Windows & DOS: Issues & Discussions

These are the defaults anyway for those attributes (see man sshd_config)
This sounds strange, as to my knowledge /var on a Unix-like system should either be owned by root or bin.
Also why were you using a relative path when you issued the chown command,
and what directory were you in when you did it?
The $ in your prompt implies to me that you were issuing the chown as a non-root user which without sudo or similar also looks strange to me.
But I guess this all refers to the sshd server running in Cygwin where ownerships and admin rights may differ strangely.
Sorry, I have no Cygwin sshd setup experience to tell if this is all normal.

There actually is no "root" in Cygwin. Since SSHD is run as a service on Local System, everything must be owned by "SYSTEM". I am an Administrator on this machine so everything that root can do on an actual Unix system, I should be able to do in Cygwin.

After a few attempts to yank my hair out I finally got the SSH server working in Cygwin. Basically the key was removing the service from the registry using cygrunsrv –R sshd. Then I just ran ssh-host-config again and made sure the “sshd_server” user is configured correctly and running the service. I guess in Windows 2K3 the it can’t be run as Local System. From there it’s business as usual. I do thank you for all your help. If you happen to come across anyone else having the similar issues setting one up this should help.