I'm currently playing with Windows Server 2008 Core and I'm really at a loss trying to figure out why Microsoft seems to go out of its way not to adopt SSH. SSH seems like such an easy and straightforward answer to remote administration. Unix administrators have long used SSH but Windows administrators are given WinRS, a command line tool that requires that you run it each time you need to execute a command on a remote system. So instead of arriving at a remote prompt as you would with SSH and simply typing "ipconfig", you must type "winrs -r:myserver ipconfig"
winrs -r:myserver every time!
I'm hoping things have changed in Windows 2008, but so far, I can't find any way for WinRS to be interactive. A blog post on TechNet back in 2006 suggests that interactivity is going to be a feature at some point:
Currently any commands you execute can't be interactive or prompt for input. WinRS just executes what you specify and returns the results.
Unfortunately, it's nearly a year and a half later and no progress seems obvious. I hope I'm wrong and someone can show me the light or, even better, perhaps we'll see PowerShell+SSH hit the final version of Windows 2008. Many admins already have an SSH client as part of their toolkit and sure, WinRS runs over HTTP(S) and opening just one port is nice but the same goes for SSH. Port 22 or 80, I don't really care. WinRS seems to have its value, but not as a replacement for SSH. Give me SSH or give me both.