Kitchen-Vagrant has the capability to spin up a windows instatance for testing. To make it make it work you will need the vagrant-winrm to be installted on the workstation. Installing vagrant-winrm ┌─[ahmed][zubair-HP-ProBook][~/work] └─▪ vagrant plugin install vagrant-winrm Once you have have installed you might still get the below error. ┌─[ahmed][zubair-HP-ProBook][~/work] └─▪ kitchen list ------Exception------- Class: Kitchen::UserError Message: WinRM Transport requires the vagrant-winrm Vagrant plugin to properly communicate with this Vagrant VM. Please install this plugin with: `vagrant plugin install vagrant-winrm' and try again. Please see .kitchen/logs/kitchen.log for more details Also try running `kitchen diagnose --all` for configuration Download Windows Box. There is a nice repos which creates windows vagrant box. git clone https: / /github.com/boxcutter /windows.git Here is the output. ┌─[ahmed][zubair-HP-ProBook][~/work] └─▪ git clone https://...