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Executable wrapper to wrap ansible commands on windows using cygwin and cygwin-python
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Ansible Wrapper for Windows

This is a simple executable wrapper to allow Vagrant to run ansible commands on windows through to a configured cygwin environment. There are a few threads out there that document the use of batch files to bootstrap ansible but I found the windows command shell does not actually work properly when using --extra-vars for instance.

We assume you have installed a working cygwin shell on your workstation.

Wrapper Configuration

The wrapper must be able to find the installed cygwin environment. By default it assumes the cygwin home is c:\cygwin. If your cygwin is installed in a different location there are 2 options available to tell the wrapper where to find the cygwin environment.

  1. Using the CYGWIN_HOME Environment Variable
export CYGWIN_HOME=c:\\cygwin64
  1. Using the cygwin.ini File

The wrapper will look into the directory of the wrapper executable for a cygwin.ini file that contains the below ini information.


Installing Ansible on Cygwin

This section describes the installation steps required to install Cygwin and Ansible on Windows.

Install Cygwin

Use the cygwin package installer from and install the following packages:

setup-x86_64.exe -q -P binutils,^

or using apt-cyg

$ apt-cyg install binutils \
          gcc-core \
          make \
          python \
          python-setuptools \
          python-devel \
          libtool \
          libuuid-devel \
          libffi-devel \
          python-cffi \
          libcrypt-devel \
          python-crypto \
          openssl \
          openssl-devel \
          python-openssl \
          openssh \
          gmp \
          libgmp-devel \
          curl \
          wget \

Now you should have a basic cygwin python environment that can be used to install ansible in.

Configure Python Environment

First lets open up a cygwin terminal and install pip

$ easy_install-2.7 pip

Thereafter we will update pip, setuptools and also install wheel and virtualenv.

$ pip install -U pip setuptools wheel virtualenv

Install Ansible

Before installing Ansible, you will need to install its dependency PyNaCL with additional compiler flags.

ARCHFLAGS="-arch x86_64" \
LDFLAGS="-L/usr/lib" \
CFLAGS="-I/usr/include/openssl -g -O2 -D_BSD_SOURCE" pip install -v -v -v -U pynacl

Now lets install ansible and its dependencies.

$ pip install -U ansible

Quick test to ensure it works.

$ ansible --version
  ansible python module location = /usr/lib/python2.7/site-packages/ansible
  executable location = /usr/bin/ansible
  python version = 2.7.14 (default, Oct 31 2017, 21:12:13) [GCC 6.4.0]

Configure Vagrant Environment to work with Ansible

To bridge Vagrant on windows to Ansible on Cygwin we can now use the Ansible Wrapper for Windows binary. The Vagrant Ansible provisionser will use the Vagrant windows environment to load the ansible-playbook executable. So we need to ensure Vagrant will find the wrapper executable to hand off to the Cygwin envionment.

Simply copy the ansible-win-wrapper.exe into the same folder of the vagrant.exe and rename it to ansible-playbook.exe.

copy ansible-win-wrapper C:\HashiCorp\Vagrant\bin\ansible-playbook.exe

c:\> vagrant --version
Vagrant 2.0.1

c:\> ansible-playbook --version
  config file = None
  configured module search path = [u'/cygdrive/c/Users/fred/.ansible/plugins/modules', u'/usr/share/ansible/plugins/modules']
  ansible python module location = /usr/lib/python2.7/site-packages/ansible
  executable location = /usr/bin/ansible-playbook
  python version = 2.7.14 (default, Oct 31 2017, 21:12:13) [GCC 6.4.0]

Et voilà, ansible-playbook should now work from vagrant.

Make sure that when you install vagrant plugins to use the command line shell else the ruby gems from your Cygwin environment and from the vagrant embedded msys environment get all mixed up. Check that your Windows command shell PATH variable contains the c:\HashiCorp\Vagrant\bin path for vagrant to work correctly.

Below an example of how to install 2 of the most commonly used plugins.

c:\> vagrant plugin install vagrant-vbguest

c:\> vagrant plugin install vagrant-hostmanager

Fix Vagrant SSH Bug

Some SSH arguments used by ansible playbook shell commands are hardcoded in Vagrant and cannot be overridden by ansible.cfg settings. In particular it will override the control_path = none setting in ansible.cfg with a hardcoded -o ControlMaster=auto shell ssh parameter.

As of 2018 setting up persistent ssh transactions is not possible on Windows. To disable ControlMaster, either comment out line 314 in $VAGRANT_HOME/embedded/gems/gems/vagrant-2.0.1/plugins/provisioners/ansible/provisioner/host.rb or change it to ControlMaster=none or to ControlMaster=no for OpenSSH SSH v7.+ executables.

# which are lost when ANSIBLE_SSH_ARGS is defined.
unless ssh_options.empty?
  ssh_options << "-o ControlMaster=no"
  # DISABLE ssh_options << "-o ControlPersist=60s"
  # Intentionally keep ControlPath undefined to let ansible-playbook
  # automatically sets this option to Ansible default value

Test Example

Setup a Vagrant project folder with a few basic files. I use cygwin terminal for simplicity but you can also do all of this in windows command or powershell.

$ mkdir ~/vagrant-test
$ cd ~/vagrant-test

All 4 files listed below go into the project folder.


A basic Vagrant machine definition with ansible provisioner configuration.

