troubleshooting Question

**URGENT** IIS HTTP 500 Internal Server Error

Avatar of simonprr
simonprr asked on
Windows 2000
15 Comments1 Solution1087 ViewsLast Modified:

This question is very urgent as I have a problem with a website that my company hosts (or needs to host!). The setup is a bit complicated to explain, so I'll try my best.

The setup:

Windows 2000 Server SP3 (Can't go to SP4 yet - not the standard. But if there is a fix in there which fixes this I may have a case to do it)
IIS 5.0
.NET Framework 1.1
This server is in a DMZ (firewall either side of it - 1 between my companies network and 1 between the internet and it)
The internet firewall also using NAT, so it's something like this (for example):

Internet ( -> Server IIS Website (

This server has multiple websites setup on it, each with a different IP, the default not running and 3 others. 2 of them work fine. The 3rd doesn't just always gives me a HTTP 500 Internal Server Error. Turning on show friendly error messages just gives me "Internal Server Error". Bear in mind that this server also has IPs and Then each of these IPs are NATed to internet IPs which have hostnames on the internet (for the different websites). These hostnames are in the host header fields of each in IIS too.

All I am trying to get to work (firstly) is the showing of a simple HTML page, but it won't even show that! It works when I create a virtual directory to this website that doesn't work, from a website which does, but not as the actual website.

So any ideas? I have seriously tried everything... anonymous access is enabled, NTFS rights are everyone, most settings are default, running on port 80.... Could the fact that we have 3 websites running on the same box make a difference? I've been through MSKB article regarding this error, but none of the "fixes" fix it. I guess it could be some werid routing error... but what I have no idea. I really just have no ideas left!

Please help.
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