diff --git a/codex-rs/core/src/exec_policy.rs b/codex-rs/core/src/exec_policy.rs
index 3574ee77fd..a44ffbe3ab 100644
--- a/codex-rs/core/src/exec_policy.rs
+++ b/codex-rs/core/src/exec_policy.rs
@@ -649,9 +649,6 @@ pub(crate) fn render_decision_for_unmatched_command(
             codex_shell_command::is_safe_command::is_safe_powershell_words(command)
         }
     };
-    if is_known_safe && !used_complex_parsing {
-        return Decision::Allow;
-    }
 
     // On Windows, ReadOnly sandbox is not a real sandbox, so special-case it
     // here.
@@ -662,6 +659,14 @@ pub(crate) fn render_decision_for_unmatched_command(
             sandbox_cwd,
         );
 
+    if is_known_safe
+        && !used_complex_parsing
+        && (approval_policy == AskForApproval::UnlessTrusted
+            || environment_lacks_sandbox_protections)
+    {
+        return Decision::Allow;
+    }
+
     // If the command is flagged as dangerous or we have no sandbox protection,
     // we should never allow it to run without approval.
     //
diff --git a/codex-rs/core/src/exec_policy_tests.rs b/codex-rs/core/src/exec_policy_tests.rs
index 96c32c4491..f15c0280b0 100644
--- a/codex-rs/core/src/exec_policy_tests.rs
+++ b/codex-rs/core/src/exec_policy_tests.rs
@@ -1144,6 +1144,29 @@ fn unmatched_on_request_uses_split_filesystem_policy_for_escalation_prompts() {
     );
 }
 
+#[test]
+fn known_safe_on_request_still_prompts_for_restricted_sandbox_escalation() {
+    let command = vec!["echo".to_string(), "hello".to_string()];
+
+    assert_eq!(
+        Decision::Prompt,
+        render_decision_for_unmatched_command(
+            &command,
+            UnmatchedCommandContext {
+                approval_policy: AskForApproval::OnRequest,
+                permission_profile: &permission_profile_from_sandbox_policy(
+                    &SandboxPolicy::new_workspace_write_policy(),
+                ),
+                file_system_sandbox_policy: &workspace_write_file_system_sandbox_policy(),
+                sandbox_cwd: Path::new("/tmp"),
+                sandbox_permissions: SandboxPermissions::RequireEscalated,
+                used_complex_parsing: false,
+                command_origin: ExecPolicyCommandOrigin::Generic,
+            },
+        )
+    );
+}
+
 #[test]
 fn managed_cwd_write_profile_is_not_read_only() {
     let file_system_sandbox_policy = FileSystemSandboxPolicy::restricted(vec![
@@ -1230,6 +1253,55 @@ async fn exec_approval_requirement_prompts_for_inline_additional_permissions_und
     .await;
 }
 
+#[tokio::test]
+async fn exec_approval_requirement_prompts_for_known_safe_escalation_under_on_request() {
+    assert_exec_approval_requirement_for_command(
+        ExecApprovalRequirementScenario {
+            policy_src: None,
+            command: vec!["echo".to_string(), "hello".to_string()],
+            approval_policy: AskForApproval::OnRequest,
+            sandbox_policy: SandboxPolicy::new_workspace_write_policy(),
+            file_system_sandbox_policy: workspace_write_file_system_sandbox_policy(),
+            sandbox_permissions: SandboxPermissions::RequireEscalated,
+            prefix_rule: None,
+        },
+        ExecApprovalRequirement::NeedsApproval {
+            reason: None,
+            proposed_execpolicy_amendment: Some(ExecPolicyAmendment::new(vec![
+                "echo".to_string(),
+                "hello".to_string(),
+            ])),
+        },
+    )
+    .await;
+}
+
+#[tokio::test]
+async fn exec_approval_requirement_rejects_known_safe_escalation_when_granular_sandbox_is_disabled()
+{
+    assert_exec_approval_requirement_for_command(
+        ExecApprovalRequirementScenario {
+            policy_src: None,
+            command: vec!["echo".to_string(), "hello".to_string()],
+            approval_policy: AskForApproval::Granular(GranularApprovalConfig {
+                sandbox_approval: false,
+                rules: true,
+                skill_approval: true,
+                request_permissions: true,
+                mcp_elicitations: true,
+            }),
+            sandbox_policy: SandboxPolicy::new_workspace_write_policy(),
+            file_system_sandbox_policy: workspace_write_file_system_sandbox_policy(),
+            sandbox_permissions: SandboxPermissions::RequireEscalated,
+            prefix_rule: None,
+        },
+        ExecApprovalRequirement::Forbidden {
+            reason: REJECT_SANDBOX_APPROVAL_REASON.to_string(),
+        },
+    )
+    .await;
+}
+
 #[tokio::test]
 async fn exec_approval_requirement_rejects_unmatched_sandbox_escalation_when_granular_sandbox_is_disabled()
  {
diff --git a/codex-rs/core/tests/suite/approvals.rs b/codex-rs/core/tests/suite/approvals.rs
index 10bbb852eb..6db6495933 100644
--- a/codex-rs/core/tests/suite/approvals.rs
+++ b/codex-rs/core/tests/suite/approvals.rs
@@ -15,6 +15,7 @@ use codex_protocol::protocol::AskForApproval;
 use codex_protocol::protocol::EventMsg;
 use codex_protocol::protocol::ExecApprovalRequestEvent;
 use codex_protocol::protocol::ExecPolicyAmendment;
+use codex_protocol::protocol::GranularApprovalConfig;
 use codex_protocol::protocol::Op;
 use codex_protocol::protocol::ReviewDecision;
 use codex_protocol::protocol::SandboxPolicy;
@@ -965,6 +966,46 @@ fn scenarios() -> Vec<ScenarioSpec> {
                 output_contains: "rejected by user",
             },
         },
+        ScenarioSpec {
+            name: "known_safe_escalation_on_request_requires_approval",
+            approval_policy: OnRequest,
+            sandbox_policy: workspace_write(false),
+            action: ActionKind::RunCommand {
+                command: "echo known-safe-escalation",
+            },
+            sandbox_permissions: SandboxPermissions::RequireEscalated,
+            features: vec![],
+            model_override: Some("gpt-5.2"),
+            outcome: Outcome::ExecApprovalWithAmendment {
+                decision: ReviewDecision::Denied,
+                expected_reason: None,
+                expected_execpolicy_amendment: Some(&["echo", "known-safe-escalation"]),
+            },
+            expectation: Expectation::CommandFailure {
+                output_contains: "rejected by user",
+            },
+        },
+        ScenarioSpec {
+            name: "known_safe_escalation_granular_sandbox_disabled_rejects",
+            approval_policy: Granular(GranularApprovalConfig {
+                sandbox_approval: false,
+                rules: true,
+                skill_approval: true,
+                request_permissions: true,
+                mcp_elicitations: true,
+            }),
+            sandbox_policy: workspace_write(false),
+            action: ActionKind::RunCommand {
+                command: "echo known-safe-escalation-granular-disabled",
+            },
+            sandbox_permissions: SandboxPermissions::RequireEscalated,
+            features: vec![],
+            model_override: Some("gpt-5.2"),
+            outcome: Outcome::Auto,
+            expectation: Expectation::CommandFailure {
+                output_contains: "you should not ask for escalated permissions",
+            },
+        },
         ScenarioSpec {
             name: "cat_heredoc_file_redirect_prefix_rule_requires_escalation_approval",
             approval_policy: OnRequest,