Step-by-Step Ansible Tutorial for Windows Server 2022: Optimizing WinRM

Join us at ‪@LondonIAC‬ in this hands-on (semi-realtime) tutorial where we dive straight into using Ansible with Windows Server 2022 over WinRM.

Please like and let me know it worked for you (or what issues you faced) in the comments!

* For SSH (port :22) connectivity between Ansible and Windows follow my other tutorial here:    • Use Ansible to Manage Windows Servers...  

We start by creating a Windows Server 2022 on AWS. Then, we configure WinRM on the server using a set of efficient commands. Next, we establish an Ansible-to-Windows connection via WinRM.

We verify the setup's success with the win_ping module to confirm connectivity and authentication. Finally, we execute a simple Ansible playbook to create a directory and file that includes an Ansible fact.

This tutorial is a straightforward guide to setting up and running Ansible for Windows Server 2022 via WinRM. Whether you're an experienced IT expert or a beginner, this tutorial provides a clear roadmap to get you started.

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PowerShell commands (AWS specific but you can adjust to your own requirements):

Enable PowerShell remoting
Enable-PSRemoting -Force

Set WinRM service startup type to automatic
Set-Service WinRM -StartupType 'Automatic'

Configure WinRM Service
Set-Item -Path WSMan:\localhost\Service\Auth\Certificate -Value $true
Set-Item -Path 'WSMan:\localhost\Service\AllowUnencrypted' -Value $true
Set-Item -Path 'WSMan:\localhost\Service\Auth\Basic' -Value $true
Set-Item -Path 'WSMan:\localhost\Service\Auth\CredSSP' -Value $true

Create a self-signed certificate and set up an HTTPS listener
$cert = New-SelfSignedCertificate -DnsName $(Invoke-RestMethod -Uri http://169.254.169.254/latest/meta-data/public-hostname) -CertStoreLocation "cert:\LocalMachine\My"
winrm create winrm/config/Listener?Address=*+Transport=HTTPS "@{Hostname=`"$(Invoke-RestMethod -Uri http://169.254.169.254/latest/meta-data/public-hostname)`";CertificateThumbprint=`"$($cert.Thumbprint)`"}"

Create a firewall rule to allow WinRM HTTPS inbound
New-NetFirewallRule -DisplayName "Allow WinRM HTTPS" -Direction Inbound -LocalPort 5986 -Protocol TCP -Action Allow

Configure TrustedHosts
Set-Item WSMan:\localhost\Client\TrustedHosts -Value "*" -Force

Set LocalAccountTokenFilterPolicy
New-ItemProperty -Name LocalAccountTokenFilterPolicy -Path HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Policies\System -PropertyType DWord -Value 1 -Force

Set Execution Policy to Unrestricted
Set-ExecutionPolicy Unrestricted -Force

Restart the WinRM service
Restart-Service WinRM

List the WinRM listeners
winrm enumerate winrm/config/Listener
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#ansible #windows #winrm