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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Why Chocolatey?

Deploying software can be repetitive, complex, and error-prone. What if you could quickly solve these issues and spend more time on high value tasks?

The Problem


We often hear that managing Windows software can be a frustrating or time-consuming experience. In addition, teams may have some automated approaches, but have identified gaps in the experience. Newer automation approaches (DevOps) and configuration management tools still don't fully address Windows software management in an easy and maintainable way.

Some of the common challenges include:

  • TIME: Manual approach to software deployment is time consuming & inefficient
  • COMPLEXITY: Traditional tools are complex & ineffective in today's IT environment
  • COST: Deploying & managing Windows software without standard package management results in additional overheads

With the ongoing confusion on where do you start? What is the best approach?

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

Rob Reynolds, Founder of Chocolatey Software

> choco install docker-desktop

Simplify Complex Processes, Save Time & Effort


There are a lot of different installer formats and multiple approaches to deploying Windows software. Deploying software without package management on Windows can be complicated and time-consuming.

System engineers can spend hours deploying and configuring Windows software manually. Traditional tools were not built for modern automation and a DevOps approach, which can make achieving consistency and gaining insights across your environment difficult.

Chocolatey simplifies this through simple, repeatable, and automated approach, by using a universal packaging format for managing all aspects of Windows software. Whether you are managing native installers, zips, script, runtime binaries or in-house developed applications, Chocolatey treats them all as 1st class citizens and gives you a consistent, unified approach to software management!

Write Once, Deploy Anywhere, with Anything, and then Simply Track & Manage


Chocolatey aims to automate the entire software lifecycle from install through upgrade and removal on Windows operating systems. We aim to simplify complex processes through a single unifying interface allowing you to control the chaos.

Chocolatey for Business allows organizations to adopt a DevOps approach that can easily manage your Windows environment, delivering applications to servers and end-users faster and more reliably. By taking advantage of PowerShell to provide automated software management instructions, Chocolatey’s built-in functions turn complex tasks into one-line function calls.

Upgrade Steps

Next Steps


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