I have 3 Windows 2003 servers in a domain. Server 1 is running the AD and VPN roles. Server 2 is running Exchange 2003. Server 3 is running some third party network apps and was supposed to be running the VPN role. They are all in the same subnet 192.168.1.0/24.
Recently I was running Windows updates on all of them and realized that Server 1 and Server 3 get stuck at "Waiting for response..." in my IE window where the windows updates are running. So after about 5 minutes of waiting windows update gives up and just shows a website not found error. Server 2 meanwhile has no problems downloading updates. The other odd (possibly related) thing is that both Server 1 and Server 3 are unable to access our phone system's web interface which is on a server at IP 192.168.2.50 (note the different subnet). While Server 2 can access the web interface at 192.168.2.50. The reason I think its related is because a few months ago I was trying to setup automatic backup over FTP from the phone system (192.168.2.50) to the Server 3, and the FTP connection would mysteriously keep failing. I could never figure out. But once the Windows Update issue happened, I tried setting up the FTP transfer from the phone system to Server 2, and it worked flawlessly. The only difference right now between Server 2 and Server 1/3 is that Server 1/3 have the VPN/RAS role (see number 9 below).
A few things I've tried
- Restart both Server 1 and 3.
- Disable Windows Firewall.
- Disable the Anti Virus program (I'm using Trend Micro).
- Check the routing tables on all servers for any conflicts/inconsistencies (using route print/route add/route delete). Again just precautionary, don't think this is the issue because ping (ICMP) and nslookup (DNS) all work fine.
- Run a ping test which works fine. Now I can ping from Server 1 and 3 to the phone system (192.168.2.50) and microsoft websites. But HTTP still fails. I even tried a raw HTTP test using telnet (and GET request).
- Add the microsoft domain and related windows update domains to the list of trusted sites in Internet Options.
- Run netdiag on Server 1 and 3. No issues. DNS and DHCP are fine.
- Run DNS lookup tests. They are successful.
- Remove the VPN/RAS role from both servers 1/3 and attempt windows updates.
- Check my router for any specific deny rules.
Any ideas? I was going to run a Wireshark scan, but I really do'nt know what to look for.
Remember I can still surf the web like www.google.com etc from Server 1/3.