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Chocolatey
The package manager for Windows
Easily Manage Software on
Windows with Chocolatey
Rob Reynolds
@ferventcoder
Rob Reynolds
• Senior Software Engineer at Puppet
• Creator and Founder of Chocolatey
• Enjoys long walks on the beach and designing
solutions that make hard things easy
• Co-wrote infrastructure framework 

known as the Chuck Norris Framework
• Over 10 years experience in 

infrastructure automation
• Obsesses over user experience
Agenda
• The Story of Windows
Automation
• Windows Software
Ecosystem
• Chocolatey
• Announcements
Questions at the End
• Lots to cover
• Write your question(s) down
Everybody Stand Up
• Sit down if
• You’ve never used Chocolatey
• You started in Chocolatey with 0.9.9.x
• 0.9.8.3x
• 0.9.8.24
• 0.9.8.x
• Who is left?
Let’s talk about a story…
possibly your story
The Story of Modern
Automation for Windows
PuppetConf 2016: Easily Manage Software on Windows with Chocolatey – Rob Reynolds, Puppet
You probably use or have
used traditional tools
Traditional Tools
• Manual Configuration
• Golden Images
• Endpoint management tools
• SCCM / GPO
• Not necessarily bad, just are harder to fit into
modern automation
Modern Automation
• Feature-Rich
• Infrastructure as Code
• Source Control
• Testable Infrastructure
• Reporting
• Centralized Management
More Modern Automation Tools
• Puppet (Config Management)
• PowerShell DSC
• PowerShell
Power scale
So you settled on Puppet
Puppet + Other Tools
• Puppet - Harness PowerShell
• Puppet - Harness PowerShell DSC
• Puppet and SCCM (GPOs, WSUS server)
• Use the complements where they are
strong
So you modernized your
Windows automation
And it was great. Rainbows
and Unicorns
PuppetConf 2016: Easily Manage Software on Windows with Chocolatey – Rob Reynolds, Puppet
PuppetConf 2016: Easily Manage Software on Windows with Chocolatey – Rob Reynolds, Puppet
PuppetConf 2016: Easily Manage Software on Windows with Chocolatey – Rob Reynolds, Puppet
Something wasn’t quite right…
Automating Windows
software installation was
still hard…
Software management may
account for 50-90% of your
automation
Traditionally Windows was
designed with Visual
Interfaces (GUIs) in mind.
There is no place more evident of
that still than with the Windows
Software Installer ecosystem
PuppetConf 2016: Easily Manage Software on Windows with Chocolatey – Rob Reynolds, Puppet
Windows Software Ecosystem
• Over 20 installer formats and
thousands of installers in the
wild
• Zips and other archive
formats
• Software installers are messy
• It’s like the Wild West
“There has to be a better
way”
So you went looking for a
solution
And you heard of this sweet
tool that manages software.
PuppetConf 2016: Easily Manage Software on Windows with Chocolatey – Rob Reynolds, Puppet
PuppetConf 2016: Easily Manage Software on Windows with Chocolatey – Rob Reynolds, Puppet
Chocolatey - Sane Software Management
• Easily manage the software lifecycle
• Native installers, zips, binaries
• PowerShell module simplifies work
• Packages are independent building
blocks
• Integrates with configuration
management
• Business friendly features
Chocolatey - The Approach
• Single, unifying interface - control
the chaos
• Decentralized - multiple places to
get packages, including internal
• PowerShell
• Flexible
• Secure
• Reliable
5+ years - proven technology
Community Package Repository
• https://chocolatey.org/
packages
• Community Feed / Community
Maintained
• Moderated as of October 2014
• Everything goes through
VirusTotal
• Organizations Should Not
Depend b/c Trust and Control
Hosting Your Own Package Server
• https://chocolatey.org/docs/how-to-host-feed
• Non-Windows Hosting
• Artifactory
• Sonatype Nexus
• NuGet Gallery proper
• ProGet / MyGet
• NuGet.Server / Chocolatey.Server
• Puppet - chocolatey/chocolatey_server module
Chocolatey Packages
• Zip files + Versioning, Dependencies & PowerShell
• Metadata - Software Information / Package Information
• PowerShell - https://chocolatey.org/docs/helpers-reference
• 30+ Built-in functions - turn hard tasks into 1 liners
• Handle additional missing installer logic (like add to PATH)
• Add options missing from installer arguments
• Files - drop in binaries, native installers
Creating Packages
• https://chocolatey.org/docs/create-
packages
• choco new
• Generates package files with most of
the work done
• Create your own packaging templates!
But wait, you have
Chocolatey for Business
Package Builder
Package Builder
• Package Builder automatically creates high quality packaging
from an installer/zip in 5-10 seconds
• Determines everything necessary for silently installing
software
• Supports passing urls (and checksums) - downloads files first
• Allows customization
• Supports exe, msi, 7z, zip, msu, and msp files
How does it work?
PuppetConf 2016: Easily Manage Software on Windows with Chocolatey – Rob Reynolds, Puppet
Package Internalizer
Package Internalizer
• Take advantage of existing packages without dependency on
the internet
• Downloads existing package and all remote resources
• Recompiles package to use those internal resources
• Option to download and point to other locations
• Ability to host packages on private internal repositories
Package Synchronizer
You detect a theme for
feature names
Package Synchronizer
• Chocolatey maintains state based on packages. System state
can be manipulated outside of Chocolatey
• Any Chocolatey command will trigger synchronization in
Chocolatey for Business
• Package Synchronizer syncs with manual software removal
• Syncs w/software that automatically upgrades, such as
Chrome
How does it work?
PuppetConf 2016: Easily Manage Software on Windows with Chocolatey – Rob Reynolds, Puppet
Other Enhancements
Other Enhancements
• https://chocolatey.org/docs/release-notes-licensed
• Auto-uninstaller more effective thanks to more
checks and Package Synchronizer
• Install/upgrade passing secrets
• Uninstall non-Chocolatey managed software
• Similar to built-in provider but ‘Git *’
+
puppetlabs/chocolatey
• https://puppet.com/blog/puppet-supported-module-chocolatey
• Everything from chocolatey/chocolatey - drop in replacement
• package resource
• ensure Chocolatey install
• Full configuration for Chocolatey
• chocolateysource
• chocolateyconfig
• chocolateyfeature
Chocolatey Provider is Supported!
Install Chocolatey
• Install and initial configuration
• Point to internal resources
Package Resource
• installable, uninstallable, upgradeable, versionable, holdable, install_options,
uninstall_options
• Still later: virtual_packages
Chocolatey Package Resource
• Built in provider requires
manifest maintenance
• Package resource default to
provider => chocolatey for
Windows.
• Platform agnostic packaging
chocolateysource
• Disable/remove default community repository
• Add your own sources
• user/password 

