Q: I've received a certificate error when opening Outlook on my Mac. What do I do?

• After updating certificates, Mac users running Outlook 2016 or newer might encounter a pop up error message stating "web.mit.edu certificate name does not match input"

Context

• This error typically occurs upon first launch of Outlook after certificates have been installed or updated using CertAid
• This error should only occur on MacOS 15.9 or higher

Cause

• This issue occurs in Outlook 2016 version 15.9 (or higher) for Mac, when Outlook performs an Autodiscover operation and tries to connect to a service endpoint whose expected name is not present on the server's Secure Sockets Layer (SSL) certificate.

Resolution

• The easiest resolution is to select the "Always trust web.mit.edu when connecting to mit.edu" checkbox and click the "continue" button.
• There is a manual resolution available which can be followed directly through Microsoft's documentation here