I have a server at a remote site, the sites are connected to each other a site-to-site VPN connection using Cisco ASA 5510 firewalls. One end is managed by me, the other managed by the remote location's IT, between the 2 of us is another party who manage and route the connections.

Remote desktop has been working fine with no problems then recently I noticed it was working for ONE server over the VPN which it previously had done. All the routes seem fine and I can still ping the remote server and even download files from an FTP site on the remote server.... so the VPN seems fine.

Remote Desktop works fine to the remote server within the remote location but not over the VPN. I don't understand why it's stopped working, I originally thought it was a rule in place by the other party but they stress it's not them.

The only thing that has changed on the server initiating the RDP connection is that it now runs file services sharing a folder. The source server (remote location) may or may not have had updates applied.

Any idea's?

  • More details. OS on both ends... and what is the error message? – TomTom Mar 9 '10 at 14:55
  • OS on the initiating server is Server 2008 R2, the remote location server is Server 2003 32bit. Error message is the remote desktop connection couldn't connect. I can ping the server also. I'm thinking it may have something to do with file services...perhaps! – stead1984 Mar 9 '10 at 14:58
  • UPDATE- I did the classic turn it off and on! I'm thinking it may have something to do with the initiating servers RDP listening port not closing correctly? Any thoughts! – stead1984 Mar 11 '10 at 8:59

So the initiating server was able to connect at one point and now all of the sudden it cannot? And the only thing you know that has changed is the initiating server has file services installed?

Could perhaps a default setting been changed? I know that on server 2008 systems there is some setting to allow remote desktop connections for older remote desktop connection applications from older systems. Is there a setting to allow you to remote connect to older remote desktop connection systems?

Has anything changed on the 2003 system? Can you verify it can accept connections? Try to initiate the connection from another host. For instance do you have an XP client or another server 2003 system you could attempt to initiate the connection from? If that works then the issue would likely exists on the server 2008 system. If not, then it is either an issue with the server 2003 system on the other side of the tunnel or a network issue.

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Try connecting (or having the other guy(s) connect) with a client on the other side.

There should be no problem connecting to a lower version, regardless of remote settings, as long as it is still turned on and allowing the user you are connecting with.

Disable firewalls on receiving server for a brief moment, try it then. No real danger if this is a closed off network, which your VPN suggests it is.

What does event viewer say happens on the receiving server?

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  • It doesn't say anything at all about a failed connection on the receiving server, the traffic is going over the VPN connection but going by the event viewer it's not getting to the server. – stead1984 Mar 9 '10 at 18:08

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