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Installing Ansible in Cygwin on Windows 7

This document describes installing and running Ansible in Cygwin on Windows 7.

Step 1: Download cygwin

Download the standard cygwin setup.exe and run it.

Step 2: Select cygwin packages

Select to install the following packages.

  • python2-setuptools

  • python

  • python-devel

  • python-crypto

  • gmp

  • libgmp-devel

  • libffi-devel

  • openssl

  • openssl-devel

  • git

  • openssh

  • gcc-core

  • gcc-g++

  • make

And any other packages you might need personally.

Step 3: Create virtualenv

If file names differ try tabbing to auto-complete them in your cygwin.

$ easy_install-2.7 pip
$ pip install virtualenv
$ mkdir -p .venv/ansible2
$ virtualenv .venv/ansible2
$ source .venv/ansible2/bin/activate

Ensure you activate the virtualenv for the next step so you don't install Ansible globally.

Step 4: Install Ansible

As of writing this, 2017-02-24, pycrypto suffers a bug on cygwin that prevents it from compiling. 

$ CFLAGS="-g -O2 -D_BSD_SOURCE" pip install -U pycrypto
$ pip install ansible

Step 5: Disable ControlMaster

Ansible in Cygwin does not work with ControlMaster so you must disable it in ansible.cfg.

[ssh_connection]
ssh_args = -o ControlMaster=no
Last update: September 19, 2021