Windows Automation: Comparing Methods & Tools for Automating Windows Infrastructure

Finding the right automation tool for Windows environments can be frustrating. Legacy systems, a GUI-centric design, and proprietary tooling are a few of the reasons Windows automation can be challenging — especially in environments where Windows isn’t the only OS.  

Many organizations struggle to choose tools that will let them automate Windows infrastructure without contributing to tool sprawl. With various Microsoft native solutions and open source alternatives readily available, how do you know which tool is best for your needs?

In this post, I’ll offer the pros and cons of various automation methods in a Windows ecosystem. I’ll also share my experience with Windows infrastructure automation to offer advice and tips on managing configurations across multi-OS fleets or multiple versions of Windows.

How to Automate Windows

To automate Windows desktops, servers, and other Windows infrastructure, you need to use automation scripts and tools like Chocolatey, SCCM, and Puppet. With Windows automation, you can configure user accounts and group policies, automate software deployment, automate patching, and automate server provisioning.

If you're automating simple things on Windows, like installing software or adjusting DNS configurations, simple tools like Task Scheduler and Power Automate should suffice. But if you've read this far, I'm assuming you're interested in automating a lot of machines that run Windows simultaneously.

In that case, automation is far too complex a process for one tool or piece of software to handle it all for you. Automating Windows (or any OS) requires an automation strategy, which typically includes:

1. Defining goals, scope, and constraints
2. Choosing an automation tool (which come in agent-based and agentless varieties, as well as Windows-specific or cross-platform options)
3. Setting up prerequisite communication protocols and permissions
4. Writing automation scripts and configurations with PowerShell or a configuration management tool
5. Testing your automation scripts and configurations on isolated systems
6. Rolling out automations gradually and monitoring their impact
7. Monitoring, auditing, iterating, and improving automations across your Windows environments

Why Windows Automation Can Be Frustrating

Automating Windows infrastructure can be challenging because it often means managing legacy OSes and applications using proprietary software. Unlike Linux automation, Windows automation is largely built around graphical user interfaces, making Windows a bit harder to manage as part of a diverse IT system.  

Windows is Built Around a Graphical User Interface (GUI)

Linux and other Unix-like OSes are designed for modularity and automation, with a command-line interface (CLI) that makes scripting fairly straightforward. Windows, on the other hand, was built to prioritize the user experience so Microsoft adopted a graphical user interface (GUI) to make the operating system more inviting.

Though Windows has incorporated CLI and automation through tools like PowerShell (more on that later), its GUI-first design makes automation a secondary consideration on Windows. CLI is fairly standard across *nix OSes, leaving Windows on its own until more recent versions of PowerShell (which are now cross-platform).

Windows Automation Often Relies on Proprietary Tools

Specifically on Windows, automating often means managing various OS versions and applications using proprietary software. Windows automation historically has had you vendor locked: Microsoft creates the OS, so you’re forced to use Microsoft tools to manage things like automation and configuration on that OS.

Looking for more tools to manage configurations on Windows? Read our blog for a list and our recommendations for Windows configuration management >> 

If you’re a Windows-only shop, you might not think twice about using Microsoft products to manage Microsoft operating systems. But if Windows is just one of the OSes you manage, that list of available tools that are cross platform gets much smaller and more limited.  

Group Policy management, Microsoft Configuration Manager, and native Windows PowerShell (v5.1) are not much good outside of the platform they’re built for. While Azure Automanage and later versions of PowerShell have cross-platform capabilities, they’re newer to the automation scene and come with some limitations (more below). And, of course, all of the above tools can leave you vendor-locked to Microsoft’s ecosystem.

Windows Infrastructure Automation Tools: Your Main Methods & Options

Common Windows-native infrastructure automation tools include PowerShell, Microsoft Configuration Manager, and Active Directory - Group Policy Management. Non-Microsoft options include agentless (like Ansible) and agent-based automation tools (like Puppet).

When it comes to Windows configuration management, there are several methods, including agentless and agent-based tools. Each of these types of tools comes with their own pros and cons, so rather than a “which is better?” comparison, and it’s best to use the one that best fits your organization’s specific needs.

Here is a comparison table of several tools we’ve found can help you meet your organization’s challenges for automating Windows infrastructure. 

So, Which Windows Automation Tool Should You Choose?

As mentioned above, it’s better to take stock of your organization’s specific needs and choose an automation tool from there, rather than trying to find a ‘magic bullet’ automation tool.

That said, there are a few general use cases and factors that can make one method or tool more practical than another for Windows infrastructure automation.

Here’s what I’d recommend for three common setups:

• Organizations managing only Windows servers in Azure
• Organizations managing Windows and *nix OSes across multiple cloud providers
• Organizations managing servers running multiple OSes in a private cloud environment

Use Case: Automating Windows Servers in Azure

If your scope is exclusively Windows servers and your organization already has a presence in Azure, Azure Automanage could fulfill your needs. It’s integrated deeply with Microsoft’s ecosystem, so features like automated VM configuration management and backups are tailored specifically for Azure.

Note: Virtual machines outside of Azure require Azure Arc, which is a separate paid product.

Use Case: Automating Windows Servers Alongside Linux Distros Across Multiple Clouds

In this case, I would advise a provider-agnostic automation tool (like an open source option) as you want to be able to support your various environments in a consistent way.

When your tools aren’t tethered to a single cloud provider (like Azure, AWS, or Google Cloud Platform), your automation strategy can be more resilient to changes the provider makes to the platform. That helps you maintain better, more complex automation and consistent operations as your infrastructure continues to evolve.

