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When accessing Outlook or some websites (including Single Sign On (SSO) Resources using Safari for Mac OS) from a MacOS, you may be prompted for a Certificate Error.  See image below: 

This is a known issue between Apple and many university authentication systems.This happens because the default keychain will not trust Fairfield University's sign-in (authentication) page.can happen for any website or server whose certificate is expired, for security reasons Apple can not automatically trust them. In Outlook or Safari you can "trust" the certificate and won't be prompted again. For non-University websites be sure it is a site you are certain about before trusting.

See image below:


  1. When prompted with this a Certificate error. Click Show Certificate
  2. Click the checkbox for Always trust "*" when connecting to "" " (or the lowest line item with a red "X"). Then click Continue

  3. You will then be prompted for your computer password. Enter it, then click Update Settings.
    You will be brought to the Single Sign On page correctly. Enter your NetID and Password. Enter your only your NetID and password.
    Image Removed
  4. You will no longer receive the Certificate Error in Safarifor that site.

For further assistance, please visit the ITS4U Help Desk located in NYS 215 or call 203-254-4069 during business hours.

Hours can be found here: ITS4U Help Desk Hours of Operation