# -*- mode: ruby -*-
# vi: set ft=ruby :
Vagrant.configure(2) do |config| = "hashicorp/precise64"

  config.vm .provision "ansible" do |ansible|
    ansible.verbose = "v"
    ansible.limit = "all"
    ansible.inventory_path = "./inventory"
    ansible.playbook = "playbook.yml"



Ansible default configuration with some Windows specific config.

# default inventory file
inventory = ./inventory

# disable retry
retry_files_enabled = False

# disable host checking
host_key_ckecking = False
record_host_keys = False

# below does not seem to work anymore so adding ssh args as is
ssh_args = -o ControlMaster=no -o UserKnownHostsFile=/dev/null -oStrictHostKeyChecking=no -o IdentitiesOnly=yes

# ControlMaster on cygwin OpenSSH does not work, must disable it
# otherwise ansible will not be able to connect to the target host
# control_path = none


Need to create an ansible inventory definition, the default Vagrant generated one does not work, vagrants ansible provisioner generates a inventory path arg that is Windows but must POSIX for ansible to work properly, so we just cheat a little.

default ansible_ssh_host= ansible_ssh_port=2222 ansible_ssh_user=vagrant ansible_ssh_private_key_file=./.vagrant/machines/default/virtualbox/private_key

Note: You may need to adjust the ansible_ssh_port to whatever the Vagrant machine bound to. You can get around all this by using a DNS plugin like vagrant-hostmanager and then just define actual DNS resolvable vagrant machine names in the inventory.

Also may need to $ chmod 0644 inventory depending on how your cygwin fstab is setup, ansible may complain about +x permissions.


- hosts: all
  - name: Greetings
    debug: msg="Hello Ansible from Vagrant {{ ansible_system }} {{ ansible_distribution }}"
  - name: Whats under the Hood
    command: uname -a

Lets run it:

$ vagrant up --no-provision

Bringing machine 'default' up with 'virtualbox' provider...
==> default: Importing base box 'hashicorp/precise64'...
==> default: Forwarding ports...
    default: 22 (guest) => 2222 (host) (adapter 1)
==> default: Booting VM...
==> default: Waiting for machine to boot. This may take a few minutes...
    default: SSH address:
==> default: Machine booted and ready!
$ vagrant provision
==> default: Running provisioner: ansible...
Windows is not officially supported for the Ansible Control Machine.
Please check
    default: Running ansible-playbook...

PLAY [all] *******************************************************************************************************************************************************************************************************

TASK [Gathering Facts] *******************************************************************************************************************************************************************************************
ok: [default]

TASK [Greetings] *************************************************************************************************************************************************************************************************
ok: [default] => {
    "msg": "Hello Ansible from Vagrant Linux Mandriva"

TASK [Whats under the Hood] **************************************************************************************************************************************************************************************
changed: [default] => {"changed": true, "cmd": ["uname", "-a"], "delta": "0:00:00.001658", "end": "2018-02-04 04:06:48.369022", "rc": 0, "start": "2018-02-04 04:06:48.367364", "stderr": "", "stderr_lines": [], "stdout": "Linux precise64 3.2.0-23-generic #36-Ubuntu SMP Tue Apr 10 20:39:51 UTC 2012 x86_64 x86_64 x86_64 GNU/Linux", "stdout_lines": ["Linux precise64 3.2.0-23-generic #36-Ubuntu SMP Tue Apr 10 20:39:51 UTC 2012 x86_64 x86_64 x86_64 GNU/Linux"]}

PLAY RECAP *******************************************************************************************************************************************************************************************************
default                    : ok=3    changed=1    unreachable=0    failed=0

Random Historic Notes

Installing Crypto Dependencies

There also used to be a problem installing Ansible's dependency pycrypto. If you have an up-to-date version of Cygwin and its packages installed, you are fine. However if there are problems with pycrypto, here 2 options to install it on Cygwin.

Install pycrypto via pip using below compiler flag:

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

or just compile it from sources:

mkdir -p ~/workspaces/python && cd ~/workspaces/python
# download and unpack pycrypto 2.6.1 sources
curl | tar xzvf -

# compile disabling BSD source
cd pycrypto-2.6.1
CFLAGS="-g -O2 -D_BSD_SOURCE" python build build_ext -DMS_WIN64

# install module
python install

Vagrant Ansible Provisioner Bug Fix (version 1.8.x only)

This one is not to be missed, Vagrant does not send extra args in json format properly to ansible on Windows. Some discussion documented here.

Basically when providing any additional playbook parameters as a hash in Vagrant using the extra_args configuration option, this data is not sent in the right format to the ansible playbook.

ansible.extra_vars = {
  my_special_param:{ |n| "#{(1 + n).to_s.rjust(2,'0')}" }


--extra-vars='{ \"my_special_param\":[\"01\",\"02\"] }'



This problem is caused by the way the JSON is generated for a ruby hash.

The first problem is that the generated json does not escape the double quotes which will get lost in the Subprocess call out.

The other problem is that ansible-playbook is very picky in the way it receives and parses the json in the --extra-vars argument. In particular it expects a space after the opening bracket { and a space before the closig bracket }.

What did the trick for me was to apply this hack to the following vagrant file $VAGRANT_HOME/embedded/gems/gems/vagrant-1.8.7/plugins/provisioners/ansible/provisioner/base.rb, obviously this will void your warranty but it works.

def extra_vars_argument
  if has_an_extra_vars_file_argument
    # A JSON or YAML file is referenced.
    # Expected to be a Hash after config validation.
    config.extra_vars.to_json.gsub('{', '{ ').gsub('}', ' }').gsub('"', '\\\"') # << the hacked line fixes space of the curlies and escapes the double quotes
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