knife-windows plugin adds additional functionality to the Chef Knife CLI tool for configuring / interacting with nodes running Microsoft Windows. Bootstrap of nodes via the Windows Remote Management (WinRM) .aspx) or SSH protocols Remote command execution using the WinRM protocol Utilities to configure WinRM SSL endpoints on managed nodes Few Good Helpful Links. Knife Windows git-src-location Awesome Blog Post by Matt Wrock - For More Trouble Shooting Information Installing gems Installing necessary gem for the windows deployments. chef gem install winrm chef gem install knife-windows Setting up Run Enable-PSRemoting (Use a Administrator PowerShell) Open the firewall with: netsh advfirewall firewall add rule name="WinRM-HTTP" dir=in localport=5985 protocol=TCP action=allow [On a Test Machine Disable Firewall till you test chef bootstrap] Run these commands: winrm set winrm/config/client/auth '@{Basic="true"}' winrm set winrm/...