I always forget these simple steps..and ALWAYS end up googling for it..
here goes:
1. On installing Cygwin, make sure to choose “Install for Everyone”, then, after choosing a mirror, go to the NET group and find OpenSSL and OpenSSH, tick once to install.
2. Copy Paste all of the below:
chmod +r /etc/passwd
chmod +r /etc/group
chmod 755 /var
ssh-host-config –y
above has a –y at the end, this means it will default to answering everything with a “yes”.
from my experience, you can do this only when you are sure your environment makes sense, its usually better to say “yes” manually and follow every step carefully.
export CYGWIN=ntsec tty
cygrunsrv --start sshd
Now.. on some machines, like some company based ones, you may have a default home profile which doesn’t go well with CygWin, in that case, you may change the passwd file under /etc/passwd to provide a more helpful location.
Another point to take into account, when using this in conjunction with Git for instance, is that Git should be installed with the safest option, where it doesn’t interfere with the Windows PATH or anything like that.
This makes sure CygWin will listen to Git’s requests when pulling and pushing.
Even when taking all of that into account, this may not work too well in Windows 2003 
This alone validates my previous managers’ comments on why they dont want to have sshd..its sad.. and I wish the cygwin folks would make it more click friendly..
Anyway, it works for me and I love it!
Good job!
