Chocolatey Community Coffee Break

Join the Chocolatey Team on our regular monthly stream where we discuss all things Community, what we do, how you can get involved and answer your Chocolatey questions.

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Chocolatey Product Spotlight

Join the Chocolatey Team on our regular monthly stream where we put a spotlight on the most recent Chocolatey product releases. You'll have a chance to have your questions answered in a live Ask Me Anything format.

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Announcing Chocolatey Central Management 0.10.0

Livestream from
Thursday, 06 October 2022

We recently released our largest update to Chocolatey Central Management so far. Join Gary and Steph to find out more about Chocolatey Central Management and the new features and fixes we've added to this release.

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Chocolatey and Intune Overview

Webinar Replay from
Wednesday, 30 March 2022

At Chocolatey Software we strive for simple, and teaching others. Let us teach you just how simple it could be to keep your 3rd party applications updated across your devices, all with Intune!

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Chocolatey For Business. In Azure. In One Click.

Livestream from
Thursday, 9 June 2022

Join James and Josh to show you how you can get the Chocolatey For Business recommended infrastructure and workflow, created, in Azure, in around 20 minutes.

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The Future of Chocolatey CLI

Livestream from
Thursday, 04 August 2022

Join Paul and Gary to hear more about the plans for the Chocolatey CLI in the not so distant future. We'll talk about some cool new features, long term asks from Customers and Community and how you can get involved!

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Hacktoberfest Tuesdays 2022

Livestreams from
October 2022

For Hacktoberfest, Chocolatey ran a livestream every Tuesday! Re-watch Cory, James, Gary, and Rain as they share knowledge on how to contribute to open-source projects such as Chocolatey CLI.

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Chocolatey Product Spotlight: Chocolatey 1.2.0 and Chocolatey Licensed Extension 5.0.0

Livestream from
Thursday, 03 November 2022

Join Paul and Gary for this months Chocolatey product livestream where we look at the latest release of Chocolatey 1.2.0, Chocolatey Licensed Extension 5.0.0 and shine a spotlight on the new hook scripts functionality. This opens up so many possibilities for Chocolatey CLI users!

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Chocolatey Coding Livestream

Livestream from
Tuesday, 29 November 2022

Join Josh as he adds the ability to manage Chocolatey GUI config and features with the Chocolatey Ansible Collection.

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Introduction into Chocolatey with Veeam

Webinar from
Tuesday, 13 December 2022

Join Gary, Paul, and Maurice as they introduce and demonstrate how to use Chocolatey! Questions will be answered live in an Ask Me Anything format.

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How Chocolatey Works

Simplify Windows Software Management with Chocolatey


Chocolatey is a software management solution that gives you the freedom to create a simple software package and then deploy it anywhere you have Windows using any of your familiar configuration or system management tools.

If you ever used yum, apt, pacman or indeed any package managers on Linux, or Homebrew on a Mac, you already know what Chocolatey is. Chocolatey is the Windows package manager, in the same way that RPM is a package manager for Linux.

Designed to be simple to use, it provides a suite of powerful features that scale for your existing, and your future infrastructure. Power and flexibility in one simple product, that's Chocolatey.

So whether you are an individual, a small organization, or a large enterprise, Chocolatey provides you with the features to be able to manage your Windows software simply, saving you time and resources. Getting started with Chocolatey is quick and easy - you can start using Open Source for free or contact us for a trial of our commercial edition.

What is Chocolatey
The biggest challenge is reducing duplication of effort, so users turn to Chocolatey for simplicity.

Rob Reynolds, Founder of Chocolatey Software

Deploy Anywhere You Have Windows

We designed Chocolatey to work with the widest range of Windows operating systems all the way back to Windows 7 and Windows Server 2003. We also support cloud environments such as Microsoft Azure, Amazon AWS and any others where Windows platforms are available. Chocolatey runs on Windows Server.Core and Docker Windows container as well.

One product to manage all the software on your entire Windows estate cuts training costs for staff saving both money and time that could be better spent elsewhere within your organization.

Complete Software Coverage

The software environment on Windows is much more than what is shown in Programs and Features. Which is why Chocolatey manages all software on Windows including software installers, scripts, zip files and internal software.

Check out our Architecture Diagram for a better understanding of organizational requirements.

Reliable and Secure

Chocolatey requires no internet access whatsoever. You can build and host packages internally all for free, which gives you complete control over your environment.

Additionally, leverage over 7,000 community packages - internalizing them for use in your environment. This allows you to reuse existing logic that has been tested across multiple environments. Add in automatic internalization using Package Internalizer to take advantage of a hands off approach updating packages within moments of when they are updated in the community!

Use Familiar Tools

Chocolatey packages use PowerShell to drive them so no need to learn another language to deploy software which cuts down the time from installation to package deployment.

You can use Chocolatey to deploy software using the tools you already know. Many configuration management tools such as Ansible, Chef, Puppet, PowerShell DSC, Salt and others have specific support for Chocolatey. Any end point management solution such as SCCM, Altiris, Connectwise Automate or others that allow you to manage remote deployment can use Chocolatey to manage software as well.