user

Should You Invest in a Chocolatey for Business License?

Introduction

Crista Perlton

Crista Perlton


LATEST POSTS

How File Shares for OSS Packages Create More Problems Than They Solve 11th December, 2025

How Pulling OSS Packages Directly Leads to Chaos 09th December, 2025

Chocolatey

Should You Invest in a Chocolatey for Business License?

Posted on .

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

Whether your organization is just looking into Chocolatey or has been using its OSS version for some time you might be wondering if investing in the “Chocolatey for Business” (C4B) license is the way to go for your organization. For those creating many of their own packages and internalizing them, the $17/node fee pays for itself — mostly because of the time it saves. But does it make financial sense if you’re not creating your own packages? 

Chocolatey gives us a detailed breakdown of the differences between licenses, but you may still be asking what difference package builders and internalizers make, as well as what you’re getting out of the included support. 

In this article, we’ll take a closer look at what the “Chocolatey for Business” license offers, helping you figure out if it’s worth it for your organization compared to going with the open-source version.

Note: This will not cover the Chocolatey “Pro” license as it is better suited for individuals rather than the organizations this article caters to. 

🏗 Speed Up your Package Creation 

Are you creating your own packages, or editing existing ones to internalize or privatize them? If so, you’ll need a decent knowledge of PowerShell. On top of this, you’re also looking at time working on the install script and other configurations, and then making sure everything works.

The Package Builder that comes with “Chocolatey for Business” as both GUI and CLI makes the process easier. It turns an .msi or .exe into a Chocolatey package in a few seconds —just right-click, and the package is built and ready to deploy. Larger installers will take longer, but still be done in less than a minute. Compare this to doing it manually, which could take minutes, hours, or even days if you’re not skilled with PowerShell. 

Even if you’re confident with PowerShell, the Package Builder is still faster than running choco new and modifying the install scripts yourself, along with figuring out uninstall steps and other configurations. Once you’ve codified it and run choco install, it will follow the steps according to the script —unlike doing it manually, where you might overlook a step.

⚙ Simplify your Internalization Process 

Whether you’re using the OSS version of Chocolatey or have a “Chocolatey for Business” license, it’s generally recommended to privatize or internalize your packages. “C4B” includes a Package Internalizer that lets you auto-configure packages to be internalized. This again saves time compared to doing it manually. 

The Package Internalizer allows you to bring any of Chocolatey’s 10,000+ packages into your organization’s network and host them in its own repository, giving you full control. The internalization process pre-downloads and rewrites the package to include any necessary binaries. It also reviews the install script to identify any remote resources, and downloads them to a local directory. 

It then edits the install script to use the local resources instead, and recompiles the package. Once the package is in your organization’s internal repository, you won’t need the internet to use it. 

Much like the Package Builder, the main benefit of the Package Internalizer is the time saved. You could internalize manually, but if your organization has a lot of packages this may take anywhere from minutes to hours.  Alternatively, paying for “C4B” gets you an automated solution that reduces the time needed. 

🛠 Get Chocolatey Support When You Need It 

One other thing about the “Chocolatey for Business” license is the support that comes with it. If you’re just starting out with Chocolatey, the “C4B” license includes a four-week trial period. During this trial, Chocolatey support is fully included. The trial begins with a supported onboarding call, helping your organization deploy Chocolatey in its preferred environment. The actual trial period only starts after this call, ensuring you get the full four weeks to experience Chocolatey. 

Once you’re using Chocolatey, anytime you come up against an issue like a problematic package or PowerShell script, Chocolatey’s solutions engineers are on hand to help. They’ll also help with non-Chocolatey issues, like setting up SSL certificates for your repository if you’re not familiar with them. 

I spoke to Chocolatey’s Support Manager, Stephen about their support. “Response time is a big deal—we can usually fix things in about ten minutes.” he told me. “We strive for simple, and are about teaching people to fish.” While you can look up Chocolatey documentation to learn how everything works on your own, the support that comes with a “C4B” license will be there to guide you directly.  

Save Time and Effort with Chocolatey For Business 

The main benefit of “Chocolatey for Business” is the time it saves. For many organizations, this makes it worth the investment in the long run. While you can get similar results with the OSS version, decide if it’s worth spending the extra time creating and internalizing your packages —when the option to simply pay for it exists. The more packages your organization has, the more this matters.

“C4B” also support for onboarding, package creation, and ongoing management, as well as “Chocolatey Central Management” a web-based platform for reporting and deployment. This lets administrators to visualize the state of packages, group machines, and perform package or PowerShell script-based deployments.

It’s about weighing the ease of use against the cost of a “C4B” license to decide the best approach for your organization’s needs.  

That was quite a bit to cover, and it’s best to summarize the key points to revisit when needed. Why not take a look at our free guide Chocolatey for the Enterprise, a handy eBook containing everything from this page to information on versioning, automated deployments, offline environments, and licensing with Chocolatey. Sign up for your free copy today!

Crista Perlton

Crista Perlton

Navigation