Emails stuck in the SMTP queue on Windows 2008 R2 Web Edition

Question

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

Solution

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...

Comments

[kim3er]

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]

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.

[Seth]

sorry for the delayed response, glad you got it working!