I work for a small company where we have a windows 2000 server domain(not 2003). For a little history, we’ve had a couple of different IT consultant companies taking care of our network over the last couple of years. When we had our original IT company, who setup the server and domain, everything with VPN and Remote Desktop were working fine. I mention this since each of these consultants have used different remote administration software to work on our servers(some of which have been un-installed), which could be contributing to our problem. We also do not have a full-time onsite IT person, though I have a strong understanding of domain admin, so I get the day to day little fixer problems. So here is the problem:
Server 2000 – This is our VPN server, File server, IIS server, and Exchange server (I know that’s a lot, don’t get me started). It obviously has both a live IP address for VPN and IIS as well as another adapter with a Private IP address for it’s file server duties.
Remote Desktop ‘targets’ – Multiple desktop machines running Windows XP, all of which are part of the domain. These machines are inside the firewall, and are served out private ip addresses from our DC. We have tried to connect to these computers via IP address and Computer Name, from outside of the domain without success.
Now, again, previously, our VPN, Firewall, etc. were all configured correctly and we were able to remote into these private IP machines from outside of the domain by turning on the VPN connection. Now the only way we can remote into these machines is to Remote into our server, then in that remote session, create a remote session to the private machines. We were really not able to pinpoint what happened that caused this to suddenly stop working for the machines with private IP addresses. The Windows 2000 server that has a live IP is accessible via Remote desktop sessions, but none of the private IP machines.
Any ideas of what may have happened here? Could it be that when some of the old remote administration programs left behind files/registry entries that are causing issues with address resolution?
We want to get back to the point where we can remote into our desktop machines from offsite without having to go through multiple Remote Desktop sessions. Any help pointing me in the right direction for research or a solution would be very helpful.