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Running OpenVPN with Windows 2000

Posted on 2007-04-01
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I recently have been testing OpenVPN on Windows machines.  I am able to configure networks between Windows XP machines without a problem.  However if I try and setup a Windows 2000 Server as a VPN server or client, the connection never works.  Basically the machines seem to connect but after the client receives its IP address, it ping fails to work from the client to server and vice versa.  There are no firewall issues and I am running OpenVPN 2.0.9.

Testing Environment:
I have a XP and 2000 box at the office and at home I also have an XP and 2000 box.  Connecting both XP computers is no problem, however if the 2000 box fails as a client and server.

The documentation says that OpenVPN is compatible with Windows 2000 so maybe someone can help me sort this out.  It is also possible that setting up an Ethernet bridge could be an alternate option but I have yet to figure out how to configure that feature.
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Question by:lex917
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kadadi_v earned 2000 total points
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by:edwarneke
ID: 18846306
Although I cannot comment on your particular setup, we have an OpenVPN 2.0.7 server running on CentOS4 and multiple win2k clients(both 2.0.7 and 2.0.9) connecting to it with no issue. We use certificate based authentication and the IP range handed out is 10.x.x.x and our local network(network being vpned into) is 192.168.x.x.
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