Thanks to Kevin Hilton: How to uninstall/install cygwin under Vista: Uninstall Steps (From previous attempted failed installations) In Administrator shell 1. net stop sshd 2. cygrunsrv -R sshd 3. net user Delete any user listed like sshd or sshd_server. The following syntax is to be used: net user sshd /DELETE 4. rm -R /etc/ssh* 5. mkpasswd -cl > /etc/passwd 6. mkgroup --local > /etc/group In User shell 1. cd ~ 2. rm -R .ssh *********************************************** Installation Steps In Administrator shell 1. ssh-host-config -y 2. net start sshd In User shell 1. ssh-user-config (Answer questions as appropriate to your situation) 2. Test connection: ssh -vvv localhost