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Chocolatey
The package manager for Windows
Chocolatey for Organizations:
Easily Manage Software
Rob Reynolds
Founder
Chocolatey Software
@ferventcoder
Rob Reynolds
• 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 13 years experience in 

infrastructure automation
• Obsesses over user experience
• Microsoft MVP for both Cloud and Datacenter
Management and Visual Studio and
Development Technologies
Agenda
• Chocolatey
• Organizational
Use
• Demos
Kicking Off
• We are going to cover a
lot of ground quickly
• You will see open source
& commercial features
• https://chocolatey.org/
compare#compare
What is Chocolatey?
Chocolatey is…
• Software management / package
management
• Universal management for zips,
scripts, binaries, and installers
• Software deployment
automation packages
With Chocolatey you can…
• Manage ANY software, not just installers
• Define dependencies
• Write a software deployment one time (with PowerShell!)
• Test your deployments - gain confidence long before a prod deployment
• Deploy to any supported version of Windows (including Server.Core /
Docker containers)
• On prem, in the cloud, etc
• With any remote deployment tool (Puppet, Chef, Ansible, DSC, SCCM,
LanDesk, MDT, etc) or combination
• Track and Report on software
Chocolatey allows you to
deploy any Windows software,
anywhere,
with anything,
and manage and track that software over time.
Did we mention PowerShell?
So that sounds amazing.
Here’s a dose of reality
There is nothing you can
purchase or implement that
removes all work
Chocolatey is a Framework
• There is still work, it is not magic. There is no tool that
does it all - sorry to burst your bubble
• It is amazingly flexible
• It does make software management very easy
• There are steps into automation you can do to really
reduce your work - Chocolatey is a catalyst for that
• It is lightweight
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Editions
• Open Source - DIY, Apache v2
license
• C4B (Chocolatey for Business) -
More UIs, smoother experience,
more precision, and features
geared towards organizational use
• Easy to migrate between the two
Commercial Capabilities
Real-time Insights
Chocolatey Central Management
Enhance User Experience
Self-Service GUI
Improve Accuracy & Simplify Software
Management
Package Synchronizer
Improve Security & Controls
Package Internalizer & Package Audit
Accelerate Deployments
Package Builder & Package Uploader
Optimization & Environments
Package Reducer & Package Throttle
So What is Chocolatey?
It is software management
that works
Why Chocolatey? Because
the following Is NOT how we
should manage software
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Organizational Use
What’s possible?
• This is a framework Yelp
shared with us at
Chocolatey Fest 2018
• https://
www.youtube.com/
watch?v=wSgWVklw4xA
Organizational Use
Internal Repositories
Artifactory, Nexus, ProGet
Continuous Integration
Jenkins, Team City, etc
Reporting
Current, Central
Management, DIY
Deployment &
Management
Puppet, Chef, SCCM, etc
Source Control
Git & Git LFS
Packaging
choco new, Package
Builder, internalization
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Repositories
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Why Can’t I Just Use The
Community Repository?
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Community Package Repository
• https://chocolatey.org/packages
• Community Feed / Community
Maintained
• Moderated as of October 2014
• Everything goes through VirusTotal
• Organizations Should Avoid
• Not Fully Reliable - public repo
means subject to distribution
rights (download CDN cache
feature helps)
• Trust and Control
Internal Repositories
• https://chocolatey.org/docs/how-to-host-feed
• Artifactory Pro (cross-platform)
• Sonatype Nexus (cross-platform)
• Inedo’s ProGet
• MyGet (hosted)
• Chocolatey.Server
• NuGet.Server / NuGet Gallery proper
• Visual Studio Team Services (v2 endpoints) / TFS
• File Share (DFS, CIFS, SMB) / SCCM Distribution points
Commercial options:
• Web Interface
• One Install / Multiple
repositories
• Multiple repository
types, not just
NuGet/Chocolatey
Packaging
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Package Internalizer - “Convert existing packages
to 100% offline and reliable”
• 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
• Visual Interface coming
Creating Packages
• https://chocolatey.org/docs/create-
packages
• choco new
• Generates package files with most of
the work done
• Create your own packaging templates!
