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Troubleshoot SMTP send from Exchange

Posted on 2011-02-15
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Last Modified: 2012-05-11
I've got a user that when she sends an email to a specific external recipient, her message gets delayed and ultimatly never gets delivered.  I'm gettign a 4.4.7 error on my side.

So, I did a telnet to the remote domains server on port 25. Then did teh following:
220 remotedomain.com ESMTP
mail from:User@mydomain.com
250 ok
rcpt to:recipient@remotedomain.com
250 ok
test
502 unimplemented (#5.5.1)

502 unimplemented (#5.5.1)

502 unimplemented (#5.5.1)
502 unimplemented (#5.5.1)
502 unimplemented (#5.5.1)

What would the cause of a 5.5.1 be?
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Question by:JamesonJendreas
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Expert Comment

by:connectex
ID: 34900491
The 502 is correct as you haven't followed the proper process for testing. The next command is DATA. See this: http://technet.microsoft.com/en-us/library/aa995718(EXCHG.65).aspx
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Author Comment

by:JamesonJendreas
ID: 34901557
duh, I know better than that....
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Expert Comment

by:connectex
ID: 34901577
Ok. So now you should be able to get some more information to aid in troubleshooting this issue.
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Author Comment

by:JamesonJendreas
ID: 34901643
Hmm, here's my output, looks ok to me:

220 remotedomain.com ESMTP
mail from:afogerson@mydomain.com
250 ok
rcpt to:tonyb@remotedomain.com
250 ok
data
354 go ahead
test
.250 ok 1297807893 qp 14046 by apspackaging.com
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Accepted Solution

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connectex earned 500 total points
ID: 34901668
The 250 ok line means they accepted the test message. So it's not a basic connectivity issue. The only other idea is it's not liking the content of the messages previously. But that's entirely upto the user sending them.
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