Windows OpenSSH - oclhc+ interactivity

[epixoip]

Probably just some weirdness going on with your SSH setup on Windows, its terminal emulation, etc. Solution is likely just to not do it that way. If you're comfortable with Cygwin and doing things over SSH, it would probably be best to run Linux on your cracking rig. If Linux is not an option, the next best way would be to use a native Windows solution like RDP.