Totally stupid and probably not the issue; But instead of using a local script in the close button use a server script so that the server knows its not enabled aswell.
I believe this is because you’re closing the UI with a LocalScript but opening it with Server Script. When you close it, the server won’t know it’s actually closed. Therefore, the Enabled value won’t actually change to true on the server as it thinks it’s still true.
I’d recommend either making the .MouseButton1Click to close this on the server as well, or alternatively convert the server script to a local script.