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My ancient mail server machine crapped out a few days ago. I cobbled together another machine from spare parts and the bone pile, which included reformatting the existing disk and installing a fresh copy of Windows 2000 (I've got lots of Win2000 licenses). This will be the internal SMTP server for the small company I work for.

The SMTP server for receiving mail for the domain, associated POP3 server, queuing system, and system that does some custom things including running scripts triggered by certain mail messages is our own software and does what we want. What I'm looking for is a means of sending mail to external addresses. This software needs to contact a DNS server, do the MX lookup, and send messages via SMTP to the various target systems. The internal interface to hand it mail messages can be just about anything, although most likely that will be via SMTP also. Free is fine, but I have no problem paying for such software if it does what I want without problems. However, any commercial software must have a trial period of at least 14 days because my experience is that there are a lot of gotchas and any software needs to be proven to work. If it works fine for 14 days I'm happy to pay for it.

I've tried a few free programs already, but each has its problems. One (don't remember the name) worked great but was limited to 10 messages/day although this was nowhere mentioned in the documentation. That really pissed me off, and I'd like to avoid that vendor. I wasn't entirely happy with the forwarding server in use before, so after 8 years or so it's time to look around again and hopefully find something better.

To summarize, here are the requirements:

  • Must run on Windows 2000.

  • Must NOT establish a server on ports 25 or 110, or must be configurable to avoid those ports.

  • Does not need security in accepting mail. It will be behind a router that will not expose its ports externally.

  • May be free or commercial. If not free, must have at least 14 day free evaluation period.

  • May use SMTP to receive mail to be forwarded, but may also require some alternate interface, like running a executable per message.

  • Does not need a queuing system, POP3 server, etc. Just needs to forward messages to MX machines of target domains.

Any suggestions?

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closed as off topic by Sam Jan 18 '12 at 21:15

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I'm posting this for a friend, so I may not be able to answer many of your questions regarding details beyond what is mentioned. – Adam Davis Feb 4 '10 at 17:52
Some questions (you may need to pass these on). Do you have AD? What do you do about backing up your email server? What server software did you use before? – 21st Century Moose Feb 13 '10 at 18:12

The Internet Information Server (IIS) software that ships with Windows Server includes a basic SMTP engine that will do what you're looking for. You can install this through the "Add/Remove Programs" section of the Control Panel. Go into the Windows Components, then into the details for IIS and find the SMTP Service.

Once installed, it can be configured to accept connections on any IP/port combination on the server. You can send messages through via SMTP or writing a MSG file to the pickup folder if desired. It will handle external delivery from there.

Of course you will need to also ensure that the usual e-mail rules are followed such as having a proper reverse DNS entry on the IP you're sending from, etc.

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Do you happen to know what limitations might exist on the Windows 2000 Professional IIS SMTP server? I can find information on the web server limitations for professional vs server editions, but I don't see a list of limitations for the SMTP server component. – Adam Davis Feb 5 '10 at 14:29
It's an SMTP server. What kind of limitations are you thinking about? – Trevoke Feb 5 '10 at 14:46
As Trevoke mentioned, it's just an SMTP delivery engine. There aren't any limitations in that respect. It doesn't have advanced options like delivery throttling for specific domains, DKIM message signing, etc. It just relays mail via SMTP, that's all. – Justin Scott Feb 19 '10 at 19:10

I have some comments about your requirements. The biggest one is any MTA (mail transfer agent -- which is what you're looking for) must have the ability to queue messages. What happens when the target domain's MX is down? Or returns a 400 error code? If your MTA doesn't queue the message to be retried later, what else is it going to do except drop the message on the floor? You should reject any software that can't queue.

Why don't you want it to listen on port 25? After all, that's the standard SMTP port. Especially since you'll be behind a firewall. That's more a matter of choice, though.

Don't reject other OSes out of hand. Linux with Postfix makes an excellent mail transport, rock-solid (it'll run 'til the hardware fails) and it's free.

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Re: other OSs, I would guess from the context that Win2K is what the OP (or the OPs friend) knows. Using an OS that you don't know for a critical function can only cause trouble. Good point about port 25 though. – 21st Century Moose Feb 13 '10 at 18:07

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