Exchange 2010 Hub Transport Issues

I have two virtual Exhange 2010 SP1 Boxes (1 Mailbox and one Client access and Hub Transport server)

The Hub Transport seems to have some difficulty sending to only some email addresses failing with the following error:

"451 4.4.0 Primary Target IP address responded With: "421 4.2.1 Unable to Connect." Attempted to failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts."

Other errors are:
"451 4.4.0 Primary Target IP address responded With: "421 4.4.2 Connection dropped due to SocketError." Attempted to failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts."


Other emails seem to hit the queue and are sent by the time i can hit refresh.

any Ideasa on what going on?
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speeDemonAsked:
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speeDemonConnect With a Mentor Author Commented:
issue was with our Cisco ASA 5510 Firewall and ESMTP Packet Inspection... Once corrected, i was able to send email without issue
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Glen KnightCommented:
This is mail going out of your network yes?

Under Server Configuration right click on the server and select properties, under External DNS lookups, add your ISP DNS servers in here.

Then under Organisation Configuration > Hub Transport, check the properties of your internet send connector under Network check the box to use External DNS lookup settings.

Restart the Microsoft Exchange Transport service
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speeDemonAuthor Commented:
UI already had the check box for "Use External DNS" set so I added the IP I have for a known good DNS server and restarted the transport service and still no luck still getting the above error in the queue.

Here is what the logs are saying::

<,220 *******************,
>,EHLO my.mail.server,
<,250-a2s29.a2hosting.com Hello my.mail.server [<my RDNS IP],
<,250-SIZE 52428800,
<,250-PIPELINING,
<,250-AUTH PLAIN LOGIN,
<,250-XXXXXXXA,
<,250 XXXB,
*,27189,sending message
>,MAIL FROM:<sender@my.mail.server> SIZE=165387,
>,RCPT TO:<Rcpt@their.mail.server.org>,
<,250 OK,
<,250 Accepted,
>,DATA,
<,"354 Enter message, ending with ""."" on a line by itself",
<,421 magnus.websitewelcome.com SMTP incoming data timeout - closing connection.,
>,QUIT,
-,,Remote

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*Note: names have been changed for security
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speeDemonAuthor Commented:
My Own troubleshooting after members stopped posting suggestions
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captbackfireCommented:
What did you do to correct the issue with the ASA5510?
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