1. You should see a pop-up like the one below appear. Make note of the URL, as it contains “mail.onmicrosoft.com”, as opposed to the exchange.uic.edu settings pop-ups that might have appeared in the past.
2. Check the “Always use my response for this server” and click Allow. Let Outlook sync on its own or click Send/Receive to manually start.
3. Outlook will ask for your password again. Feel free to add this to your keychain.