Your program will have to detect when the dialog becomes obscured and re-raise it. Marking the dialog as a transient window is a request that the WM keep it above its "parent" but you are using override-redirect to exclude the dialog from the WM's management entirely.
In reply to Re: Tk overrideredirect topwindow on top
by jcb
in thread Tk overrideredirect topwindow on top
by Anonymous Monk
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