diff --git a/codex-rs/sandboxing/src/bwrap.rs b/codex-rs/sandboxing/src/bwrap.rs
index 3435c6d19..840bb3e62 100644
--- a/codex-rs/sandboxing/src/bwrap.rs
+++ b/codex-rs/sandboxing/src/bwrap.rs
@@ -1,9 +1,16 @@
 use crate::policy_transforms::should_require_platform_sandbox;
 use codex_protocol::models::PermissionProfile;
+use std::io::ErrorKind;
+use std::io::Read;
+use std::os::fd::AsRawFd;
 use std::path::Path;
 use std::path::PathBuf;
 use std::process::Command;
 use std::process::Output;
+use std::process::Stdio;
+use std::thread;
+use std::time::Duration;
+use std::time::Instant;
 
 const SYSTEM_BWRAP_PROGRAM: &str = "bwrap";
 const MISSING_BWRAP_WARNING: &str = concat!(
@@ -26,6 +33,9 @@ const USER_NAMESPACE_FAILURES: [&str; 4] = [
     "setting up uid map: Permission denied",
     "No permissions to create a new namespace",
 ];
+const SYSTEM_BWRAP_PROBE_TIMEOUT: Duration = Duration::from_millis(500);
+const SYSTEM_BWRAP_PROBE_POLL_INTERVAL: Duration = Duration::from_millis(50);
+const SYSTEM_BWRAP_PROBE_STDERR_LIMIT_BYTES: u64 = 64 * 1024;
 
 pub fn system_bwrap_warning(permission_profile: &PermissionProfile) -> Option<String> {
     if !should_warn_about_system_bwrap(permission_profile) {
@@ -54,15 +64,15 @@ fn system_bwrap_warning_for_path(system_bwrap_path: Option<&Path>) -> Option<Str
         return Some(MISSING_BWRAP_WARNING.to_string());
     };
 
-    if !system_bwrap_has_user_namespace_access(system_bwrap_path) {
+    if !system_bwrap_has_user_namespace_access(system_bwrap_path, SYSTEM_BWRAP_PROBE_TIMEOUT) {
         return Some(USER_NAMESPACE_WARNING.to_string());
     }
 
     None
 }
 
-fn system_bwrap_has_user_namespace_access(system_bwrap_path: &Path) -> bool {
-    let output = match Command::new(system_bwrap_path)
+fn system_bwrap_has_user_namespace_access(system_bwrap_path: &Path, timeout: Duration) -> bool {
+    let mut child = match Command::new(system_bwrap_path)
         .args([
             "--unshare-user",
             "--unshare-net",
@@ -71,13 +81,58 @@ fn system_bwrap_has_user_namespace_access(system_bwrap_path: &Path) -> bool {
             "/",
             "/bin/true",
         ])
-        .output()
+        .stdout(Stdio::null())
+        .stderr(Stdio::piped())
+        .spawn()
     {
-        Ok(output) => output,
+        Ok(child) => child,
         Err(_) => return true,
     };
 
-    output.status.success() || !is_user_namespace_failure(&output)
+    let deadline = Instant::now() + timeout;
+    loop {
+        match child.try_wait() {
+            Ok(Some(status)) => {
+                let stderr = child.stderr.take().map_or_else(Vec::new, |stderr| {
+                    let fd = stderr.as_raw_fd();
+                    let flags = unsafe { libc::fcntl(fd, libc::F_GETFL) };
+                    if flags < 0
+                        || unsafe { libc::fcntl(fd, libc::F_SETFL, flags | libc::O_NONBLOCK) } < 0
+                    {
+                        return Vec::new();
+                    }
+
+                    let mut bytes = Vec::new();
+                    let mut stderr = stderr.take(SYSTEM_BWRAP_PROBE_STDERR_LIMIT_BYTES);
+                    if let Err(err) = stderr.read_to_end(&mut bytes)
+                        && err.kind() != ErrorKind::WouldBlock
+                    {
+                        return bytes;
+                    }
+                    bytes
+                });
+                let output = Output {
+                    status,
+                    stdout: Vec::new(),
+                    stderr,
+                };
+                return output.status.success() || !is_user_namespace_failure(&output);
+            }
+            Ok(None) => {
+                if Instant::now() >= deadline {
+                    let _ = child.kill();
+                    let _ = child.wait();
+                    return true;
+                }
+                thread::sleep(SYSTEM_BWRAP_PROBE_POLL_INTERVAL);
+            }
+            Err(_) => {
+                let _ = child.kill();
+                let _ = child.wait();
+                return true;
+            }
+        }
+    }
 }
 
 pub(crate) fn is_wsl1() -> bool {
diff --git a/codex-rs/sandboxing/src/bwrap_tests.rs b/codex-rs/sandboxing/src/bwrap_tests.rs
index f36848e1e..3c7a50392 100644
--- a/codex-rs/sandboxing/src/bwrap_tests.rs
+++ b/codex-rs/sandboxing/src/bwrap_tests.rs
@@ -2,6 +2,8 @@ use super::*;
 use pretty_assertions::assert_eq;
 use std::path::Path;
 use std::path::PathBuf;
+use std::time::Duration;
+use std::time::Instant;
 use tempfile::tempdir;
 
 #[test]
@@ -44,6 +46,43 @@ exit 1
     assert_eq!(system_bwrap_warning_for_path(Some(fake_bwrap_path)), None);
 }
 
+#[test]
+fn system_bwrap_probe_times_out_without_reporting_a_warning() {
+    let fake_bwrap = write_fake_bwrap(
+        r#"#!/bin/sh
+sleep 1
+exit 0
+"#,
+    );
+    let fake_bwrap_path: &Path = fake_bwrap.as_ref();
+    let started_at = Instant::now();
+
+    assert!(system_bwrap_has_user_namespace_access(
+        fake_bwrap_path,
+        Duration::from_millis(10),
+    ));
+    assert!(started_at.elapsed() < Duration::from_millis(500));
+}
+
+#[test]
+fn system_bwrap_probe_does_not_wait_for_descendants_holding_stderr_open() {
+    let fake_bwrap = write_fake_bwrap(
+        r#"#!/bin/sh
+echo 'No permissions to create a new namespace' >&2
+sleep 1 &
+exit 1
+"#,
+    );
+    let fake_bwrap_path: &Path = fake_bwrap.as_ref();
+    let started_at = Instant::now();
+
+    assert!(!system_bwrap_has_user_namespace_access(
+        fake_bwrap_path,
+        Duration::from_millis(100),
+    ));
+    assert!(started_at.elapsed() < Duration::from_millis(500));
+}
+
 #[test]
 fn detects_wsl1_proc_version_formats() {
     assert!(proc_version_indicates_wsl1(