Due to a problem in the Quartus® Prime Pro Edition Software version 19.2 and earlier, you may need to click OK button multiple times to close the dialog after programming file generation in the Programming File Generator.
This problem occurs when you repeatedly generate programming files without closing the Programming File Generator window. When you click the Generate button the first time, you can close the dialog by clicking the OK button once. But when you click the Generate button again, you need to click the OK button twice to close the dialog. When you click the 3rd Generate button, you need to click the OK button three times to close the dialog.
This problem has been fixed in the Quartus® Prime Pro edition software version 19.4 and later.