Package Builder- “Generate software deployment
packages in seconds”
• Package Builder automatically creates
high quality packaging from an installer/
zip in 5-10 seconds
• Determines everything necessary for
silently installing software for 70% of
installers out there
• Supports passing urls (and checksums) -
downloads files first
• Allows customization
• Supports exe, msi, 7z, zip, msu, and msp
files
Non-Silent Installers?
• MSI Repackaging
• C4B Customers can use
optional Packaging
Services for small fee
Deployment &
Management
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Infrastructure Management
• https://chocolatey.org/docs/features-infrastructure-automation
• Tight - provider-based
• Chef (built-in), cookbook
• Puppet
• PowerShell DSC
• Ansible
• Saltstack
• Script-based
• Octopus Deploy
• Boxstarter
• SCCM
• RMM, or really anything that can run scripts
Reporting
Inventory - Comprehensive Software Audit
• Exclusive to Chocolatey - Visibility
beyond just the software ‘installed’ in
Programs & Features
• Track versions of zip archives & own
internal software that is not visible in
system installation.
• Get a complete view of your systems.
Chocolatey reports applications in
systems not directly under its
management.
• Package Audit adds who, when, and
history
Compliance – Audit Out of Date Software
• choco outdated
• Comprehensive reporting
on available upgrades
• See what will upgrade on
next maintenance
window
• Pinned items won't
upgrade until pin is
remove
Package Synchronizer - Auto Sync
• Chocolatey maintains state based
on packages. System state can be
manipulated outside of Chocolatey
• Any Chocolatey command will
trigger synchronization in licensed
editions of Chocolatey
• Package Synchronizer syncs with
manual software removal
• Syncs w/software that
automatically upgrades, such as
Chrome
Package Synchronizer - All Packages in
Programs and Features
• Programs and Features
represents only 50-80% of
the software on a machine
• Chocolatey brings managed
entries for non-installer
packages
• Supporting legacy inventory
reporting systems is now a
snap
• Do not need to build MSIs /
Installers for internal use
just to support legacy
reporting
Chocolatey Central Management
• See reports /
information across the
org
• Modules / plugins
coming
• Deployments
Other Features
• https://chocolatey.org/docs/release-notes
• Internal sources (like ProGet)
• choco upgrade all - Windows update for
your 3rd party and internal software
• Shimming - like symlinks but better
• Pass install arguments directly through to
installer (append or override package args)
• Package Parameters to adjust logic in
packages
• Handles locking on upgrades in package
folders
• Great reference docs - https://
chocolatey.org/docs/commands-
reference & https://chocolatey.org/
docs/helpers-reference
• Excellent open source support
community
• 30+ built-in PowerShell Functions
• Extend functionality with your own
PowerShell Modules
• Custom Package Templates
• Can manage anything on Windows
Other Features (C4B)
• https://chocolatey.org/docs/
release-notes-licensed
• Auto-uninstaller more effective -
uninstaller detection / Package
Synchronizer
• Install/upgrade keeping secrets
out of logs
• Ubiquitous Install Directory
Option
• More built-in PowerShell functions
• Uninstall non-Chocolatey managed
software
• Direct Installer - install directly from
exe/msi
• Package Throttle
• Runtime malware protection
• CDN Cache
• Professional Packaging Services
• Amazing expert support team -
https://chocolatey.org/support
Chocolatey Roadmap
• https://chocolatey.org/
docs/roadmap
• Choco Deploy CLI (C4B)
• WSA / AppX / MSIx
• Package Enhancements
• Pack Validation
• More GUIs (C4B)
• Authenticode / GPG 

Signing
• Package Grid (C4B)
• Deferred Installer (C4B)
• Others (just ask)
Learn More
• https://chocolatey.org/
contact (choose “Sales”)
• https://chocolatey.org/
docs
• Expansive community
• chocolateynuget on
twitter
Anyone here doing all of
this?
