This was posted in Trainz Talk, so I'm posting a link to the original thread for everyone in General Trainz, where more people will see it. I wish I could post this in the TrainzDev or the TNI sections of the forums for those who have a better idea of scripting, as it sounds like a script problem.
Link: https://forums.auran.com/trainz/showthread.php?163453-Trouble-with-windows-update-KB5001330&p=1869343#post1869343
Link: https://forums.auran.com/trainz/showthread.php?163453-Trouble-with-windows-update-KB5001330&p=1869343#post1869343