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I think this is a subject that has been covered quite extensively, but I can't seem to the resolve the issues under my own steam.

I have a website that needs to be able to send emails out; it's hosted on a dedicated 2008 R2 Web Edition server. I've followed the instructions on the below website, with exception of the telnet test at the end.

http://www.itsolutionskb.com/2008/11/installing-and-configuring-windows-server-2008-smtp-server/

I've not fulfilled the telnet part of the tutorial, because every time I type in telnet localhost 25 into a command prompt, it pauses the reverts to a C: prompt.

I've been dropping emails into the Pickup folder in order to test whether system works or not. When I drop an email into the Pickup folder, it's instantly moved into the Queue folder, where it just sits. I'm unable to delete the emails as they're marked as in use.

The logs aren't saying much, that I can understand anyway.

#Fields: time c-ip cs-method cs-uri-stem sc-status
12:35:37 ... - - 0
12:35:37 ... EHLO - 0
12:35:37 ... - - 0
12:35:37 ... MAIL - 0
12:35:37 ... - - 0
12:35:37 ... RCPT - 0
12:35:37 ... - - 0
12:35:37 ... DATA - 0
12:35:37 ... - - 0

I've not done anything with DNS settings or anything like that. I've been given the impression that that is not necessary.

I've tested with and without Firewall activated.

Rich

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2 Answers

up vote 1 down vote accepted

Make sure you are using telnet app and the proper syntax should be "c webserver.com 25" Double check your SMTP service is running, and make sure "localhost' is checked in IIS for your website. Also make sure SMTP server is running in IIS, and that your send (All Except) and receives 127.0.0.1 are set...

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I can telnet to remote servers, but not to localhost. Both the SMTP service and the Virtual SMTP Server is running. I didn't follow want you meant in you last sentence, would you elaborate? –  kim3er Feb 23 '11 at 22:40
    
I've managed to successfully send an email from telnet using the server's remote address instead of localhost or 127.0.01. Will no test from a website. –  kim3er Feb 23 '11 at 23:11
    
Website test worked. Thanks for your help. –  kim3er Feb 24 '11 at 0:24
    
sorry for the delayed response, glad you got it working! –  Seth Feb 24 '11 at 14:10
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kim3er, btw you want to make sure that the SMTP service is binding to the correct IP, looking for SMTP connections. Usualy you can set to listen on the loopback (127.0.0.1) IP or the actual IP. This could be why you were not able to do a telnet session test.

Also if you feel the SMTP logs are a sparse, do note you can change that. By default it has the W3C format selected but with only very basic log fields. You can edit/add more or what I just prefer to do is switch to the NCSA log format.

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