_runs_guardian() -> anyhow::Result<()> {
+    skip_if_no_network!(Ok(()));
+
+    struct AutoApprovingReviewContributor;
+
+    impl codex_extension_api::ApprovalReviewContributor for AutoApprovingReviewContributor {
+        fn contribute<'a>(
+            &'a self,
+            _session_store: &'a codex_extension_api::ExtensionData,
+            _thread_store: &'a codex_extension_api::ExtensionData,
+            _prompt: &'a str,
+        ) -> codex_extension_api::ExtensionFuture<'a, Option<ReviewDecision>> {
+            Box::pin(async move { Some(ReviewDecision::Approved) })
+        }
+    }
+
+    let server = start_mock_server().await;
+    let denial = serde_json::json!({
+        "risk_level": "high",
+        "user_authorization": "unknown",
+        "outcome": "deny",
+        "rationale": "The original attempt was blocked by the sandbox.",
+    })
+    .to_string();
+    let request_log = mount_sse_once(
+        &server,
+        sse(vec![
+            ev_response_created("resp-escalated-retry"),
+            ev_assistant_message("msg-escalated-retry", &denial),
+            ev_completed("resp-escalated-retry"),
+        ]),
+    )
+    .await;
+
+    let (mut session, turn) = guardian_test_session_and_turn(&server).await;
+    let mut extensions = codex_extension_api::ExtensionRegistryBuilder::<Config>::new();
+    extensions.approval_review_contributor(Arc::new(AutoApprovingReviewContributor));
+    Arc::get_mut(&mut session)
+        .expect("session should be uniquely owned")
+        .services
+        .extensions = Arc::new(extensions.build());
+    seed_guardian_parent_history(&session, &turn).await;
+
+    let retry_reason = "The sandbox blocked the original command.";
+    let decision = review_approval_request(
+        &session,
+        &turn,
+        "review-escalated-retry".to_string(),
+        guardian_shell_request("shell-escalated-retry"),
+        ApprovalRequestReasons {
+            approval: None,
+            retry: Some(retry_reason.to_string()),
+        },
+    )
+    .await;
+
+    assert!(matches!(decision, ReviewDecision::Denied { .. }));
+    assert!(
+        request_log
+            .single_request()
+            .body_contains_text(retry_reason)
+    );
+    Ok(())
+}
+
 #[tokio::test]
 async fn guardian_ephemeral_retry_preserves_parallel_trunk_and_fork_history() -> anyhow::Result<()>
 {