Hi, @Chawon Hendricks
Looks like the issue is more related to Windows Server, please kindly understand that the Exchange Online tag here we mainly focus on general issues about Exchange Online.
Depending on your operation, when you use cntrl+atl+del to change the password, you are actually changing the password of the AD user, which usually has nothing to do with Outlook.
In order to provide you with a more professional answer, we will add Windows Server tag for you.
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