Hi all,
Recently i changed jobs and walked in to a company with a hybrid Exchange configuration. Office 365 and 2 onprem exchange servers. one is Exchange 2010 and one is Exchange 2013.
We only use the internal exchange servers for internal relay and by the looks of it. the send connectors on our Exchange 2013 is going via the Exchange 2010 and then the send and receive connectors between on-premise and Office 365 go via Exchange 2010.
These are our receive connectors
Identity Bindings Enabled
-------- -------- -------
XXXSRVEX3\Main Servers Relay {0.0.0.0:25} True
XXXSRVEX3\Client UPPSRVEX3 {[::]:587, 0.0.0.0:587} True
XXXSRVEX3\Default UPPSRVEX3 {[::]:25, 0.0.0.0:25} True
XXXSRVEX3\Inbound from Office 365 {0.0.0.0:25} True
XXXSRVEX365\Default UPPSRVEX365 {0.0.0.0:2525, [::]:2525} True
XXXSRVEX365\Client Proxy UPPSRVEX365 {[::]:465, 0.0.0.0:465} True
XXXSRVEX365\Default Frontend UPPSRVE... {[::]:25, 0.0.0.0:25} True
XXXSRVEX365\Outbound Proxy Frontend ... {[::]:717, 0.0.0.0:717} True
XXXSRVEX365\Client Frontend UPPSRVEX365 {[::]:587, 0.0.0.0:587} True
XXXSRVEX365\Internal servers relay {0.0.0.0:25} True
I am not sure which if any we can disable so they are all true. what we have done though is we set up 2 internal relay connectors for internal devices and applications that relay through them.
several times a day we can see on the queue viewer on the Exchange 2013 host the below error. Restarting the transport service on the Exchange 2010 server does not work. it times out and then we tend to just reboot the server.
"Next Hop Domain""Delivery Type"Status"Message Count""Next Retry Time""Last Error"
"outbound to office 365""SMTP Relay to Send Connector Source Servers"Retry1"24 July 2018 12:03:06""[{LRT=24/07/2018 12:02:05};{LED=441 4.4.1 Error encountered while communicating with primary target IP address: ""Failed to connect. Winsock error code: 10061, Win32
error code: 10061."" Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts. The last endpoint attempted was 10.90.2.87:25};{FQDN=outbound to office 365};{IP=10.90.2.87}]"
"send all out though 365""SMTP Relay to Send Connector Source Servers"Retry750"24 July 2018 12:05:57""[{LRT=24/07/2018 12:00:57};{LED=441 4.4.1 Error encountered while communicating with primary target IP address: ""Failed to connect. Winsock error code: 10061, Win32
error code: 10061."" Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts. The last endpoint attempted was 10.90.2.87:25};{FQDN=send all out though 365};{IP=10.90.2.87}]"
SubmissionUndefinedReady0
xxxsrvex3.xxx-ltd.local"Shadow Redundancy"Ready2
But i have also seen issues from Office 365 reporting STARTTLS command could not be sent to the Exchange 2010 server which i am unsure how to troubleshoot. One thing i did see is that there is no self signed cert on Exchange 2010 for the hostname of the
server. but we have got a wildcard *.company.com on it.
I have a gut feeling these things are all connected
If anyone could help it would be highly appreciated.
Best regards
Ronnie