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Step-by-step guides for all things Chocolatey! Earn badges as you learn through interactive digital courses.

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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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Simplifying Chocolatey Setup: Have it Your Way

Webinar Replay from
Thursday, 02 September 2021

We've been hard at work simplifying the setup of Chocolatey for Business (C4B) for our users. Whether you'd like to "Bring Your Own VM", or spin up a Cloud-ready solution, we've got you covered!

Learn More Watch On-Demand
12 Days of Chocolatey

Event from
December 1 - December 16 2020

The 12 Days of Chocolatey livestream event may be over, but we've archived all the videos for you to watch again!

Watch On-Demand
Chocolatey for Business Feature Video Series

Chocolatey for Business Feature Video Series

In this video series, come take a tour of the many features available in our Chocolatey for Business offering. Many organizations choose Chocolatey for Business when they want to scale out their solution across thousands of nodes, deploy rapidly and reliably every time, mitigate risks with a greatly-simplified patching workflow, and access a Support Team that will guide you on your automation journey.

Watch the Series
Accelerate Automation of Windows with Ansible + Chocolatey

Webinar Replay from
Thursday, 10 December 2020

Together, Ansible and Chocolatey bring faster and more secure deployments to your Windows environments. Use Chocolatey for software/package management and Ansible to automate and guarantee the desired state of your Windows infrastructure, allowing your team to securely deploy applications faster than ever.

Learn More Watch On-Demand
Announcing 11 Years of Chocolatey

Announcing 11 Years of Chocolatey

Read the Blog
Find It, Add It, Install It with Script Builder

Livestream from
Thursday, 7 April 2022

Script Builder allows you to bulk install Chocolatey packages in just a few clicks. Just add packages to Script Builder and choose your integration method to get started!

Watch On-Demand
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!

Watch On-Demand
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.

Watch On-Demand
Unboxing The Third Major Release of Boxstarter

Livestream from
Thursday, 14 July 2022

Boxstarter version 3.0 marks the beginning of a new era of Boxstarter and Chocolatey. Join Gary, Paul, and Manfred as they unbox the best features of Boxstarter.

Watch On-Demand
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!

Watch On-Demand
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