Outlook 2011 asking for password over and over

[kwoodvisions]

I have a user with a Mac tower running Mac OS X 10.7.5 that is domain-joined to our Windows network. We recently upgraded to Office 365 and since the switch, this user is continuously prompted in Outlook 2011 for their password.

I cannot upgrade to Office 2016 because Office 2016 needs a newer version of Mac OS X. I cannot update Mac OS X as it tells me there are no further updates for the machine. The user refuses to give up the computer and insists that it is something I've done because, prior to the switch to Office 365 we had on-premise Exchange and everything worked fine and they were not being prompted for their password.

I have searched extensively online and have deleted Keychain entries, repaired Keychain (it said there were no errors every time), I have uninstalled Outlook 2011 and reinstalled it -- none of these have worked or fixed the issue.

As a work around, I've found that the issue must be between Outlook/Office 365 and Keychain because, if the user is prompted for their password, they say "No", then go to "Tools --> Accounts", type in their password and close the Accounts window and the email will sync and connect to Exchange. Maybe it's Keychain, maybe it's not..

At this point I'm not sure and am looking for any and all help I can get.

 

[Cory Cooper]

Hello and welcome.

-Which exact model Mac?
-Which version of Exchange Server?
-Do you have webmail setup?
-Do a Get Info on the Outlook 2011 app and check the box next to Prevent App Nap - if that option is available. (But, I think this feature was introduced with 10.9 Mavericks)

C