Windows – Hybrid on-prem connector – Won’t validate – Backlog of emails

exchangewindows

We're having an issue with our on-prem Exchange 2016 validating as a connector with our O365 portal, below error;

450 4.4.316 Connection refused [Message=Socket error code 10061] [LastAttemptedServerName=hybrid.X.com] [LastAttemptedIP=X.X.X.X:25] [X.eop-eur04.prod.protection.outlook.com]

I believe this is something to do with the SMTP port itself but I'm not all that savvy with the infrastructure yet. Is there anything obvious to look out for? We have a backlog of 2500 emails waiting to go but it appears this is causing the issue.

Best Answer

Did you get any error message when you run HCW?

According to the error message, yes, a likely cause for this error is your firewall is blocking connections from Office 365 IP addresses.

If you have mailboxes in your on-premises environment, you need to modify your firewall settings to allow connections from Office 365 IP addresses on TCP port 25 to your on-premises email servers. For a list of the Office 365 IP addresses, see Office 365 URLs and IP address ranges.

Similar thread: https://social.technet.microsoft.com/Forums/en-US/ef63dcb2-b814-4638-964c-ef5fc75612df/message-delayed-with-450-44316-connection-refused?forum=onlineservicesexchange