This is partly based on instructions from https://servercheck.in/blog/running-ansible-within-windows but uses a virtual environment and no checking out from Github / manually installing packages.

1. Install Cygwin. Include following packages:
   • python
   • openssl / openssl-devel
   • python-crypto
   • python-openssl
   • openssh
2. Install & configure pip, virtualenv & virtualenvwrapper as per http://atbrox.com/2009/09/21/how-to-get-pipvirtualenvfabric-working-on-cygwin/
3. Create a virtual environment for ansible with mkvirtualenv --system-site-packages ansi
4. Install ansible inside your virtual environment with pip install ansible pyyaml jinja2

That’s it (remember to set ssh_args = -o ControlMaster=no  in ansible.cfg as cygwin doesn’t support it).