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Even better trick is SSH can actually tunnel level 3 data! Via TUN/TAP interfaces (this is effectively how some VPN implementations do it).

See "-w" option

Here are a few guides. This is more involved than just adding the -D option and setting a "proxy" field in some applications but this is more general as well:

http://sleepyhead.de/howto/?href=vpn

https://wiki.archlinux.org/index.php/VPN_over_SSH

https://help.ubuntu.com/community/SSH_VPN

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Yes, except for the TCP-over-TCP issue.

Great point, Colin. That probably explains why it is not more popular (or it is rather a new-ish feature...).

I was just surprised it was there.

SSH does it's own flow control, and with HPN-SSH it is much better.

Also, if your connection to the VPN host is quite good, then the TCP-over-TCP issue does not apply as much. The bad cases happen when that connection has packet loss.

All connections have packet loss.

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