diff --git a/bin/omarchy-sudo-passwordless-toggle b/bin/omarchy-sudo-passwordless-toggle
index a8857aa5..9757767b 100755
--- a/bin/omarchy-sudo-passwordless-toggle
+++ b/bin/omarchy-sudo-passwordless-toggle
@@ -7,6 +7,11 @@
 NOPASSWD_FILE="/etc/sudoers.d/99-omarchy-nopasswd-${USER}"
 TIMER_NAME="omarchy-nopasswd-expire-${USER}"
 
+# Safety: if the file exists but the timer doesn't (e.g. after reboot), clean up
+if sudo test -f "$NOPASSWD_FILE" && ! systemctl is-active "${TIMER_NAME}.timer" &>/dev/null; then
+  sudo rm "$NOPASSWD_FILE"
+fi
+
 # Check for the file directly — sudo -n can stay cached or be granted by other rules
 if sudo test -f "$NOPASSWD_FILE"; then
   sudo rm "$NOPASSWD_FILE"