Openvpn – Setting HTTP proxy in OpenVPN client

httpopenvpnPROXY

I'm having trouble configuring my OpenVPN client to use an HTTP proxy.

If I don't enter any proxy information in the client.ovpn file I get the following output:

Mon Jun 29 14:30:07 2015 OpenVPN 2.3.7 i686-w64-mingw32 [SSL (OpenSSL)] [LZO] [PKCS11] [IPv6] built on Jun  8 2015
Mon Jun 29 14:30:07 2015 library versions: OpenSSL 1.0.1m 19 Mar 2015, LZO 2.08
Mon Jun 29 14:30:07 2015 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:25340
Mon Jun 29 14:30:07 2015 Need hold release from management interface, waiting...
Mon Jun 29 14:30:08 2015 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:25340
Mon Jun 29 14:30:08 2015 MANAGEMENT: CMD 'state on'
Mon Jun 29 14:30:08 2015 MANAGEMENT: CMD 'log all on'
Mon Jun 29 14:30:08 2015 MANAGEMENT: CMD 'hold off'
Mon Jun 29 14:30:08 2015 MANAGEMENT: CMD 'hold release'
Mon Jun 29 14:30:08 2015 Socket Buffers: R=[8192->8192] S=[8192->8192]
Mon Jun 29 14:30:08 2015 UDPv4 link local: [undef]
Mon Jun 29 14:30:08 2015 UDPv4 link remote: [AF_INET]x.x.x.x:x
Mon Jun 29 14:30:08 2015 MANAGEMENT: >STATE:1435581008,WAIT,,,
Mon Jun 29 14:31:08 2015 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
Mon Jun 29 14:31:08 2015 TLS Error: TLS handshake failed
Mon Jun 29 14:31:08 2015 SIGUSR1[soft,tls-error] received, process restarting
Mon Jun 29 14:31:08 2015 MANAGEMENT: >STATE:1435581068,RECONNECTING,tls-error,,
Mon Jun 29 14:31:08 2015 Restart pause, 2 second(s)

Please note I replaced my actual VPN IP with x.x.x.x:x

This doesn't work because I'm behind a proxy.

When I edit the client.ovpn file accordingly (or atleast I thought) like this:

# If you are connecting through an
# HTTP proxy to reach the actual OpenVPN
# server, put the proxy server/IP and
# port number here.  See the man page
# if your proxy server requires
# authentication.
http-proxy-retry 1
http-proxy y.y.y.y 8080 (replaced actual IP here)

the VPN client does even less than before.
The log-output stays blank and it displays a messagebox saying: "Connecting to client has failed."

Afaik, the proxy IP is correct. I can telnet to it on the 8080 port.

Any idea what the problem might be?

Best Answer

try editing your .ovpn file like this. put your tcp connection line under connection tag and define all needy_proxy here.

<connection> remote vpn_ip_here vpn_port tcp http-proxy y.y.y.y 8080 (replaced actual IP here) http-proxy-retry </connection>