Client that has Outlook 2016 and one of his emails connects to Exchange 365 account. Something went around and everyone using the account had to re login with email address and password. For this client there would be a white box with nothing in it pop up for a few seconds and then disappear. I tried removing the account from Outlook and then re add it but it would still do the same thing.
Found this online
Basically I had to do this workaround by adding a registry entry:
The workaround that I’ve implemented is to turn Modern Authentication off for the clients that are experiencing the issue. I’ve done so by implementing the following registry key (DWORD (32-bit) Value) after closing Outlook:
HKCU\SOFTWARE\Microsoft\Office\16.0\Common\Identity\EnableADAL
Setting this key to 0 disables Modern Authentication within the Outlook client. No reboot is required. After opening Outlook back up, I was greeted with the basic authentication password prompt. After entering the user credentials and opting to have them remembered, the clients have remained connected.
Once I did this and opened Outlook it would work.
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