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Exchange 2010 Hub Transport Issues

Posted on 2011-03-09
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Last Modified: 2012-11-26
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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Question by:speeDemon
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Expert Comment

by:Glen Knight
ID: 35088509
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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Author Comment

by:speeDemon
ID: 35100897
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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Accepted Solution

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speeDemon earned 0 total points
ID: 35485629
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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Author Closing Comment

by:speeDemon
ID: 35510860
My Own troubleshooting after members stopped posting suggestions
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Expert Comment

by:captbackfire
ID: 38634381
What did you do to correct the issue with the ASA5510?
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