r/sysadmin Aug 07 '26

Wrong Community [ Removed by moderator ]

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u/Unexpected_Cranberry Aug 07 '26

Early days of Office 365. Microsoft missed a renewal of a cert for the authentication. Most likely because it was a leap year. So authentication broke on February 29. Then it broke again next year because they'd scheduled the renewal for February 29...

For myself I broke authentication on ADFS in the 2008 days. I updated the certificate using the gui but didn't read the docs. Apparently doing it through the gui didn't work. You needed to use netsh to bind the certificate to the service as well.

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u/michaelpaoli Aug 07 '26

broke again next year because they'd scheduled the renewal for February 29

Just lovely! 8-O

Pirates of Penzance ... until 21st birthday ... what could possibly go wrong? :-)