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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?

1

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>

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