Just want to thank the experts in advance:

I have 2 web servers running Windows Server 2003 Web Edition that are load balanced. They are on a DMZ along with another server, connected to a Cisco PIX firewall. On the web servers, I have the other server as the SMTP Smart host, so when my ASP pages send an email, the SMTP server is routed to the Smart host, which then routes the message to an Exchange Server on an internal subnet. One of the web servers works fine. It’s just the one that I recently installed Windows Updates. Ever since then every time I send an email, it gets stuck in the mailroot\Queue folder.

I was getting this System event log error: Message delivery to the remote domain 'stroman.com' failed for the following reason: The connection was dropped by the remote host.

This is my troubleshooting so far, but still no luck:
1. Restarted IIS
2. Uninstalled SMTP Windows Update (KB885881)
3. Reinstalled IIS
4. Uninstalled Lan Gaurd Network Security scanner (After I did this I no longer got the System event error mentioned above)
5. Followed this http://www.experts-exchange.com/Web/..._20794824.html article and performed the troubleshooting defined in there. This guy is having the same problem almost exactly. However, his case was basically unresolved. I used telnet to send an email message, which the SMTP server didn't relay to the smart host. I also enabled SMTP logging, if anyone knows how to read it.

Any help or ideas would be greatly, greatly appreciated. Thanks again.

Bryan Moore
Webmaster