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Cannot get outlook express to send eamil from remote site through exchange server

Posted on 2009-05-06
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Last Modified: 2013-11-30
We have an exchange 2003 server at a clients location behind a firewall.
SMTP, POP3, and IMAP ports are forward through firewall.
When the user from home tries to send an email through the server to an outside address we get

The message could nt be sent because one of the recipients was rejected by the server. The rejected e-mail addess was "outside address". Subjet 'test' Account: 'gary'. Server: "exhchange FQDN", Protocol: SMTP< Server response: "550 5.7.1 Unable to relay for "outside address", Port:25, Secure(SLL): No, Server Error; 550, Error number: 0x800CC79

If I allow relaying through the server for any computer this work, but I cannot have an open relay. I have "Allow all computers which successfully authenticate to relay" checked.

Anonymous, Basic and Integrated Auth. is checked for Authentication.

Need help.

Thanks
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Question by:DMooring
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6 Comments
 
LVL 33

Expert Comment

by:Dave Howe
ID: 24319598
the server setup is correct - what you are missing is actually getting the client to authenticate first. make sure that in outlook express account setup, "my sending smtp server requires authentication" is checked - it should then prompt for a user/pass with a tickbox to remember that info for future use.
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Author Comment

by:DMooring
ID: 24320015
I should have put that in my first post but smtp authentication is checked.
Is there someting I can log on the server to see what is happening.

I am getting this in the application event log.

Event ID 7010

This is an SMTP protocol log for virtual server ID 1, connection #1. The client at "208.34.224.2" sent a "rcpt" command, and the SMTP server responded with "550 5.7.1 Unable to relay for ?????@cocentral.com  ". The full command sent was "rcpt TO: <?????@cocentral.com>".  This will probably cause the connection to fail.
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LVL 33

Accepted Solution

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Dave Howe earned 500 total points
ID: 24320811
not if tls is also in play. otherwise, you can use something called "trivial proxy" to log the full exchange at the client side, and see what is going on.

http://www.xrayapp.com/trivialproxy/

I have used it to debug many protocol issues :)
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Author Comment

by:DMooring
ID: 24327116
Ran trivialproxy. This is the results.

220 ********************************************************0****0***************************200******0*****0*00
EHLO djones
500 5.3.3 Unrecognized command
HELO djones
250 mail.fwbch.org Hello [208.34.224.2]
MAIL FROM: <user@fwbch.org>
250 2.1.0 user@fwbch.org....Sender OK
RCPT TO: <user@cocentral.com>
550 5.7.1 Unable to relay for user@cocentral.com
QUIT
221 2.0.0 mail.fwbch.org Service closing transmission channel

Researching the 500 5.3.3 Unrecognized command error I came across this Experts-Exchange
artical ID: 23147759. Ran the no fixup protocol smtp 25 command on the Cisco Pix and it works now.

Thanks

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LVL 33

Expert Comment

by:Dave Howe
ID: 24330475
heh yeah, had one of those today in my dayjob - 220 ******* is characteristic of fixup on a pix (or INSPECT ESMTP on an ASA or recent IOS router)
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Author Comment

by:DMooring
ID: 24330522
DaveHowe,
Thanks for all the help. This was my first post. I hope I closed it right and you got the points.
If not let me know.
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