Agent-based tools that support your required operating systems — like Puppet, Ansible, and Chef — could be a great choice!

Use Case: Automating Windows Servers in a Mixed Private Cloud Environment

In this case, I think either an agentless or agent-based tool could be a good fit (depending on your organization's requirements).

Agentless tools can often be set up faster since they don’t require additional installation or configuration of an automation agent, making them more attractive to organizations that need quick deployment.

Agent-based tools, on the other hand, give you more granular control over configurations and enable desired state automation that doesn’t rely on network connectivity, making them generally better for environments with strict security and compliance requirements.

To get a little more specific:

• If data transport is a concern in your mixed-OS, private cloud environment due to security and compliance reasons, an agent-based solution could be just what you need.
• If data transport isn’t a major concern, an agentless solution can provide a low barrier of entry and quick time to value.

How Open Source Software Can Help Automate Your Windows Infrastructure

Like I said above, Microsoft tools aren’t your only option for automating in a Windows environment. Depending on the specifics of your setup, you might use a combination of proprietary tools and third-party offerings, including open source automation tools.

Why Choose Open Source Tools for Windows Automation?

When infrastructure and DevOps teams choose open source software (OSS) to automate tasks, configurations, and workflows, it usually comes down to cost, innovation, and customizability.

The 2024 State of Open Source Report from OpenLogic identified the top reasons organizations choose OSS, regardless of their operating system:

• No License Cost/Overall Cost Reduction (36.64%)
• Functionality Available to Improve Development Velocity (30.71%)
• Stable Technology with Community Long-Term Support (27.64%)
• Access to Innovations and Latest Technologies (26.86%)
• To Reduce Vendor Lock-In (21.29%)

Open Source Tools to Automate Windows Infrastructure

Open Source Puppet

Open Source Puppet is the freely available open source version of Puppet’s configuration management platform.

With Open Source Puppet, you can automate your infrastructure as code to define desired system state, including user accounts and security settings. Open Source Puppet works across cloud, hybrid, and physical deployments, and thousands of modules on the Forge help you configure setups, automate tasks, and ensure Windows security alongside Linux OS security.

Download Open Source Puppet

Puppet Enterprise

The paid enterprise version of Puppet is built on the same open source code as Open Source Puppet, with integrations and extensions to meet the specific needs of your Windows and multi-OS infrastructure.

Puppet Enterprise takes the policy-as-code (PaC) capabilities of Puppet's open source version and adds features, dashboards, and integrations that make it easier to manage infrastructure anywhere at scale so your team can focus on bigger things that drive business value. Try or demo Puppet Enterprise for yourself here.

• Security Compliance Enforcement, available for both Open Source Puppet and Puppet Enterprise, is a Puppet module that uses Puppet code to automatically fix drift for compliance. The sce_windows module on the Forge keeps your Puppet-managed Windows infrastructure in compliance with CIS Benchmarks and DISA STIGs, with customizable features to maintain compliance with other frameworks and regulations. Learn more about Security Compliance Enforcement here.

Bolt

Bolt is a free, agentless automation tool built to complement Puppet’s agent-based automation leveraging modules and tasks.

It can utilize WinRM for, as one Redditor put it, “basically the Windows equivalent of SSH for remote shell-based management without having to launch a full RDP session.” Learn more about Puppet Bolt.

Real Examples of Puppet Automation for Windows

Puppet can be used to automate and manage across large-scale Windows systems as well as mixed IT environments.

The Puppet agent installed on each server or node checks in via HTTPS every 30 minutes — 48 times per day — to make sure its configurations align with the infrastructure as code (IaC) configurations on the primary server. If anything’s out of policy, the agent requests new code from the primary server, which deploys it automatically to bring it back in line.

Hundreds of companies and teams — from Windows-only shops to those running a mix of Windows and Linux — have deployed Puppet to manage Windows at scale, from dozens to hundreds to thousands of machines. Here are a few.

WTW

Willis Towers Watson (WTW) is a British-American consultancy and support company for insurance, pensions, retirement planning, and more. The infrastructure for the company’s Insurance Consulting and Technology business is exclusively hosted on Azure and running Windows. Lead DevOps Engineer Darren Gipson’s team chose Puppet to provide common tooling for consistency, security, and cost savings in its VM deployment. He describes Puppet as “a massive win” for his infrastructure, team, and company.

Read the WTW case study >>

Swiss Re

John Rogers, System Engineer at reinsurance provider Swiss Re, used to need weeks to stand up Windows machines using tools like SCCM, PowerShell DSC, and GPOs. So when they needed to move to a new version of Windows, he says, “We thought, ‘This isn’t very agile.’” Now they run end-to-end automation with Puppet, managing 5,800 Unix and Windows servers simultaneously.

Read the Swiss Re case study >>

Tech Manufacturing Company

At his company, Systems Administrator Alex Harden’s team chose Puppet specifically because it can use the same Puppet agent to automate across Windows, Linux, and other Unix environments. “Using Puppet code, we can describe the desired state of the system,” Harden says, “and any adjustments we have to make, we make to the code that’s managing the systems. We can ensure they continue to stay in compliance — not just for that system, but for future systems.”

Read the tech manufacturing case study >>

Is Puppet Right for Your Windows Automation?

Puppet can automate on Windows better than any agentless tool, especially at scale. Organizations around the world use Puppet to reduce manual work as well as modernize, standardize, and control Windows environments across cloud, on-prem, and hybrid.

With agent-based capabilities and modules purpose-built for Windows automation, Puppet makes the impossible possible for teams managing Windows. Learn more on our Automate Windows Infrastructure With Puppet use case page or request a demo of Puppet with our team today.

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