Unpacking Software Livestream

Join our monthly Unpacking Software livestream to hear about the latest news, chat and opinion on packaging, software deployment and lifecycle management!

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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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Chocolatey Coding Livestream

Join us for the Chocolatey Coding Livestream, where members of our team dive into the heart of open source development by coding live on various Chocolatey projects. Tune in to witness real-time coding, ask questions, and gain insights into the world of package management. Don't miss this opportunity to engage with our team and contribute to the future of Chocolatey!

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Calling All Chocolatiers! Whipping Up Windows Automation with Chocolatey Central Management

Webinar from
Wednesday, 17 January 2024

We are delighted to announce the release of Chocolatey Central Management v0.12.0, featuring seamless Deployment Plan creation, time-saving duplications, insightful Group Details, an upgraded Dashboard, bug fixes, user interface polishing, and refined documentation. As an added bonus we'll have members of our Solutions Engineering team on-hand to dive into some interesting ways you can leverage the new features available!

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Chocolatey Community Coffee Break

Join the Chocolatey Team as we discuss all things Community, what we do, how you can get involved and answer your Chocolatey questions.

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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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Use Cases


Many IT teams still rely on manual configurations, custom scripts, golden images or outdated tools to manage Windows infrastructure. This results in errors and slow deployments, or worse - unpatched environments that leave you susceptible to security incidents.

From a server point of view you need to ensure a consistent, reliable approach without having manual intervention, and allowing you to run the businesses on the software and having to care, water, and feed the servers. When you get to the world of cloud and containers this is only amplified as you are managing the unknown.

Chocolatey provides a standardized, scalable approach to server management. From setting up a new server, to ensuring critical updates are in place, or supporting a migration project.

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Desktops & Endpoints

Deploying software to desktop and endpoint devices is not always easy, especially in a highly regulated and locked down environments. How do you ensure your teams have the most up to date software deployed to their desktops?

For endpoint users you need to ensure they are productive, efficient, and have no vulnerabilities. So how can you ensure they have the latest software, but at the same time ensure user experience is not compromised?

Chocolatey provides a unique and very cost effective approach to managing your desktop software and can be combined with your existing solutions. Chocolatey for Business (C4B) enables better security and visibility, centralized reporting, and a self-service GUI to allow non-administrators to manage optional software you've approved! Soon C4B will also have endpoint management as part of its Central Management offering.

Cloud / Containers

Deploying to new environments, whether a cloud instance or using containers comes down to eliminating complexity, and making it easier to deliver quality software faster.

When speed is of the essence, how can you begin to easily manage the entire software lifecycle? You need to find solutions that work at the pace of newer technologies, treating your deployments and dependencies as independent building blocks that can be combined in numerous ways.

Chocolatey offers developers a standardized and repeatable approach to deploying Windows software, in both development and production environments. Organizations use Chocolatey in Docker, AWS, and Azure when they need simple, powerful, and flexible solutions to meet the needs of those environments. Chocolatey "packages" are those building blocks, forming the foundation for your deployments.


Most organizations have already invested in tools and solutions across their IT environment. Before adding more tools, IT teams may need to ensure that their existing investments are maximized. Teams also need to ensure they don't get locked in proprietary technologies that don't integrate well in their environments.

Chocolatey maximizes existing knowledge by bringing PowerShell to the forefront and allowing you to leverage existing tools you are already using. Chocolatey has integrations and is used in conjunction with leading and emerging technologies:

  • Configuration Management tools like Puppet, Chef, Ansible, and Powershell DSC
  • Repository solutions such as JFrog Artifactory, Sonatype Nexus, and Inedo ProGet
  • Continuous Integration Servers such as Jenkins, Circle CI, AppVeyor, and TeamCity
  • Source Control providers like GitHub and GitLab
  • Microsoft tools like SCCM and Intune and third party endpoint management solutions like Connectwise Automate, Ivanti, and Altiris

Chocolatey's unique ability to work with any Windows machine, anywhere, allows you to deploy packages easily and efficiently in every environment, from on-premises, to the cloud (Azure, AWS, etc), to Docker containers, through many different tools and technologies.