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019
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Chocolatey for Organizations: Easily Manage Software - PowerShell Summit 2019

  • 1. Chocolatey The package manager for Windows Chocolatey for Organizations: Easily Manage Software Rob Reynolds Founder Chocolatey Software @ferventcoder
  • 2. Rob Reynolds • 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 13 years experience in 
 infrastructure automation • Obsesses over user experience • Microsoft MVP for both Cloud and Datacenter Management and Visual Studio and Development Technologies
  • 4. Kicking Off • We are going to cover a lot of ground quickly • You will see open source & commercial features • https://chocolatey.org/ compare#compare
  • 6. Chocolatey is… • Software management / package management • Universal management for zips, scripts, binaries, and installers • Software deployment automation packages
  • 7. With Chocolatey you can… • Manage ANY software, not just installers • Define dependencies • Write a software deployment one time (with PowerShell!) • Test your deployments - gain confidence long before a prod deployment • Deploy to any supported version of Windows (including Server.Core / Docker containers) • On prem, in the cloud, etc • With any remote deployment tool (Puppet, Chef, Ansible, DSC, SCCM, LanDesk, MDT, etc) or combination • Track and Report on software
  • 8. Chocolatey allows you to deploy any Windows software, anywhere, with anything, and manage and track that software over time. Did we mention PowerShell?
  • 9. So that sounds amazing. Here’s a dose of reality
  • 10. There is nothing you can purchase or implement that removes all work
  • 11. Chocolatey is a Framework • There is still work, it is not magic. There is no tool that does it all - sorry to burst your bubble • It is amazingly flexible • It does make software management very easy • There are steps into automation you can do to really reduce your work - Chocolatey is a catalyst for that • It is lightweight
  • 14. Editions • Open Source - DIY, Apache v2 license • C4B (Chocolatey for Business) - More UIs, smoother experience, more precision, and features geared towards organizational use • Easy to migrate between the two
  • 15. Commercial Capabilities Real-time Insights Chocolatey Central Management Enhance User Experience Self-Service GUI Improve Accuracy & Simplify Software Management Package Synchronizer Improve Security & Controls Package Internalizer & Package Audit Accelerate Deployments Package Builder & Package Uploader Optimization & Environments Package Reducer & Package Throttle
  • 16. So What is Chocolatey? It is software management that works
  • 17. Why Chocolatey? Because the following Is NOT how we should manage software
  • 21. What’s possible? • This is a framework Yelp shared with us at Chocolatey Fest 2018 • https:// www.youtube.com/ watch?v=wSgWVklw4xA
  • 22. Organizational Use Internal Repositories Artifactory, Nexus, ProGet Continuous Integration Jenkins, Team City, etc Reporting Current, Central Management, DIY Deployment & Management Puppet, Chef, SCCM, etc Source Control Git & Git LFS Packaging choco new, Package Builder, internalization
  • 26. Why Can’t I Just Use The Community Repository?
  • 28. Community Package Repository • https://chocolatey.org/packages • Community Feed / Community Maintained • Moderated as of October 2014 • Everything goes through VirusTotal • Organizations Should Avoid • Not Fully Reliable - public repo means subject to distribution rights (download CDN cache feature helps) • Trust and Control
  • 29. Internal Repositories • https://chocolatey.org/docs/how-to-host-feed • Artifactory Pro (cross-platform) • Sonatype Nexus (cross-platform) • Inedo’s ProGet • MyGet (hosted) • Chocolatey.Server • NuGet.Server / NuGet Gallery proper • Visual Studio Team Services (v2 endpoints) / TFS • File Share (DFS, CIFS, SMB) / SCCM Distribution points Commercial options: • Web Interface • One Install / Multiple repositories • Multiple repository types, not just NuGet/Chocolatey
  • 32. Package Internalizer - “Convert existing packages to 100% offline and reliable” • 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 • Visual Interface coming
  • 33. Creating Packages • https://chocolatey.org/docs/create- packages • choco new • Generates package files with most of the work done • Create your own packaging templates!
