There is a known issue in which a properly configured and authenticated version of Microsoft 365 Outlook for Mac displays a licensing error when attempting to connect to a Booth Microsoft 365 email account.
If this error is experienced, the following process will fix the error. This also applies to installation of the Mac App Store version. The App Store version cannot be activated though the Booth Microsoft 365 subscription and will not allow connection.
If you have already installed the App Store version, log out of Outlook and completely close it.
- In a new/unauthenticated browser session, go to portal.office.com and login with your CNetID@uchicago.edu account.
- Once logged in, on the right hand side, select Install Apps > Microsoft 365 apps.
- Download and install apps.
- Open Word. In the menu bar, select Word.
- Select Activate Word (and all other Office apps).
- Open Outlook. In the menu bar, select Outlook.
- Select Legacy Mode. This will restart Outlook in Legacy Mode.
- Sign in with your @ChicagoBooth.edu email address.
- You can either continue in Legacy Mode, or go back to the Outlook tab and return to New Mode.