If "web development" isn't the right place, I apologize. I figured it was the best place to find people who have dealt with this... I'm setting up some internal stuff at work--a wiki and some blog stuff--but I'm having a heck of a time getting an SMTP server up and running on Windows Server 2003, probably because I don't know a thing about SMTP. A couple of questions: 1) What the heck is an IIS "SMTP Virtual Server"? It's running and is being used by a .NET app running in IIS, but my MediaWiki installation--which is running in Apache on port 82--can't see it. Is it truly "virtual" and only visible to inside of IIS? I can't even telnet to port 25. Why can't they just make an SMTP server that is actually usable? 2) I installed hMailServer, which seems nice, but it refuses to send anything. Every email results in a "550 Delivery is not allowed to this address" message. Any ideas how I can get this working?l

You can only have one mail server running on port 25 - choose one and stick to it.

Most MTAs don't allow relaying by default - not even from localhost, most of them. Normally you want to allow relaying from localhost - so you need to add that to their configuration.

IIS SMTP server can relay but only allows IP addresses you've allowed relaying from. See their docs for more info.

Mark

I had hMailServer set to some arbitrarily high port number, like 40000, so it wasn't a conflict. And the IIS SMTP server had localhost on the relay settings already.

Is there anything else you can think of that would cause those problems?

Thanks for responding.