troubleshooting Question

Exchange Hybrid - Possible send connector or SSL Problem

Avatar of Jeff Brubaker
Jeff Brubaker asked on
ExchangeMicrosoft 365* Exchange Hybrid
9 Comments1 Solution24 ViewsLast Modified:
I have single, Exchange 2013 server running in Full Hybrid Mode.
There are no on-premise mailboxes

Today, mail stopped flowing and I realized the SSL Cert had expired. (Woops!)

I quickly renewed the SSL Certificate and mail started working again immediately.

However, our phone voicemail system to email is not working. Tried rebooting the voicemail system and still no luck.

I'm wondering if it has to do with the "outbound to office 365" send connector. The reason I am suspicious is when I go to delete the expired SSL Cert from Exchange ECP, I get an error message "
A special Rpc error occurs on server EXCHANGE: These certificates are tagged with following Send Connectors : Outbound to Office 365. Removing and replacing certificates from Send Connector would break the mail flow. If you still want to proceed then replace or remove these certificates from Send Connector and then try this command.

But, if the expired SSL Cert is still tied to that send connector, how is my other email flowing ok?
If I do a Get-SendConnector "outbound to office 365" | fl  It just returns the basic information, not the thumbprint so I can't tell if it's the expired cert or not.

Any suggestions?

Ben County
It eng

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