Need some help setting up OpenVPN on Windows 2008 R2

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jetter
OpenVpn Newbie
Posts: 2
Joined: Fri Oct 09, 2009 7:44 pm

Need some help setting up OpenVPN on Windows 2008 R2

Post by jetter » Fri Oct 09, 2009 8:29 pm

My current setup is Windows 2003 Server running OpenVPN 2.1_rc7 and windows XP
for the client on my notebook. Its just a simple personal VPN connection from work to my home network. The only odd thing about it is that I have it set to to use port 443 since it was the only
port not being blocked by the firewall at work. Anyway I have been using this setup
for close to a year and havent had any issues with it.

So now im setting up a new home server using Windows 2008 Server R2 and the latest
OpenVPN client. I have copied over the certificate files from the old server and updated
the path to the correct locations on the new server. OpenVPN installs just fine and I can
start the GUI, click connect and get the green sys tray icon.

the new server is using the same IP address and computer name as the old server (the old
server is turned off). I have a netgear router forwarding port 443 to the vpn server.

Here is the part I cant figure out. If I bring my notebook to a friends house and try
to connect to the new home vpn server, it works flawlessly. If I bring the same notebook
into work and try connecting It fails with a line like this one

failed, will try again in 5 seconds: Connection timed out (WSAETIMEDOUT)

If I turn off the new server and start the old one up I can then connect to it just fine
from work or a friends house. So nothing has changed on the client or the firewall at work\home.
Im using the exact same config files\certs as the old server had. So i dont think the
issue is with that either. the only change I made was pointing them to the new location
of c:\program files (x86) instead of c:\program files, etc. nothing else has been altered on
the config files since copying them from the old server.

Here are some of the things I have tried on the new server so far

Updated to latest NIC drivers.
disabled the public and private firewalls completely
Whitelisted the openvpn.exe file on the disabled firewall (just in case)
created a rule to allow port 443 thru the disabled firewall (just in case)
tried starting openvpn as a service
tried starting openvpn GUI with administrator priveliges
disabled IPv6 on the openvpn adapter
tried updating the client to the latest openvpn client
rebooted many times

If I look at the logs I dont see any errors or connection attempts at all.
Also nothing in the event viewer that would give me any clues.

It sounds like a firewall issue but they have been completely turned off and it still doesnt connect from work

I cant figure out why it works from a friends house but not at work lol

anyone have any ideas?

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ecrist
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Re: Need some help setting up OpenVPN on Windows 2008 R2

Post by ecrist » Mon Oct 12, 2009 11:34 am

could you post your logs either here or to a pastebin and link here? sometimes what doesn't mean anything in the logs to you will clue someone else in to the issue. We would need both client and server logs.
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jetter
OpenVpn Newbie
Posts: 2
Joined: Fri Oct 09, 2009 7:44 pm

Re: Need some help setting up OpenVPN on Windows 2008 R2

Post by jetter » Wed Oct 14, 2009 2:12 pm

Ok I think I got it figured out. in Windows 2008 there is a private, public and a domain
firewall. I had the public\private firewalls turned off but apparently the domain firewall
was stopping the connection. Still not sure why it would work at all at my friends house
with the domain firewall active but at least its working now lol

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ecrist
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Re: Need some help setting up OpenVPN on Windows 2008 R2

Post by ecrist » Wed Oct 14, 2009 6:25 pm

Thanks for letting us know what the problem was. Where did you have to go to view those settings and update them?
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