diff --git a/codex-rs/core/src/tools/orchestrator.rs b/codex-rs/core/src/tools/orchestrator.rs
index bdc4e3aff70..38aac5c1edf 100644
--- a/codex-rs/core/src/tools/orchestrator.rs
+++ b/codex-rs/core/src/tools/orchestrator.rs
@@ -98,9 +98,9 @@ impl ToolOrchestrator {
                         "sandbox denied and no retry".to_string(),
                     ));
                 }
-                // Under `Never`, do not retry without sandbox; surface a concise message
+                // Under `Never` or `OnRequest`, do not retry without sandbox; surface a concise message
                 // derived from the actual output (platform-agnostic).
-                if matches!(approval_policy, AskForApproval::Never) {
+                if !tool.wants_no_sandbox_approval(approval_policy) {
                     let msg = build_never_denied_message_from_output(output.as_ref());
                     return Err(ToolError::SandboxDenied(msg));
                 }
diff --git a/codex-rs/core/src/tools/runtimes/apply_patch.rs b/codex-rs/core/src/tools/runtimes/apply_patch.rs
index eb1cda4e5b2..18abbfee4a4 100644
--- a/codex-rs/core/src/tools/runtimes/apply_patch.rs
+++ b/codex-rs/core/src/tools/runtimes/apply_patch.rs
@@ -17,6 +17,7 @@ use crate::tools::sandboxing::ToolCtx;
 use crate::tools::sandboxing::ToolError;
 use crate::tools::sandboxing::ToolRuntime;
 use crate::tools::sandboxing::with_cached_approval;
+use codex_protocol::protocol::AskForApproval;
 use codex_protocol::protocol::ReviewDecision;
 use futures::future::BoxFuture;
 use std::collections::HashMap;
@@ -127,6 +128,10 @@ impl Approvable<ApplyPatchRequest> for ApplyPatchRuntime {
             .await
         })
     }
+
+    fn wants_no_sandbox_approval(&self, policy: AskForApproval) -> bool {
+        !matches!(policy, AskForApproval::Never)
+    }
 }
 
 impl ToolRuntime<ApplyPatchRequest, ExecToolCallOutput> for ApplyPatchRuntime {
diff --git a/codex-rs/core/src/tools/sandboxing.rs b/codex-rs/core/src/tools/sandboxing.rs
index 7c4d65ca800..0dd7a99f470 100644
--- a/codex-rs/core/src/tools/sandboxing.rs
+++ b/codex-rs/core/src/tools/sandboxing.rs
@@ -121,6 +121,11 @@ pub(crate) trait Approvable<Req> {
         }
     }
 
+    /// Decide we can request an approval for no-sandbox execution.
+    fn wants_no_sandbox_approval(&self, policy: AskForApproval) -> bool {
+        !matches!(policy, AskForApproval::Never | AskForApproval::OnRequest)
+    }
+
     fn start_approval_async<'a>(
         &'a mut self,
         req: &'a Req,