diff --git a/codex-rs/core/src/windows_sandbox.rs b/codex-rs/core/src/windows_sandbox.rs
index a1ff5dda09..d0fe013c7a 100644
--- a/codex-rs/core/src/windows_sandbox.rs
+++ b/codex-rs/core/src/windows_sandbox.rs
@@ -169,6 +169,41 @@ pub fn run_elevated_setup(
     )
 }
 
+#[cfg(target_os = "windows")]
+pub fn elevated_setup_is_ready(
+    permission_profile: &PermissionProfile,
+    workspace_roots: &[AbsolutePathBuf],
+    command_cwd: &Path,
+    env_map: &HashMap<String, String>,
+    codex_home: &Path,
+) -> bool {
+    if !sandbox_setup_is_complete(codex_home) {
+        return false;
+    }
+
+    codex_windows_sandbox::run_setup_refresh_with_extra_read_roots(
+        permission_profile,
+        workspace_roots,
+        command_cwd,
+        env_map,
+        codex_home,
+        Vec::new(),
+        /*proxy_enforced*/ false,
+    )
+    .is_ok()
+}
+
+#[cfg(not(target_os = "windows"))]
+pub fn elevated_setup_is_ready(
+    _permission_profile: &PermissionProfile,
+    _workspace_roots: &[AbsolutePathBuf],
+    _command_cwd: &Path,
+    _env_map: &HashMap<String, String>,
+    _codex_home: &Path,
+) -> bool {
+    false
+}
+
 #[cfg(target_os = "windows")]
 pub fn run_elevated_provisioning_setup(codex_home: &Path, real_user: &str) -> anyhow::Result<()> {
     codex_windows_sandbox::run_elevated_provisioning_setup(codex_home, real_user)
@@ -307,7 +342,13 @@ async fn run_windows_sandbox_setup_and_persist(
     let setup_result = tokio::task::spawn_blocking(move || -> anyhow::Result<()> {
         match mode {
             WindowsSandboxSetupMode::Elevated => {
-                if !sandbox_setup_is_complete(setup_codex_home.as_path()) {
+                if !elevated_setup_is_ready(
+                    &permission_profile,
+                    workspace_roots.as_slice(),
+                    command_cwd.as_path(),
+                    &env_map,
+                    setup_codex_home.as_path(),
+                ) {
                     run_elevated_setup(
                         &permission_profile,
                         workspace_roots.as_slice(),
diff --git a/codex-rs/tui/src/app/event_dispatch.rs b/codex-rs/tui/src/app/event_dispatch.rs
index 16e4aaa627..2777f7790c 100644
--- a/codex-rs/tui/src/app/event_dispatch.rs
+++ b/codex-rs/tui/src/app/event_dispatch.rs
@@ -1029,9 +1029,15 @@ impl App {
                     let codex_home = self.config.codex_home.clone();
                     let tx = self.app_event_tx.clone();
 
-                    // If the elevated setup already ran on this machine, don't prompt for
-                    // elevation again - just flip the config to use the elevated path.
-                    if crate::windows_sandbox::sandbox_setup_is_complete(codex_home.as_path()) {
+                    // Skip the UAC path only when the existing setup still refreshes cleanly
+                    // for the current workspace roots and permission profile.
+                    if crate::windows_sandbox::elevated_setup_is_ready(
+                        &permission_profile,
+                        workspace_roots.as_slice(),
+                        command_cwd.as_path(),
+                        &env_map,
+                        codex_home.as_path(),
+                    ) {
                         tx.send(AppEvent::EnableWindowsSandboxForAgentMode {
                             preset,
                             mode: WindowsSandboxEnableMode::Elevated,
diff --git a/codex-rs/tui/src/chatwidget/permission_popups.rs b/codex-rs/tui/src/chatwidget/permission_popups.rs
index 1283a9e490..1ed4532680 100644
--- a/codex-rs/tui/src/chatwidget/permission_popups.rs
+++ b/codex-rs/tui/src/chatwidget/permission_popups.rs
@@ -328,7 +328,13 @@ impl ChatWidget {
                     == WindowsSandboxLevel::Disabled
                 {
                     let preset = preset.clone();
-                    if crate::windows_sandbox::sandbox_setup_is_complete(
+                    let env_map: std::collections::HashMap<String, String> =
+                        std::env::vars().collect();
+                    if crate::windows_sandbox::elevated_setup_is_ready(
+                        &self.config.permissions.effective_permission_profile(),
+                        self.config.effective_workspace_roots().as_slice(),
+                        self.config.cwd.as_path(),
+                        &env_map,
                         self.config.codex_home.as_path(),
                     ) {
                         return vec![Box::new(move |tx| {
diff --git a/codex-rs/tui/src/windows_sandbox.rs b/codex-rs/tui/src/windows_sandbox.rs
index ec586e7b1b..b38f2d670b 100644
--- a/codex-rs/tui/src/windows_sandbox.rs
+++ b/codex-rs/tui/src/windows_sandbox.rs
@@ -42,6 +42,41 @@ pub(crate) fn sandbox_setup_is_complete(_codex_home: &Path) -> bool {
     false
 }
 
+#[cfg(target_os = "windows")]
+pub(crate) fn elevated_setup_is_ready(
+    permission_profile: &PermissionProfile,
+    workspace_roots: &[AbsolutePathBuf],
+    command_cwd: &Path,
+    env_map: &HashMap<String, String>,
+    codex_home: &Path,
+) -> bool {
+    if !sandbox_setup_is_complete(codex_home) {
+        return false;
+    }
+
+    codex_windows_sandbox::run_setup_refresh_with_extra_read_roots(
+        permission_profile,
+        workspace_roots,
+        command_cwd,
+        env_map,
+        codex_home,
+        Vec::new(),
+        /*proxy_enforced*/ false,
+    )
+    .is_ok()
+}
+
+#[cfg(not(target_os = "windows"))]
+pub(crate) fn elevated_setup_is_ready(
+    _permission_profile: &PermissionProfile,
+    _workspace_roots: &[AbsolutePathBuf],
+    _command_cwd: &Path,
+    _env_map: &HashMap<String, String>,
+    _codex_home: &Path,
+) -> bool {
+    false
+}
+
 #[cfg(target_os = "windows")]
 pub(crate) fn run_elevated_setup(
     permission_profile: &PermissionProfile,