protected as well
• puppet resource

chocolateysource
chocolateyconfig
• Set config settings
• Full list available by

choco config list or

puppet resource chocolateyconfig
chocolateyfeature
• Enable/disable features
• Full list available by

choco feature list or

puppet resource chocolateyfeature
Demo
Announcements
Roadmap
• WSA support / Windows Nano Support
• More Security / More UX
• Package enhancements
• Package signing / security enhancements
• Extend Nuspec further - name, version, release,
architecture
Package Builder
<intentionally left blank>
b/c Demo
Package Builder vNext
• choco new —from-programs-and-features
• Currently supports MSI
• Support for other types 

will come later
• Package Builder visual 

interface
• Transition from existing 

tools/processes
Package Internalizer
Package Internalizer
• Also a visual interface
• Provides a better transition towards command line
interfaces
Package Synchronizer
Package Synchronizer v2
• Bring software not managed with Chocolatey into managed
packages
• choco sync
• Find existing packages
• Optionally generate packages for sync
Package Modernizer
Package Modernizer
• You have existing packages
• Bring them up to best practices
• Modernizer will upgrade packaging files in place
• choco modernize
Self-Service Install (Non-
Administrators)
Self-Service Installer
• 1st feature not named Package *
• Non-admins can choose what to install
• Runs as an administrative background service
• Also choco upgrade all on your schedule
Questions
+
• Rob
• @ferventcoder
• ferventcoder at
gmail
Evaluate Chocolatey for Business in your environment - special discount until December 31, 2016 for Puppet Enterprise customers
(mention PuppetConf2016) - https://chocolatey.org/compare
Ad

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