install ansible on windows server 2019

Add a new inbound rule to your ... sudo apt-get -y install python-pip python3-pip python-dev libffi-dev libssl-dev sudo pip install ansible...

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How to Install Ansible on Windows: 3 Methods

December 9, 2025 - This tutorial covers different ways to install Ansible on Windows. ... A machine running Windows. A user account with administrator privileges. Windows Subsystem for Linux (WSL) allows users to install different Linux distributions (such as Ubuntu) and use Linux apps and Bash command-line tools directly. This method does not require a virtual machine or dual-boot setup. Install Ansible with WSL by following the steps below:

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SQL Express Setup via WinRM

The SQL Server installer uses DPAPI to encrypt/decrypt data for the installation and typically in WinRM that is unavailable. There are a few ways around this; Use become on the task and that will run the process as the user you specify and can access their DPAPI functions name: run win_package with become win_package: ... become: yes become_method: runas vars: ansible_become_user: '{{ ansible_user }}' ansible_become_pass: '{{ ansible_password }}' Connect with CredSSP authentication over WinRM by setting ansible_winrm_transport: credssp Run the SQL installer using something like psexec with explicit credentials The first is the easiest as it will just work out of the box regardless of transport you are using to connect to the Windows hoset. The 2nd is an option if you have enabled CredSSP auth on the server. The final option really should be avoided as you loose out the benefits of running modules in Ansible and have to handle the idempotency yourself. More on reddit.com

r/ansible

February 2, 2020

Ansible for Windows - Openssh or WinRM?

If your machines already have WinRM configured, just use that. It works fine. One thing about OpenSSH is that I do not believe that it is natively available in the Windows Server OS until Server 2019. You can install it from GitHub on older versions of Windows, but the last time I tested that, it did not appear that the repo was updated very often, and it is not really supported by MS. However, it worked perfectly fine. More on reddit.com

r/ansible

February 28, 2023

Looking for CIS playbook For Windows Server 2019

There are some Googled resources, such as https://github.com/vijayram0690/ansible-cis-hardening-windows but from what I can tell most are not up to date. It might be a good place to start for developing your own, however. ( removed DISA STIG link - my mistake, that was Windows Chef content, not Ansible!) Good news is, if you create more up to date content, you could push it to GitHub or Gitlab for someone else in the community to use! To be honest, there’s a lot of work on compliance standards in bash and Ansible in the Compliance as Code project for Linux, but almost nothing for other platforms. More on reddit.com

r/ansible

December 1, 2020

Using Ansible for Bare Metal Windows Deployments

The cool thing about Server 2012 R2 and newer OS' is that WinRM/PowerShell Remoting is enabled by default and works out of the box with Ansible. This allows you do very minimal work to get Windows installed and then start configuring it straight away with Ansible.

You may also be interested in https://docs.ansible.com/ansible/devel/modules/psexec_module.html. It allows you to run commands on a Windows host using SMB/RPC and can be used to bootstrap older servers to a point where WinRM is ready and available.

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