  • 34. Package Builder- “Generate software deployment packages in seconds” • Package Builder automatically creates high quality packaging from an installer/ zip in 5-10 seconds • Determines everything necessary for silently installing software for 70% of installers out there • Supports passing urls (and checksums) - downloads files first • Allows customization • Supports exe, msi, 7z, zip, msu, and msp files
  • 35. Non-Silent Installers? • MSI Repackaging • C4B Customers can use optional Packaging Services for small fee
  • 38. Infrastructure Management • https://chocolatey.org/docs/features-infrastructure-automation • Tight - provider-based • Chef (built-in), cookbook • Puppet • PowerShell DSC • Ansible • Saltstack • Script-based • Octopus Deploy • Boxstarter • SCCM • RMM, or really anything that can run scripts
  • 40. Inventory - Comprehensive Software Audit • Exclusive to Chocolatey - Visibility beyond just the software ‘installed’ in Programs & Features • Track versions of zip archives & own internal software that is not visible in system installation. • Get a complete view of your systems. Chocolatey reports applications in systems not directly under its management. • Package Audit adds who, when, and history
  • 41. Compliance – Audit Out of Date Software • choco outdated • Comprehensive reporting on available upgrades • See what will upgrade on next maintenance window • Pinned items won't upgrade until pin is remove
  • 42. Package Synchronizer - Auto Sync • Chocolatey maintains state based on packages. System state can be manipulated outside of Chocolatey • Any Chocolatey command will trigger synchronization in licensed editions of Chocolatey • Package Synchronizer syncs with manual software removal • Syncs w/software that automatically upgrades, such as Chrome
  • 43. Package Synchronizer - All Packages in Programs and Features • Programs and Features represents only 50-80% of the software on a machine • Chocolatey brings managed entries for non-installer packages • Supporting legacy inventory reporting systems is now a snap • Do not need to build MSIs / Installers for internal use just to support legacy reporting
  • 44. Chocolatey Central Management • See reports / information across the org • Modules / plugins coming • Deployments
  • 45. Other Features • https://chocolatey.org/docs/release-notes • Internal sources (like ProGet) • choco upgrade all - Windows update for your 3rd party and internal software • Shimming - like symlinks but better • Pass install arguments directly through to installer (append or override package args) • Package Parameters to adjust logic in packages • Handles locking on upgrades in package folders • Great reference docs - https:// chocolatey.org/docs/commands- reference & https://chocolatey.org/ docs/helpers-reference • Excellent open source support community • 30+ built-in PowerShell Functions • Extend functionality with your own PowerShell Modules • Custom Package Templates • Can manage anything on Windows
  • 46. Other Features (C4B) • https://chocolatey.org/docs/ release-notes-licensed • Auto-uninstaller more effective - uninstaller detection / Package Synchronizer • Install/upgrade keeping secrets out of logs • Ubiquitous Install Directory Option • More built-in PowerShell functions • Uninstall non-Chocolatey managed software • Direct Installer - install directly from exe/msi • Package Throttle • Runtime malware protection • CDN Cache • Professional Packaging Services • Amazing expert support team - https://chocolatey.org/support
  • 47. Chocolatey Roadmap • https://chocolatey.org/ docs/roadmap • Choco Deploy CLI (C4B) • WSA / AppX / MSIx • Package Enhancements • Pack Validation • More GUIs (C4B) • Authenticode / GPG 
 Signing • Package Grid (C4B) • Deferred Installer (C4B) • Others (just ask)
  • 48. Learn More • https://chocolatey.org/ contact (choose “Sales”) • https://chocolatey.org/ docs • Expansive community • chocolateynuget on twitter
  • 49. Anyone here doing all of this?
  • 52. Demos