We have an Exchange 2010 Hybrid with Office 365. We have multiple domains. I used the Hybrid Deployment Wizard to set this all up and everything is operational until I attempted to add a new domain. I created the domain completely on the O365 side (New Domain, configured all of the DNS to O365, etc). On-Premise, I added the accepted Domains, the UPN for ADUC, etc. For users that have their mailbox already on EO, mail is able to get to the new domain. Any External emails are received. However, any emails sent from an on-premise Mailbox, fails to be delivered. Checking the message tracking details, the messages seem to get into a infinite loop (LoopDetected). In reviewing the details, the message is using the wrong SMTP Connector when sending to that domain. If I send from on-premise to EO, the connector used is Outbound to Office 365, the connector created by the wizard. When use with this domain, it uses the original SMTP (called New SMTP Server) that is used for all other mail traffic.
[PS] C:\Windows\system32>get-sendconnector
-------- ------------- -------
New SMTP Server {SMTP:*;3} True
Outbound to Office 365 {smtp:[ourdomainname].mail.onmicroso... ;1} True
The new domain has been added to the Accepted Domain list on both On-Premise and on EO. On-premise, I had the domain type as Authoritative, but I changed it to InternalRelay and that has not solve the issue.
Any help?
New users were created both in the cloud and on-Premise (tried both ways). It seems it is recommended that new user accounts should be created locally with their mailbox then migrated, so that the GUID is added for Exchange. I created two separate distribution groups (both under EOP) and the same scenario occurs.
There is no doubt by the logs, the message never goes out bound. We have an IronPort device that all messages go out to through the New SMTP Server connector. In the log, I can see the message going out to that smarthost and then back in then out and back in (the loop). Not sure why that traffic is not going out through the Outbound to Office 365 Connector like all other domains. Even went back and ran the Hybrid Wizard again with no success. I have a trouble ticket in with MS and they have not been able to determine the issue as of yet.
Please help. :)