I have an exchange 2010 server running on Windows 2008 R2, I also have a remote webserver running Windows 2003 with multiple sites on it (all asp.net mvc 2 sites). I setup a Transport in exchange and all the websites on my remote web server can send email no problem to anyone in the exchange server and to any external domain.
Now for my problem. I am having issues with that webserver, so I moved one of the websites to run on my exchange server, it runs well (low hit website) except that email doesn't work from that site. I tried changing the Transport in exchange to add the IP address of the local machine and the 127.0.0.1 addresses and it still isn't sending any email.
Any ideas on how to get this working?
The remote websites can still send email no problem, the version of the site that I had to move on the remote server can still email, but on the exchange server for that website email does not send.
I would guess it is a Transport issue, since it is running on the same server a firewall shouldn't be the issue.
I changed the smtp setting in web.config to localhost, and now I do receive email to my account on the exchange server, but I do not receive any emails on outside addresses.
To add more description, this is a custom developed asp.net mvc 2 website. And no errors were being generated in the code when sending the email in either case.
Best Answer
You need to give more details about your application. Are you trying to send authenticated email or anonymous email? Are all your websites that were running on Windows 2003 no longer working with the exchange mail server or is it just one specific site?
You might want to check out http://www.systemwebmail.com/default.aspx as they may have a programmable solution for you. I don't recommend running any kind of website on an exchange server regardless of how heavy or light the usage may be.
Some simple things to check: firewall ports, any updates/patches applied to the exchange server and/or web server that may affect ports, check logs on both the web/exchange server, etc. etc. It would probably be easier to step-through your web application in visual studio using breakpoints to see what exactly is going on in the application, but I would try first to diagnose whether this is an application problem vs. non-application problem.
Is this a custom ASP.NET application or a vendor solution? I think you need to read this page (http://www.systemwebmail.com/faq/4.1.aspx#4.1) and try to determine some of the factors contributing to this issue.