> Can anyone recommend another solution to have encrypted, secure file
> sharing between Windows machines and UNIX (specifically OpenBSD)?

I've been looking into this problem recently myself and you might be
able to use my information.

There is a port of openssh for windows. It's a console util that works
just like it's *nix cousin, and it can handle tunneling. Example:

ssh -L 137:files.domain.com:137
ssh -L 138:files.domain.com:138
ssh -L 139:files.domain.com:139

The Windows port of openssh can be found here:
http://www.networksimplicity.com/openssh/

As for older OSs that have to have UDP to do things like browsing,
etc., there's a way to handle that as well. Netcat will happily pipe
UDP packets into a TCP stream:

#client side
ssh -L 9137:files.domain.com:9137
ssh -L 9138:files.domain.com:9138
ssh -L 9139:files.domain.com:9139

nc -l -u -p 137 | nc localhost 9137
nc -l -u -p 138 | nc localhost 9138
nc -l -u -p 139 | nc localhost 9139

#server side
nc -l -p 9137 | nc localhost -u 137
nc -l -p 9138 | nc localhost -u 138
nc -l -p 9139 | nc localhost -u 139

I'm not sure if you'll need to install the Cygwin bash port in order
for Windows to handle the piping properly, or if the Windows port of
Netcat will handle that for you. By the way, Netcat for Windows is
here: http://www.atstake.com/research/tools/.

I haven't tested this, but I believe the theory behind this is sound.

Hope this helps!

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