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Portable Ansible Installation on Windows 7 using Cygwin


You want to install ansible on Windows 7 x64

Environment Information

  • Windows OS:
        powershell -NoProfile [System.Environment]::OSVersion.Version
        OS: Windows 7 x64
        Major  Minor  Build  Revision
        -----  -----  -----  --------
        6      1      7601   65536
  • Cygwin Version (post-installation): 3.0.7(0.338/5/3)
  • Ansible Environment (post-installation):
      ansible --version
      ansible 2.9.0.dev0
        config file = None
        configured module search path = [u'/home/${USERNAME}/.ansible/plugins/modules', u'/usr/share/ansible/plugins/modules']
        ansible python module location = /usr/lib/python2.7/site-packages/ansible-2.9.0.dev0-py2.7.egg/ansible
        executable location = /opt/ansible/bin/ansible
        python version = 2.7.16 (default, Mar 20 2019, 12:15:19) [GCC 7.4.0]


Install cygwin

  • Download cygwin64 from
  • Create the installation folder (I'm using C:\tools\cygwin)
  • Move setup-x86_64.exe to C:\tools\cygwin
  • Click setup-x86_64.exe
  • Make sure to set the install folder and package folder to C:\tools\cygwin
  • Go through the setup instructions, and when at the package selection screen,
  • Only install wget
  • The cygwin64 core package installations will take time, so busy yourself with something else in the meantime :)
  • Once the installation is complete, close it out

Install python and its dependencies

  • From the installation folder (C:\tools\cygwin), click Cygwin.bat
  • This will initialize your cygwin environment and start the bash interactive terminal
  • Adjust shell environment:
    export PATH="/usr/bin:$PATH"
  • Install the apt-cyg package manager
    chmod +x apt-cyg
    mv apt-cyg /usr/local/bin
    which -a apt-cyg >/dev/null 2>&1 && echo ok
  • install git, python-devel, gcc-g++, curl, dos2unix, zip, unzip
    apt-cyg install git python-devel curl dos2unix zip unzip
  • install pip

Install python and its dependencies

Your cygwin environment should be good for installing ansible, so let's get to it.

  • Install dependence
    apt-cyg install openssl openssl-devel libffi-devel vim
    apt-cyg install python-{jinja2,six,yaml,crypto,cryptography}
  • Install ansible from github
    mkdir /opt
    cd /opt
    git clone --depth 1 git://
    cd ansible
    python install
  • Update your PATH variable
    echo export PATH="/opt/ansible/bin:\$PATH" >> ~/.bash_profile
  • Verify installation
    which -a ansible >/dev/null 2>&1 && echo We found the anible binary! || echo We could not find the ansible binary! Please troubleshoot!
  • Troubleshooting
    If problems, use a search engine to look up any errors, start over, rinse/repeat

Test Run

The below worked!

ansible --connection=local localhost, -m setup -a 'filter=ansible_host*'


Setup cmder

I ran the above tests using Cmder.

Instructions: - Start cmder - Click the green + sign at the bottom right - Click "Setup Tasks" - Click the + sign at the bottom of 'Predefined tasks (command groups)' - For 'Task Parameters', enter:

/icon "**C:\tools\cygwin**\Cygwin.ico"
- Paste this into the empty text area at the bottom right:
-cur_console:t:ansible "**C:\tools\cygwin**\bin\bash.exe" --login -i


Final folder size for C:\tools\cygwin: 1.24 GB

That's a big-ass folder for lil' ol' ansible ...

So yeah ...

Learning Points

Ansible can (at least in theory) run on Windows 7 x64, but it's not without pain AND it's not without problems.

I tested the uri module and was greeted with an error:

The following modules failed to execute: setup
See stdout/stderr for the exact error

More digging I must do.