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I'm having a problem setting up IIS 6's SMTP service. I configured it with the options that made the most sense to me (I have zero IIS experience) and no mail is being sent. I telnetted into the server from its own command prompt, queued a message for delivery, and nothing happened. I looked through the server logs and was unable to find anything.

I appreciate that this is a very vague, general question but I'm honestly not sure where to start. Are there any quick options I should take a look at first before moving to more advanced configuration issues?

TIA.

EDIT: Logs
This is the content of the logfile for the session:

2009-09-02 20:40:27 127.0.0.1 - SMTPSVC2 JACK 127.0.0.1 0 HELO - ++1270.0.0.1 501 0 27 18 0 SMTP - - - -
2009-09-02 20:40:31 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 HELO - +jack 250 0 44 9 0 SMTP - - - -
2009-09-02 20:40:39 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 helmail - +MAIL+FROM+benjy@vavictory09.org 500 0 32 47 0 SMTP - - - -
2009-09-02 20:40:47 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 MAIL - - 501 0 28 4 0 SMTP - - - -
2009-09-02 20:40:50 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 MAIL - - 501 0 0 9 0 SMTP - - - -
2009-09-02 20:40:50 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 MAIL - +FROM 501 0 35 9 0 SMTP - - - -
2009-09-02 20:40:52 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 MAIL - - 501 0 0 10 0 SMTP - - - -
2009-09-02 20:40:52 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 MAIL - +FROM+ 501 0 35 10 0 SMTP - - - -
2009-09-02 20:41:44 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 MAIL - +FROM:+benjy@vavictory09.org 250 0 46 32 0 SMTP - - - -
2009-09-02 20:41:49 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 RCPT - +TO:+benjy@vavictory09.org 250 0 34 30 0 SMTP - - - -
2009-09-02 20:41:52 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 DATA - JACKVjCRGryWtIIZS2T00000005@jack.vavictory09.org 250 0 133 16 2171 SMTP - - - -
2009-09-02 20:41:55 127.0.0.1 jack SMTPSVC2 JACK 127.0.0.1 0 QUIT - jack 240 92890 69 4 0 SMTP - - - -

EDIT: Telnet session
220 jack.vavictory09.org Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at Wed, 2 Sep 2009 17:15:02 -0400
HELO jack
250 jack.vavictory09.org Hello [127.0.0.1]
MAIL FROM: benjy@vavictory09.org
250 2.1.0 benjy@vavictory09.org....Sender OK
RCPT TO: benjy@vavictory09.org
250 2.1.5 benjy@vavictory09.org
DATA
354 Start mail input; end with <CRLF>.<CRLF>
test test test
.
250 2.6.0 <JACKRqf69aZbLAX3cf300000006@jack.vavictory09.org> Queued mail for delivery
quit
221 2.0.0 jack.vavictory09.org Service closing transmission channel


Connection to host lost.

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3 Answers 3

up vote 1 down vote accepted

Do you have logging set up for the SMTP site? If so, there has to be something in the log file from your telnet session.

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Logs above. Thanks. –  benjy Sep 2 '09 at 21:13
    
Ok, the first several lines failed due to syntax errors as evidenced by the SMTP return codes. Down at the bottom you actually get a good transaction and your message is accepted and queued for delivery. I suspect that the problem is you appear to be using 127.0.0.1, which is the loopback address. Check the ip address binding on the SMTP site and make sure it's using the server's valid ip address. –  joeqwerty Sep 2 '09 at 21:19
    
Also, is the email address you're sending to valid? Is the domain valid? Can the server resolve the MX record for the domain? Is the recipient domain internal or external? Does the server have internet access? –  joeqwerty Sep 2 '09 at 21:21

Where are you having problems? Can you telnet and spoof a email client? Example here If you cannot complete this please elaborate as to your problem.

What version of IIS are you running?

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IIS 6, I believe. My Telnet session is above. Thanks. –  benjy Sep 2 '09 at 21:15

Check the smart host setting; this one can trip people up as it's kinda buried in a config dialog. I can't recall exactly where right now, but a search for IIS 6 SMTP smart host should get you it.

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a smarthost is not required for the operation of the SMTP service in IIS. The IIS SMTP service is fully capable of sending email on it's own. –  joeqwerty Sep 2 '09 at 23:51

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