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I have an OpenVPN instance set on a VPS. I'm connecting to it through my university's firewall. They've blocked everything (including ssh!). So, I have setup my OpenVPN and everything works fine when I connect through my home connection. When I try to connect through my university, I get this: 

Tue Mar 15 09:57:40 2011 us=482000 TCP connection established with 78.138.13.91:80
Tue Mar 15 09:57:40 2011 us=482000 TCPv4_CLIENT link local: [undef]
Tue Mar 15 09:57:40 2011 us=482000 TCPv4_CLIENT link remote: 78.138.13.91:80
Tue Mar 15 09:57:40 2011 us=482000 TCPv4_CLIENT WRITE [14] to 78.138.13.91:80: P_CONTROL_HARD_RESET_CLIENT_V2 kid=0 [ ] pid=0 DATA len=0
Tue Mar 15 09:57:40 2011 us=872000 TCPv4_CLIENT READ [26] from 78.138.13.91:80: P_CONTROL_HARD_RESET_SERVER_V2 kid=0 [ 0 ] pid=0 DATA len=0
Tue Mar 15 09:57:40 2011 us=872000 TLS: Initial packet from 78.138.13.91:80, sid=5cb8cc85 0057a337
Tue Mar 15 09:57:40 2011 us=872000 TCPv4_CLIENT WRITE [22] to 78.138.13.91:80: P_ACK_V1 kid=0 [ 0 ]
Tue Mar 15 09:57:40 2011 us=872000 TCPv4_CLIENT WRITE [108] to 78.138.13.91:80: P_CONTROL_V1 kid=0 [ ] pid=1 DATA len=94
Tue Mar 15 09:57:42 2011 us=42000 TCPv4_CLIENT WRITE [108] to 78.138.13.91:80: P_CONTROL_V1 kid=0 [ ] pid=1 DATA len=94
Tue Mar 15 09:57:46 2011 us=722000 TCPv4_CLIENT WRITE [108] to 78.138.13.91:80: P_CONTROL_V1 kid=0 [ ] pid=1 DATA len=94
Tue Mar 15 09:57:55 2011 us=146000 TCPv4_CLIENT WRITE [108] to 78.138.13.91:80: P_CONTROL_V1 kid=0 [ ] pid=1 DATA len=94
Tue Mar 15 09:58:11 2011 us=214000 TCPv4_CLIENT WRITE [108] to 78.138.13.91:80: P_CONTROL_V1 kid=0 [ ] pid=1 DATA len=94
Tue Mar 15 09:58:40 2011 us=589000 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
Tue Mar 15 09:58:40 2011 us=589000 TLS Error: TLS handshake failed
Tue Mar 15 09:58:40 2011 us=589000 Fatal TLS error (check_tls_errors_co), restarting
Tue Mar 15 09:58:40 2011 us=589000 TCP/UDP: Closing socket
Tue Mar 15 09:58:40 2011 us=589000 SIGUSR1[soft,tls-error] received, process restarting
Tue Mar 15 09:58:40 2011 us=589000 Restart pause, 5 second(s)

Any ideas on how to proceed with debugging this issue? I can see that port 80 is working since I get the first packet but why does it stop after that?

(Another hint, skype shows the green 'connected' icon in the system tray but it isn't really connected. I think the issue is pretty much the same with both.)

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Try setting your server to listen on udp/53. DNS is commonly overlooked. Or your university may have a transparent proxy. Figure out what is and then try to configure openvpn to use the proxy. – Zoredache Mar 15 '11 at 2:15
As a member of this forum once said to me rare will be person wishing to help you breaking rules put in place by your university, but I personally find those rules stupid for the most. – Gopoi Mar 15 '11 at 3:52
I know it's not good but come on! I'm just trying to ssh. How am I supposed to get anything done when they're blocking ssh and allowing facebook! – recluze Mar 16 '11 at 7:08
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Probably because they proxy HTTP traffic (that is, pull it apart, realise it's not website traffic and throw it away). You might have more luck with HTTPS as long as they don't do man-in-the-middle proxying.

By "more luck" I do mean "check the terms of use of your connection, you might face disciplinary action for even trying to circumvent them".

{ I also didn't mention http://www.cs.uit.no/~daniels/PingTunnel/ }

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There's also iodine – ptman Mar 15 '11 at 8:16
That's a good idea. I will not try that out ;) – recluze Mar 16 '11 at 7:08
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