This article is part of a series on Chocolatey for the Enterprise, also available as a chapter in our free, downloadable eBook

Whether you’ve been using Chocolatey in your organization for a while or are just starting out, there are some best practices you can follow to get the most out of it. Chocolatey already makes deploying and maintaining software a breeze, but there are still additional steps you can take to make it a better fit for your organization.

It’s not just about the initial setup —keeping things running smoothly and securely over time is important. Privatizing and internalizing packages helps you control software distribution. Plus, if you’re in an offline or air-gapped environment, you’ll need to set up Chocolatey to work without internet access.

In this article, we’ll walk you through the best ways to integrate Chocolatey into your enterprise environment, from setting up secure repositories to automating software updates and staying compliant.

Best Practices: Chocolatey Environment

Chocolatey is a package manager made to simplify the installation and configuration of software on Windows systems. Using Chocolatey, organizations can distribute software across thousands of Windows desktops. This will make sure machines are running the same software version.

⭐Privatize and Internalize Your Packages

In the enterprise, maintaining security and control over software distribution is vital. For this reason, it is generally recommended to privatize and internalize your organization’s Chocolatey packages. This includes creating and maintaining your own repositories, helping you mitigate the risks associated with community packages before rolling them out in your organization.

⭐ Consider Setting up Chocolatey in an Offline Environment

Another reason to internalize packages is that many organizations operate in closed or air-gapped environments. This poses a challenge when using Chocolatey, as its packages refer to online resources and require internet access. You can get around this in an offline environment by setting up a private repository and internalizing packages. This will allow you to leverage Chocolatey packages without internet access.

Best Practices: Chocolatey Packages

Using Chocolatey effectively requires familiarity with how its packages work. This isn’t just a case of how they are created. It’s also how they are versioned, how licenses work and how you can ensure that they are safe for your organization.

⭐ Align Package and Software Versions

Chocolatey packages at face value seem similar to other packages like NuGet and npm. They have different versions which can be pretty confusing as the version format can vary from package to package. The versions themselves are determined by the package author and in many cases can be different from the software version that they are used to install. For your organization’s own packages, this confusion can be avoided by following some best practices.

⭐ Carefully Review Community Package Licenses

Like their versions, licenses for Chocolatey packages can be confusing. Chocolatey doesn’t enforce software licenses, leaving it up to the organization to make sure any software used is compliant. Script licenses can be ambiguous, and package license URLs may be outdated or incorrect. When dealing with self-service software installations, there’s a risk of unintentional license violations. This issue can be avoided by controlling package use through approval workflows.

⭐Manage Virus Detections with a Private Repository

As Chocolatey packages install and configure actual software, it’s important to understand how to mitigate the risks associated with potential software viruses. Chocolatey integrates with VirusTotal to scan packages against multiple antivirus engines on its servers, flagging files that may be potentially malicious based on multiple detections.

Taking your own precautions is also important. Integrating Chocolatey with a private repository improves virus management. It allows for detailed assessments and better control, even though true malware in packages is rare.

Best Practice: Consider Paid Support

Whether your organization is just starting with Chocolatey or already using its open-source version, it’ll need to decide if the “Chocolatey for Business” (C4B) license is worth it. The C4B license saves time with additional tools and support that aren’t available in the open-source version, especially when it comes to creating and internalizing packages.

However, the value of the C4B license largely depends on your knowledge of PowerShell and how much time you’ll save automating the creation and internalization of packages.

Maximizing Chocolatey in Your Organization

Chocolatey can be beneficial for managing software across tons of Windows machines in your organization. It helps you streamline installation and updates, and by privatizing and internalizing packages, you can keep things secure and under control.

Whether you’re dealing with package versioning, licenses, or virus scanning, building a strong understanding of how Chocolatey works will help you get the most out of it in your organization.

That was a lot of Chocolatey info, and I recommend saving it somewhere nearby for easy access! A better idea would be grabbing a copy of our free eBook Chocolatey for the Enterprise, which expands on the content of these articles and is a great guide for using Chocolatey best practices in your organization. Download your free copy today!