Outlook – O365 prompting for password in Outlook 2016 constantly, won’t take log in info but is still able to send and receive email

I have an Office 365 account set up with two email accounts under one profile in Mail 32 in control panel.

Every time Outlook 2016 is open it prompts for just one of the accounts passwords, I enter the password in and it is just a never-ending loop.

I cancel that menu and I am able to send and receive email on both accounts. I left click on the "Need password icon" at the bottom right and I can clear the message and it will just say "Connected to Microsoft Exchange".

Additionally, that clears it or sending and receiving email. Seems like a false positive, and this is also a brand new set up. Lots of emails in both accounts, but these accounts are newly added to the Outlook. Is there any way around this?