git push/pull times out

I had exactly the same problem and adding a route for github solved my issues as well.

The command for windows (or cygwin in my case) would be: route add <ip> <gateway>. So what solved it for me was simply: route add 207.97.227.239 192.168.0.1.

Please note the different IP for github.com I used in comparison with the one araqnid had, two years ago. :)

If you are not sure whether your added route still works after some time, just type (on windows or cygwin) tracert github.com to see where the packets get routed. If the first hit seems to be located within your company, the route you added is not valid anymore and you would need to add a new route.

Not sure which type of VPN you're using, but this sort of effect is usually due to the VPN setup routing all your traffic over the VPN. You can work around that by updating your routing tables to route traffic to github back over your Ethernet (I assume) interface rather than over the VPN.

For example route add 65.74.177.129 eth0 will route traffic to github over eth0. This is the Linux syntax; Windows has a "route" command as well that is broadly similar.

(This isn't really a git-specific problem, and in fact you should be able to demonstrate the problem by trying to connect to github.com port 22 with any client such as telnet, nc or PuTTY: sshd will usually print a banner with its version number as soon as you connect)