Exchange outbound issues

We recently switched moved our exchange environment from a physical box to a vm and upgraded to Exchange 2010 SP3. Following the upgrade and server move we are now unable to send to certain domains. We did not change the DNS record as we simply were going to change the NAT in our asa to point to the new server. We are using office365 as our spam filter and those settings appear to be correct as well. When users send to the affected domains they recieve :

Delivery is delayed to these recipients or groups:
Mike ******* (mike@*************.com)
This message hasn't been delivered yet. Delivery will continue to be attempted.
The server will keep trying to deliver this message for the next 1 days, 19 hours and 52 minutes. You'll be notified if the message can't be delivered by that time.
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Simon Butler (Sembee)ConsultantCommented:
That is just a delay message. It doesn't really tell you very much.
You need to look in the queue viewer to see what the real problem is.

Did you change the FQDN on the Send Connector to match the PTR on your external IP address? If not then that could cause some delays.

In the ASA do you have the fixup SMTP feature disabled (or whatever Cisco call it now).

homesgAuthor Commented:
I pointed the NAT on the asa to point back to the old exchange server and all the mail left the queue.  For some reason all internal mail wants to route through our old exchange not the new one even though all our outlook clients are pointed to the new server.  On the send connector under the source Server tab I have both exchange servers listed.  Should I remove the old one to correct this issue?
Simon Butler (Sembee)ConsultantCommented:
If you have both servers listed in the connector, then Exchange will use both servers.
If you only want one server to send email, then remove the other.
Where the clients connector to makes no difference.

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homesgAuthor Commented:
I removed the old server from the send connector and mail is still getting stuck in the queue's on the old server.  Not all mail, I guess its trying to load balance some mail will go out if the new server.  Is there something else that is telling these servers to work together?
Simon Butler (Sembee)ConsultantCommented:
Exchange will attempt to route email to the new server via the old server. You cannot stop that behaviour until you remove the server.

If you are seeing messages stuck on the old server in the queue, then you need to look at the reason why. The usual cause is that the Default Receive Connector has been modified away from the default - for example changes to the authentication settings or a restriction placed on the connecting IP address range.


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homesgAuthor Commented:
Had set the send connector and restart the transport service on both boxes in order for outbound mail to work correctly.
homesgAuthor Commented:
I figured out I needed to reboot the transport service.
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