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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Holiday Holly

12 Days - 1 Topic, 1 Hour, Each Day

Follow along with this video series to relive the 12 Days of Chocolatey livestream event (aka Chocolatey Fest 2020)! You'll learn about the Quick Deployment Environment (QDE), the Choco CCM Module, Self-Service Anywhere, and hear many other exciting new announcements from the Chocolatey team!

  • Chocolatey Central Management Deployments
  • Chocolatey & Ansible
  • Building Packages
  • Self-Service Anywhere
  • NEW exciting Chocolatey announcements
Holiday Holly

Event Replay Archive

Keynote - "The Power of Simple"

Livestream
Speaker: Rob Reynolds

Join us as Rob talks about the elegance and power of simple to kick off the 12 Days of Chocolatey. This session may feel a bit more formal than the other days. We'll be making at least one exciting announcement at the end!

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Redefining Chocolatey

Livestream
Speakers: Rob Reynolds, Adil Leghari

You likely have a picture in your mind of what Chocolatey is to you. Come prepared to have your mind blown.

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Chocolatey Central Managements Deployments Scheduling, Semi-Connected Environments, and API

Webinar
Speakers: Gary Ewan Park, Rain Sallow

Chocolatey Central Management's premiere feature of Deployments now can work with schedules, semi-connected environments, and CCM (Chocolatey Central Management) overall has a published API so you can accomplish more, much more. Separate Registration Required!

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Chocolatey in the Organization

Livestream
Speakers: Gary Ewan Park

Come discover the best practices for setting up and configuring Chocolatey in an Organization. We’ll show you how to better leverage the Chocolatey Community Repository for packages updates, as well as take advantage of the new functionality offered in Chocolatey for Business.

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Building Packages (Open Source and C4B)

Livestream
Speakers: Adil Leghari, Stephen Valdinger

Building Chocolatey packages from scratch can take time and effort. We’ll show you some tips and tricks to help get you started, and then show off the “Easy Button” with Package Builder (a Chocolatey for Business feature).

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Exploring Quick Deployment Environment (QDE) & Offline / Internal Environments

Livestream
Speakers: Stephen Valdinger

This appliance allows you to have all the infrastructure required to use Chocolatey successfully in an organization, in 1 stream-lined appliance! We’ll go over what’s on the box, and how to set it up and get started.

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Choco CCM Module (Deployments / Integrations / Reporting)

Livestream
Speakers: Stephen Valdinger, Rain Sallow

PowerShell loves APIs, and so do we! So we wrote a PowerShell module to interact with the API behind Central Management. We’ll show off some of the cool things you can do with it in this session.

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Accelerate Automation of Windows with Ansible + Chocolatey

Webinar
Speakers: Adil Leghari, Paul Broadwith, George James

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. Separate Registration Required!

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Chocolatey Integrations Discussion (including SCCM & Intune)

Livestream
Speakers: Chocolatey Team

Are you using Configuration Management platforms like Puppet, SCCM, or Intune? Good news! Chocolatey can integrate with all these tools as well! Come find out how.

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Exploring Self-Service Anywhere

Livestream
Speakers: Paul Broadwith

Join Paul and discover how Chocolatey can empower your users to manage software on their computers, freeing up your IT team and other resources by harnessing the power of Chocolatey GUI and Chocolatey For Business.

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R&D Show and Tell

Livestream
Speakers: Rob Reynolds, Stephen Valdinger

Our R&D team and especially Stephen is always coming up with some really cool concepts, but not all of them make it into the product.

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Q&A Panel Session & Wrap

Livestream
Speakers: Chocolatey Team

We’ll take live questions from the Chocolatey Community here, to be submitted via the chat. If we have time, we’ll cover some common questions posed by Organizations we’ve helped.

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Holiday Holly

Event Speakers

Rob Reynolds
Rob Reynolds

Chocolatey Founder

Rob is a developer turned founder with 14+ years experience in infrastructure automation and modern automation approaches. He excels in taking hard concepts and making them approachable and easy.

Paul Broadwith
Paul Broadwith

Senior Technical Engineer at Chocolatey Software

Paul Broadwith of Glasgow Scotland has 25+ years in IT in financial, government, manufacturing and services sectors. He is the Lead Engineer on Boxstarter and cChoco DSC Resource.

Gary Ewan Park
Gary Ewan Park

Senior Software Engineer at Chocolatey Software

Gary Ewan Park has 10+ years working as a developer in the Oil and Gas Industry. He is the primary maintainer on the Chocolatey GUI project and the lead automation expert on Chocolatey Central Management.

Rain Sallow
Rain Sallow

Software Engineer at Chocolatey Software

Rain is a Chocolatey Software Engineer who spends most of their time working with PowerShell, C#, EntityFramework and ASP.NET Core. Keeping everything working as best we can, and improving things wherever possible.

Adil Leghari
Adil Leghari

Senior Solutions Engineer at Chocolatey Software

Adil Leghari is a 15-year Sysadmin who is super-passionate about PowerShell and automation. He is a co-founder of the Pacific Northwest PowerShell User Group and a co-host of BridgeConf. When not working at Chocolatey, he enjoys long walks on the beach, candlelit dinners, and designing stickers.

Stephen Valdinger
Stephen Valdinger

Solutions Engineer at Chocolatey Software

Stephen has been messing with technology professionally since 2007, after a childhood of tearing apart anything that plugged into a wall to the chagrin of his parents. He's focused on PowerShell and automation the last 5 years, and always looks for creative ways to solve complex problems.

Holiday Holly

Featuring Appearances From

Mukesh Sharma
Mukesh Sharma

Co-Founder & COO of Chocolatey

Mukesh is passionate about helping our customers on the Windows Automation journey. He has spent 20+ years helping various organizations adopt new disruptive technologies rapidly and consistently; from virtualization, cloud, data analytics to DevOps/WinOps. He is always seeking out opportunities to offer the customer a better experience than they expect.

George James
George James

Solutions Architect (Global Partner, Solutions Architecture) at Red Hat

George is a Solutions Architect for Red Hat (Global Partner, Solution Architecture). He has over 20 years experience in IT for a large financial services company. George Specializes in Network and Windows Automation with Ansible.