Basic Authentication Transition Guidance for Macintosh Systems Running Exchange Web Services Protocol

This guide is for Macintosh users who run older versions of Outlook, or who setup their Apple Mail accounts using Basic Authentication some time in the past.  The systems use Exchange Web Services, which although capable of doing modern authentication may have been configured to using legacy Basic Authentication. For most Apple Mail users, the solution is to remove and re-add your UChicago email. Outlook users with valid UChicago credentials may  be able to install a new version of Outlook.  We invite SSD faculty and staff to contact our support.

Device Type Operating System Version Email Application
Mac 10.14 or later Apple Mail
Outlook 2019 for Mac (exchange only, no POP or IMAP)
Outlook for Mac – Office 365 (exchange only, no POP or IMAP)

Fix: If your mac is running MacOS 10.13 or earlier, please contact SSCS as your mac may require an upgrade. If your equipment eligible for upgrade we may need to assess next steps.

If your mac is running MacOS 10.14 or later, you may choose to resolve the problem yourself by following the instructions below or contacting SSCS for help.

Re-configuring MacOS Apple Mail for O365 Modern Authentication

  1. Navigate to Apple Menu > System Preferences > Internet Accounts
  2. Locate and remove Outlook/Exchange account
  3. Open Spotlight search in upper right corner (or press⌘ + spacebar on your keyboard) and do a search for an application called Keychain Access, open Keychain Access
  4. Within Keychain Access you will be prompted with a list of saved accounts
  5. In the Search field within Keychain Access search for “Exchange”, select any entries found and then press the delete key
  6. Once all Exchange entries are deleted repeat step 5 with the keyword “Office”, select any entries found and then press the delete key
  7. Once all Office entries are deleted repeat step 5 once again with keyword “ADAL”, select any entries found and then press the delete key
  8. Once all ADAL entries are deleted, repeat step 5 once again with the keyword “Xmail.uchicago.edu”, select any entries found and then press the delete key
  9. Reboot your Mac
  10. Once rebooted and signed back in, reconfigure your Outlook account by navigating to Apple > Menu > Preferences > Internet Accounts
  11. When prompted for account type select Exchange
  12. A new window will prompt for a name and email address. Enter your Name and UChicago email address, then click the Sign In button
  13. When prompted to “Sign in to your Exchange account using Microsoft?” click Sign In again
  14. When prompted to “Log in to Your UChicago Account”, log in with your CnetID and Cnet password. You should then be prompted for 2FA
  15. Once 2FA has been successfully established you will be prompted with a Permissions requested screen at that time, click Accept
  16. Once complete, Apple Mail should be configured and working with the newly released authentication method

Re-configuring Outlook 365 for O365 Modern Authentication


If you are using an older version of Outlook, update it to Outlook 365. You can find the installer for the latest version of Outlook 365 by logging into https://portal.office365.com/ with your uChicago credentials. If your operating system supports it, we recommend using the latest version of Outlook 365 as your default email program. Because it is by Microsoft, it works very well with the university’s Microsoft-hosted email system.

As an alternative, you can always access email via the web: https://outlook.office365.com/.

Please feel welcome to contact SSCS if you need help configuring your email.