OpenVPN Client on Windows Server 2008 R2

dbendlin

Hello Guys,

I've recently setup an openvpn client on a windows server 2008 R2 (openvpn-install-2.3.10-I601-x86_64), the openvpn server runs on a remote location on a debian server (OpenVPN 2.1.3 i486-pc-linux-gnu). Yes, server version is older than client version.

Here's my client config file:

remote w1.x1.y1.z1 1194
remote w2.x2.y2.z2 1194
float
dev tun
proto tcp
tun-mtu 1500
client
ca "C:\\apps\\OpenVPN\\config\\ca.crt"
cert "C:\\apps\\OpenVPN\\config\\vms-client.crt"
key "C:\\apps\\OpenVPN\\config\\vms-client.key"
ns-cert-type server
comp-lzo
verb 3

If I start the vpn using windows explorer context menu (right clic over ovpn config file), a windows terminal will open and client connects to the server, establishes the connection and I can traffic over the tunnel. (No log file is produced to the OpenVPN\log directory since its directed to the windows terminal)

If I open windows services manager, and start the OpenVPN Service, the process runs, this time a log file is writen to OpenVPN\log directory but the client wouldn't connect, this is what I get on that log file:

Wed Jan 27 22:54:14 2016 OpenVPN 2.3.10 x86_64-w64-mingw32 [SSL (OpenSSL)] [LZO] [PKCS11] [IPv6] built on Jan  4 2016
Wed Jan 27 22:54:14 2016 Windows version 6.1 (Windows 7)
Wed Jan 27 22:54:14 2016 library versions: OpenSSL 1.0.1q 3 Dec 2015, LZO 2.09
Wed Jan 27 22:54:14 2016 Socket Buffers: R=[8192->8192] S=[8192->8192]
Wed Jan 27 22:54:14 2016 Attempting to establish TCP connection with [AF_INET]w1.x1.y1.z1:1194 [nonblock]
Wed Jan 27 22:54:24 2016 TCP: connect to [AF_INET]w1.x1.y1.z1:1194 failed, will try again in 5 seconds: The system tried to join a drive to a directory on a joined drive.  
Wed Jan 27 22:54:24 2016 SIGUSR1[soft,init_instance] received, process restarting
Wed Jan 27 22:54:24 2016 Restart pause, 5 second(s)
Wed Jan 27 22:54:29 2016 Socket Buffers: R=[8192->8192] S=[8192->8192]
Wed Jan 27 22:54:29 2016 Attempting to establish TCP connection with [AF_INET]w2.x2.y2.z2:1194 [nonblock]
Wed Jan 27 22:54:39 2016 TCP: connect to [AF_INET]w2.x2.y2.z2:1194 failed, will try again in 5 seconds: The system tried to join a drive to a directory on a joined drive.  
Wed Jan 27 22:54:39 2016 SIGUSR1[soft,init_instance] received, process restarting
Wed Jan 27 22:54:39 2016 Restart pause, 5 second(s)

I allready market the exe files, openvpn.exe and openvpnserv.exe to run with administrator priviledges.

Any help will be greatly appreciated =)

Traffic

What happens if you use openvpn-gui.exe ?

dbendlin

Traffic wroteWhat happens if you use openvpn-gui.exe ?

Thanks for your reply, when I tried to start openvpn-gui it yield an error, it was trying to open c:\Program Files\OpenVPN\bin\openvpn.exe.

I have a convention of using C.\apps instead, so I open regedit and went to Local_Machine > Software > OpenVPN GUI and fixed the entries pointed to c:\program files to c:\apps, after that I was able to use OpenVPN GUI, it worked just fine, and tunnel could be established.

Running as a service still doesn't work =(

What I'm looking forward to do is been able to start openvpn on this windows box automatically and unattended. From what I've seen this seems to be some kind of issue related to openvpn starting as a service, not openvpn itself, is this the right place to ask for help?

Traffic

dbendlin wroteI have a convention of using C.\apps instead, so I open regedit and went to Local_Machine > Software > OpenVPN GUI and fixed the entries pointed to c:\program files to c:\apps, after that I was able to use OpenVPN GUI

It sounds like you moved openvpn .. try uninstall/reinstall to you chosen directory ..

dbendlin

I allready did, same results, I'll be looking for openvpnserv related windows registry entries to check if maybe something needs to be adjusted.

I'll write back to you, thank you.