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.

Watch The Replays
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 for Business

Automate your entire Windows Software Lifecycle

Automate software install, upgrade, and removal.

Accelerate rollout and simplify software management.

Reduce time spent on software management by 90%.

Simplify Complex Processes

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.

Chocolatey simplifies this through simple, repeatable, and automated approach, by using a universal packaging format for managing all Windows software. Regardless if installers are; native, zips, scripts, binaries or in-house developed - Chocolatey treats them as all 1st class citizens.

Write once, deploy anywhere, with anything, and then simply track & manage.

Save Time & Effort

System engineers can spend hours deploying & configuring Windows software manually. Traditional tools are just not built for modern automation and a DevOps approach. Gaining insights and consistency across your environment is not always easy.

Chocolatey for Business (C4B) has helped hundreds of system admins save time, reduce downtime, and accelerate deployments.

Chocolatey for Business (C4B) is Complete Software Management. Built on our popular open source offering.

Focused on three value-added areas; improved security, enhanced productivity features, and enabling more visibility. All backed with dedicated support, services, & roadmap

  • Closely aligned to organizational use cases - rapid deployment & highly scalable
  • More visual interfaces (GUIs) & smoother user experience
  • Special advanced functionality i.e Package Creation, Package Internalizer, Package Audit, Package Synchronizer, Self-Service Installer
  • Easy migration path from open source
  • Deep integration with leading technologies

Businesses Trust Chocolatey Software

Many organizations face the ongoing challenge of deploying and supporting various versions of software. Chocolatey allows organizations to automate and simplify the management of their complex Windows environments. Our customers have experienced a massive reduction in effort, improved speed of deployment, high reliability, and comprehensive reporting.

Package Builder

Generate Software Deployment Packages in Seconds

  • Creating packages manually is time-consuming, error-prone, and inconsistent
  • Package Builder automatically creates high-quality packages from an installer/zip in seconds
  • Determining silent arguments based on installer type, with complete customization
  • Supports exe, msi, 7z, zip, msu, and msp files
Chocolatey for Business Package Builder Part: 1
Chocolatey for Business Package Builder Part: 2

Convert Community Packages to 100% Offline & Reliable Use

  • Chocolatey community offers over 7,500 packages; however, those packages require external sources for software binaries from vendor servers at runtime
  • Take advantage of thousands of existing packages without reliance on the Internet
  • Package Internalizer downloads an existing package and all remote resources, and recompiles package to use those resources internally
  • Offers the ability for you to host packages on private internal repositories
Chocolatey for Business Package Internalizer Part: 1
Chocolatey for Business Package Internalizer Part: 2

Real-Time Insights

  • Getting a real-time snapshot of packages and deployments is not always easy
  • With CCM you can bring software visibility to the organizational level
  • Quickly see all software packages across the organization and see what needs attention immediately
  • Generate reporting from views in PDF and Excel format
  • Deployments enable teams to securely manage endpoints w/PowerShell scripts and states of Chocolatey packages directly. The CCM web interface helps with easy set-up, management, and reporting on deployments to endpoints.
Chocolatey for Business - Chocolatey Central Management

Empower Your User Base While Maintaining Security Policies

  • Ensuring software is deployed and updated to users with no ‘admin rights’, or in highly regulated locked-down environments, is a challenge
  • C4B provides organizations the power to easily offer their users an interface to install and upgrade software
  • Offering a user-friendly, consistent, reliable approach without the need for manual intervention
  • C4B installation is completely locked down so non-administrators cannot make changes to configurations. Attempted abuses can be logged and audited.
  • Ability to customize with company logo
Chocolatey for Business Self-Service and Chocolatey GUI Part: 1
Chocolatey for Business Self-Service and Chocolatey GUI Part: 2

Improve Accuracy & Simplify Software Management

  • Gaining visibility beyond just the software ‘installed’ in Programs & Features can be very difficult
  • C4B easily brings all software in Programs and Features under Chocolatey management
  • Package Synchronizer ensures accurate inventory and enables easier management of complex Windows systems
  • Auto-synchronization allows you to uninstall directly from Programs and Features, as it detects when changes have occurred outside of Chocolatey (ie Programs & Features), and updates the Chocolatey package inventory accordingly
  • Track versions of zip archives & your own internal software that is not traditionally visible in system installation
  • Sync command brings all software on a system under Chocolatey management, allowing you to manage upgrades more consistently
  • Show all packages (even those without native installations) in Programs and Features, allowing you to capitalize on existing legacy inventory reporting systems
Chocolatey for Business - Package Synchronizer

Inventory - Comprehensive Software Audit

  • Gain insights on what was installed, by whom, and when
  • Easily identify Out-of-Date Software
  • Identify package upgrades to target on next scheduled maintenance window

Automatically Optimize Your Deployments

  • Package Reducer helps to ensure the space that Chocolatey uses on a system stays minimal
  • Automatic self clean-up after package installation
  • Substantial package size reduction to enable to reduce footprint on endpoints


100 - 499 Machines


/license per year


500+ Machines


/license per year

Enterprise 2000+ Machines

Education & Non-Profits - Special pricing options