If I run an SSH server on my Windows 2008 server box on the default port 22 I always get Operation Timed Out on the client. If I run it on another port (say 2222) it works fine. I've opened up the firewall. Netstat shows that the server is listening on the correct port. I have used two different Windows SSH servers (freeSSHd and WinSSHD) and they both have the same result. What else could be causing the difference between running the SSH server on port 22 versus port 2222?