Remote Desktop to a Windows 2008 SBS server via VPN

Posted on 2009-12-18
Last Modified: 2013-11-21
Good afternoon,

I'v got a problem with a windows small business server 2008. the problem is as followed:

I'v got a windows SBS 2008 that acts as a VPN server.
I can make a VPN connection to this server. but i cant connect a remote desktop session to this server trough the VPN connection (This worked fine till 4 days ago)

The odd thing is, when i am in the network itself (So at location at the office) i can remote desktop to server no problem.

Any help on this problem would be much appriciated,


Martijn Boeve
Question by:tinus67
    LVL 12

    Assisted Solution

    DO you have TCP port 1723 open on your router?
    LVL 77

    Assisted Solution

    by:Rob Williams
    Are you connecting from the same site that worked before? If not might the local and remote sites use the same subnet such as both using 192.168.0.x? They must be different.

    Also why not use Remote Web Workplace built in to SBS. It is more secure, and doesn't require using the VPN?

    Author Comment

    The port 1723 is checked and open, but that wasnt the problem really as a VPN connection can be made without problems.

    Also the subnets for the local and remote sites are different, so probely no problem there either. the configuration as it stands now worked 4 days ago. anyway the remote web workspace is being used as wel by the users in the company that works no problem on all the pc's and the other servers but the Main server can't be accessed by remote desktop over the VPN connection. i am part of the company that manages this network, and we use VPN and remote desktop to access the servers. so therefore i would like to try and fix this problem.

    Thanks for the fast reply's
    LVL 77

    Assisted Solution

    by:Rob Williams
    With SBS the VPN should be configured using the wizard on the network / connectivity page of the SBS management console. I would re-run the "fix my network", on the same page wizard (which works miracles) and if that doesn't work try re-running the SBS VPN wizard.

    Often the problem is the Windows firewall is enabled, has an exception for the VPN, but is not configured to allow your remote subnet. Perhaps someone tweaking or an update has made changes to this or a similar feature. The wizards should automatically check/fix this.

    Accepted Solution

    havent been able to fix this issue yet. for now i opend a port to connect to this server directly.

    Thanks for the responces.

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