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I'm currently using outlook 2019 on a windows 2012 server r2. Outlook constantly prompts for password. It does not matter if I enter it or not, my account is still logged in and it will still prompt for the password. Users on outlook 2013 do not have this issue and most of the users on Outlook 2019 also do not have the same issue. Only a few users on outlook 2019 have this issue. When we first set up our emails, it auto discovers so we don't have to enter any information.
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