Basic Authentication Transition Guidance for Macintosh Systems Running Exchange Web Services Protocol
|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
- Navigate to Apple Menu > System Preferences > Internet Accounts
- Locate and remove Outlook/Exchange account
- 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
- Within Keychain Access you will be prompted with a list of saved accounts
- In the Search field within Keychain Access search for “Exchange”, select any entries found and then press the delete key
- Once all Exchange entries are deleted repeat step 5 with the keyword “Office”, select any entries found and then press the delete key
- Once all Office entries are deleted repeat step 5 once again with keyword “ADAL”, select any entries found and then press the delete key
- 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
- Reboot your Mac
- Once rebooted and signed back in, reconfigure your Outlook account by navigating to Apple > Menu > Preferences > Internet Accounts
- When prompted for account type select Exchange
- A new window will prompt for a name and email address. Enter your Name and UChicago email address, then click the Sign In button
- When prompted to “Sign in to your Exchange account using Microsoft?” click Sign In again
- When prompted to “Log in to Your UChicago Account”, log in with your CnetID and Cnet password. You should then be prompted for 2FA
- Once 2FA has been successfully established you will be prompted with a Permissions requested screen at that time, click Accept
- 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.