Forum Discussion
One 365 mailbox and several non 365 mailboxes
This looks like a mail flow loop rather than a connector validation issue. The error 554 5.4.14 Hop count exceeded typically means mail is bouncing back and forth between Exchange Online and your external IMAP mail server.
A few things to check:
- MX Record & Routing
If your MX record points to Exchange Online, then O365 needs to know which users are hosted on IMAP vs. Exchange Online. For IMAP users, you’ll usually need a mail flow connector or smart host rule that routes their mail to your external server. - Accepted Domain Setting
Make sure your domain in Exchange Online is set as Internal Relay (not Authoritative). Authoritative tells O365 that all mailboxes are hosted there, which causes a loop when it can’t find the IMAP user. - Connectors
It sounds like you already created in/out connectors. Ensure the outbound connector from O365 → IMAP server is selected in your transport rules. - Command Confusion
You’re right: Start-Edge Synchronization applies only to on-premises Exchange servers. In Exchange Online, directory sync isn’t done this way. For your case, it’s purely a mail flow / accepted domain configuration issue, not an edge sync issue.
In short:
Set your domain in Exchange Online to Internal Relay.
Confirm your connector routes unknown recipients to your IMAP host.
Test delivery with Get-Message Trace in Exchange Online to see where it’s looping.
That usually resolves the loop in hybrid-style setups where some users are on O365 and others remain on IMAP.
Thank you for that clear explanation.
The MX records are correct
The domain setting is set to Internal relay
The two connectors are set up and the one from O365 to my organisation validates OK
When I try to set up a transport rule for the connector, it is not listed as available as a connector to route to.