I did a replace on an Exchange 2010 Edge server recently, and on this environment it was also a hybrid connection to Office 365. This is my findings.
So I did the usual stuff, installed Edge role on the new server. Implemented certificate. Because of firewall and such, we needed to re-use the IP of the old Edge server. But a new name according to naming conventions at the customer.
Therefore we run the Remove-EdgeSubcription. Then three Send connectors disappeared. The usual “EdgeSync” connectors, but also the Outbound to Office 365 that has been created by the Hybrid Wizard.
After I had implemented the new Edge server and the basics was in place, the routing between on-prem and O365 hybrid cloud was not working (because of the missing send-connector). The mail going to the hybrid SMTP routing domain (tenantname.mail.onmicrosoft.com) ended up in a “local loop was detected” error.
I thought that running the Update-HybridConfiguration would do the trick, and yes the Outbound To Office 365 was created. But I saw that the Get-HybridConfiguration was showing the wrong Edge server. The EdgeTransportServers showed the old Edge name. I updated that, then another error message showed up. It was complaining about the TlsCertificateName on the SendConnector on Edge server.
So then I updated the TLSCertificateName
$cert = Get-ExchangeCertificate –Thumbprint “thumbprint of EX certificate”
$TLSCert = (‘<I>’+$cert.issuer+'<S>’+$cert.subject)
Set-SendConnector -Identity “Outbound to Office 365” -TLSCertificateName $TLSCert
After a suspend and resume the mailflow started to work:)
(I guess I could re-runned the Exchange Hybrid Wizard as well, but what’s the fun in that? )