You can either alter the parameters of your currently installed server to enable debugging or install another that has the debug parameters. I prefer the latter since that doesn't overwrite the normal sshd service. If you check out '/usr/bin/ssh-host-config', there's a line in there with 'cygrunsrv -I' that you'll want to replicate and modify for your needs if you want to set up a new service. Something like this should work though, assuming you've already run '/usr/bin/ssh-host-config' before to set up the normal sshd service. /usr/bin/cygrunsrv -I sshd -d "CYGWIN sshd_debug" -p /usr/sbin/sshd -a "-D -d -d -d" -y tcpip The service starts automatically. You'll have to manage which one (the normal or the debug) that you want started automatically, depending on you need. You don't want both the debug and normal sshd services to be running at the same time. Keep in mind that the debug service terminates after the first connection ends.