Maybe I am the only one, but WinRM is just not cutting it for me anymore.
Some of the problems included poor support for Ruby/Vagrant, the requirement to use a Windows client unless you want to loosen up security, and no cert-based authentication.
I really wanted a single method to communicate with my servers, a single certificate, and be able to use Windows or Linux clients.
I finally gave up and created an open source cookbook that installs and configures OpenSSH on Windows.
It has it's quirks, but overall is working great. I can scp files to the windows box, execute chef-client, and do a msdeploy all from scp/ssh commands on a Linux, Mac, or Windows client..