diff --git a/.bin/Scripts/functions/diags.py b/.bin/Scripts/functions/diags.py
index f66d59e0..54c4105d 100644
--- a/.bin/Scripts/functions/diags.py
+++ b/.bin/Scripts/functions/diags.py
@@ -38,7 +38,7 @@ def check_connection():
             else:
                 abort()
 
-def check_secure_boot_status():
+def check_secure_boot_status(show_alert=False):
     """Checks UEFI Secure Boot status via PowerShell."""
     boot_mode = get_boot_mode()
     cmd = ['PowerShell', '-Command', 'Confirm-SecureBootUEFI']
@@ -51,18 +51,30 @@ def check_secure_boot_status():
             # It's on, do nothing
             return
         elif 'False' in out:
+            if show_alert:
+                show_alert_box('Secure Boot DISABLED')
             raise SecureBootDisabledError
         else:
+            if show_alert:
+                show_alert_box('Secure Boot status UNKNOWN')
             raise SecureBootUnknownError
     else:
         if boot_mode != 'UEFI':
+            if (show_alert and
+                global_vars['OS']['Version'] in ('8', '8.1', '10')):
+                # OS supports Secure Boot
+                show_alert_box('Secure Boot DISABLED\n\nOS installed LEGACY')
             raise OSInstalledLegacyError
         else:
             # Check error message
             err = result.stderr.decode()
             if 'Cmdlet not supported' in err:
+                if show_alert:
+                    show_alert_box('Secure Boot UNAVAILABLE?')
                 raise SecureBootNotAvailError
             else:
+                if show_alert:
+                    show_alert_box('Secure Boot ERROR')
                 raise GenericError
 
 def get_boot_mode():
@@ -170,5 +182,10 @@ def run_rkill():
                 dest = non_clobber_rename(dest)
                 shutil.move(item.path, dest)
 
+def show_alert_box(message, title='Wizard Kit Warning'):
+    """Show Windows alert box with message."""
+    message_box = ctypes.windll.user32.MessageBoxW
+    message_box(None, message, title, 0x00001030)
+
 if __name__ == '__main__':
     print("This file is not meant to be called directly.")