[shawnz]

You can defeat deep packet inspection by tunneling it over an HTTPS proxy, using the SSH ProxyCommand option and the proxytunnel utility

[varenc]

A corporate IT admin would probably detect this by pulling information directly from the company managed machines. i.e. osquery

https://www.metalliccode.com/detecting-ssh-tunnels

[Jedd]

I worked for an organisation that decided to stop outbound SSH for reasons that weren't adequately well explained, exceptions were painful to get re-applied, so most people just cranked up corkscrew and did precisely this.

Only challenge is that getting corkscrew compiled on Windows is a massive pain.

[n] https://github.com/bryanpkc/corkscrew

[kazinator]

The core API's of Windows are so stable that if someone got it working once on WIndows NT, the executable should work for everyone on Windows 2000, Windows XP, Windows Vista, Windows 7, 8 and 10, ...

[Jedd]

Yup - one of my smarter colleagues had a go at getting it compiled on Windows, and basically gave it up as the library dependencies were such a mess on that platform.

No one seems to have packaged up binaries for it either.

[mycall]

> Win32 (with Cygwin)

Is that good enough support?

[Jedd]

Are you saying that's an environment in which you can compile it?

We tried.

MinGW refers to headers from BSD sockets, which doesn't exist on windows.

[LilBytes]

We had a sys. admin who did exactly this to access his home computer to play World of Tanks. :)

He still works there in a Government Agency riddled with staff who are perfectly adapt at doing enough to stay hired and doing little enough to describe their job as a paid hobby.

[saagarjha]

Trying to defeat measures that your corporate IT department has put up sounds like an excellent way to be terminated.

[yownie]

or just sshuttle

[shawnz]

Sshuttle solves a different problem. It uses SSH as a transport so it could not bypass a firewall that blocks outgoing SSH.