Exchange 2010 - Issue with send connectors?

In the middle of an Exchange 2010 to 2010 migration and was testing mail flow. I had both servers listed under 'Source Server' in Organization Configuration, Hub Transport, Send Connectors.

I moved a user to the new server, then removed the old server from the Source Server list and sent a couple of test messages outside. I see emails queuing up on the old server. I was under the impression the source server was the server that would send out the emails...especially for a user that was on that server and database. Am I not understanding this correctly?

I have updated my firewall to use the IP of the new server for one-to-one NAT so PTR records match, etc.
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mvalpredaAsked:
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Will SzymkowskiSenior Solution ArchitectCommented:
Are you getting any error messages beside the queued email? Or are they just sitting there?

Will.
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mvalpredaAuthor Commented:
Just sitting in queue.
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Will SzymkowskiSenior Solution ArchitectCommented:
Are you using a smart host in your DMZ or Edge server? If so can you telnet to the smart host from the new Exchange server?

Can you receive email from the internet?

Will.
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mvalpredaAuthor Commented:
451 5.7.3 Cannot achieve Exchange Server authentication." Attempted failover to alternate host , but that did not succeed. Either there are no alternative hosts, or delivery failed to all alternative hosts.

I have an internal relay connector set up, and have the old Exchange server listed in there. I just removed it. Made sure the 'Default' receive connector has 'Exchange Server authentication' ticked.
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Amit KumarCommented:
Please check event viewer and see if there any error. and how your Send connector is working. like sending mail to smart host or edge server?
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mvalpredaAuthor Commented:
Derp....my fault. I had another connector set up with the IP of the old Exchange server. It tried to use that connector since it was explicitly defined. Once I removed that mail flowed and out the correct send connector, IP, etc.

Would love to delete this question! ;-) I'm sure someone else will do something boneheaded like this, give them something else to check.
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Will SzymkowskiSenior Solution ArchitectCommented:
You need to make sure that Exchange Server Authentication is checked off. Once you have done that it should work for you. Check the authentication Tab.

Will.
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