Running ansible from a windows host

This is partly based on instructions from 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
  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).