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Please excuse my inexperience. I managed to setup a vpn connection between a single client and server. Currently I am testing this in VM's which are running Server 2008 R2 (temporary since I have install disks handy). Each VM is in a remote location with its own IP address. (I am remoting in).

What is happening is that I am able to ping the VPN Server from the client with no problem. once I attempt to ping another device on the network (say server is 192.168.1.2 and other device is 192.168.1.3) i am getting request timed out. The tracert has the packet being routed through the VPN to the Virtual Gateway of 10.8.0.1. Also I am not able to ping from the server to the client. ie ping 192.168.2.3

Below is a simple topology.

[Network 1] Hosts server on 192.168.1.2 192.168.1.0 | 255.255.255.0

[Network 2] client on 192.168.2.3 192.168.2.0 | 255.255.255.0

[VPN Server] 10.8.0.1 10.8.0.0 | 255.255.255.0

So essentially from running tracert on client side I am getting...

1 30ms 40ms 20ms HOME [10.8.0.1]

2 * * * Request timed out.

etc...

Meaning the packet is reaching the server but not being routed from server to machine on same network.

I realize there could be several problems so even a direction would be greatly appreciated. The openvpn logs are just showing ipv6 routing warnings but I am not using ipv6 so i am assuming this can be ignored.

I used this tutorial to setup the server and client http://www.smallnetbuilder.com/security/security-howto/30353-how-to-set-up-a-site-to-site-vpn-with-openvpn?showall=&start=1

Maurycy_was_userxxxxxx
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  • Is packet forwarding turned on? I'm not sure how one would do this in Windows. – cjc Sep 12 '11 at 19:28
  • Its likely i didn't setup my routs correctly i guess that's how packet forwarding is handled. I'm going to double check right now – Maurycy_was_userxxxxxx Sep 12 '11 at 19:36
  • I double checked my routes and I am still not certain where the problem lies. any ideas? – Maurycy_was_userxxxxxx Sep 12 '11 at 20:38
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    Did you enable Forwarding? http://blogs.technet.com/b/networking/archive/2008/11/20/balancing-act-dual-nic-configuration-with-windows-server-2008-nlb-clusters.aspx basically the registry change for IpEnableRouter. – cjc Sep 12 '11 at 21:07
  • It Finally works! Thank you CJC, I did do that earlier and it still did not work. What I did was essentially removed all old config files and redid my setup following this tutorial which is centered around windows vs linux... http://www.runpcrun.com/howtoopenvpn . I had to delete my previously set routes ( i just ran route -f which deletes all routes [don't do this on a production server] and then openvpn setup the routes for me which I specified in the .ovpn file. ). After making sure my router is pointing all the packets for the tunnel to the openVPN server I was able to ping my clients. – Maurycy_was_userxxxxxx Sep 13 '11 at 18:33

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