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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The Best Software Management for Windows Endpoints

Chocolatey Central Management Deployments

Central Management Deployments for Windows Systems Administrators is easy to use yet powerful software for the management of all software on all Windows endpoints

When you have more than one endpoint to manage.. perhaps in more than one location… and the list of software to manage is growing, with patches and releases becoming more frequent… that’s when Sys Admins turn to Central Management Deployments to get a grip of their Windows estate.

"How I Completely Automated Managing Windows Desktop we internalize, schedule and upgrade all of our software with very little human interaction necessary."

Dan Franciscus

Dan Franciscus

Systems Engineer, Institute for Advanced Study


Ready to go!

Simple, sensible, sane!

Everything is set up to work out of the box with convention over configuration. It’s not like starting with an empty Excel spreadsheet! Sensible defaults are preset by experts and it’s ready to go. Connect your repository of packages and your target endpoints then start to build plans for remediation.

Anyone can use it!

Popular and standardized

Deployments uses the ubiquitous Chocolatey packages which have passed a billion installs around the world. You use community packages or curate your own in a private repository. Even the most complex Windows environments and be tamed with the mix of Chocolatey packages and Deployments automation and control.

Keeps finance happy

Budget friendly

Deployments is one feature of the larger Chocolatey for Business suite, which has a list price starting at $16.50 for each managed target. But you get more features that integrate with Deployments and further improve your workflow. Other parts of C4B include Visual Package Management (Internalizer, Synchronizer and more) and Self-Service Anywhere so users can “pull” packages as an alternative to Deployments “push”.

Plays nice with others

Integrates with everything

You can use Deployments on its own, but in more complex environments you can plug Deployments into a larger workflow and other tools. For example, you can easily integrate Deployments with a software repository of your choice, and also with configuration management tools such as Puppet, Ansible and Microsoft SCCM.

Pre-Deployments pain-points

We hear common complaints from our community about Windows software management —
do you feel this pain?

I'm flying blind

I can't manage what I can't see or understand. Before Central Management Deployments I found it hard to see (a) what packages exist in the library and (b) which of those packages are deployed to which endpoints and (c) which packages are out of date and need remediation.

Automation is hard

We have a reasonably complicated landscape. Manual tools and processes need more time and budget to make them work. New hires struggle to get up to speed, everyone is making mistakes, tickets queue gets longer, users get frustrated. Short cuts are taken. I'm exhausted.

We're in a mess!

Over time we've accrued a bunch of tools and a mix of manual and automated steps: we've built a Heath Robinson contraption! We need to simplify it all to focus on what's important: getting Windows packages to Windows endpoints on time.

How it works

Deployments is the new Sys Admin on your team that always does as it’s told and never sleeps!

Integrate into your existing setup, or create a new and improved software management system.
  • Connect Deployments to your software repository.
  • If you need to use other tools like Configuration Management, integrate with those.
  • Integrate Deployments with your endpoints.
Create a WinOps workflow like the popular OODA loop:
  • Observe - see new software, releases, upgrades and patches.
  • Orient - which software is out of date on which endpoints?
  • Decide - build plans to automate software management.
  • Act - on-demand execute or schedule plans.


All the power without the learning curve means Sys Admins can go from zero to hero in hours. Create a modern software management workflow that’s aligned with WinOps, DevOps and OODA.

Observe & Orient

  • Dashboard
  • Reports
  • Software Collections
  • Target Groups
  • Watch plans execute
  • View endpoint logs


  • Create Plans
  • Enrich with Powershell
  • Ordered, multi-step plans
  • Each step can target different endpoints with different packages
  • Fine-grained permissions


  • On-demand immediate action
  • Schedule out-of-hours, unattended
  • Live display to watch plans execute
  • Integrate with other systems live
  • Powershell expert control

What Sys Admins say about Central Management Deployments

I can arrange my important software into collections and my endpoints into groups by department. Then I can see which departments have out of date software and who are exposed to a new CVE.

Some endpoints need different packages and have dependencies in the same change plan. I can now set the order to upgrade dependencies first, pause services while software is updated. It's automating how I used to carefully do it by hand.

With the visibility on the dashboard, reports and plans, I can communicate changes better to the IT Service Management team. It gives me confidence that everyone knows what's happening so if there is a problem, we're covered!

Getting Started

An expert explains Central Management Deployments
A Windows Automation Expert explains Central Management Deployments