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Chocolatey
The package manager for Windows
Modern Software Management w/
Chocolatey
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 10 years experience in 

infrastructure automation
• Obsesses over user experience
• Microsoft MVP for whatever they are
calling .NET area now
Agenda
• Chocolatey
• Why
• What
• Features
• Demo
• Questions
Why Chocolatey?
Software management may
account for 50-90% of your
automation
Windows Software Ecosystem
• Over 20 installer formats and
thousands of installers in the
wild
• Zips and other archive formats
• Software installers are messy
• Deploy internal/3rd party
software using same approach?
• It’s like the Wild West
Why?
• You already deploy
software
• Likely already use
deployment scripts
• Delivery mechanisms
• Internal Software
Why?
Why?
But Seriously, Why Chocolatey?
• Reporting
• Features
• Offline
• Secure
• Flexibility
• Beyond Programs and Features
• Beyond just running installers
• Integrates with everything
But Seriously, Why Chocolatey?
• Focused solution - does 1 thing very well for over 6+ years
• Uses PowerShell - not learning new or proprietary
technologies
• One approach for all software management - 3rd party
and internal
• Reinventing Chocolatey could cost over $1 million
• Hundreds of other companies are using it, there must be a
reason
What is Chocolatey?
What is Chocolatey?
• Software Management
• PowerShell
• Fancy zip files = “packages”
• Packages are independent software deployment
artifacts
• Takes your deployment scripts to the next level
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 and RMM tools
• Business friendly features
Chocolatey - The Approach
• Single, unifying interface - control
the chaos
• Decentralized - multiple places to
get packages, including internal
• PowerShell
• Flexible
• Secure
• Reliable
6+ years - proven technology
Organizational / Internal
Use
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
Sweet Features
FOSS vs Chocolatey for Business (C4B)
• Chocolatey open source (FOSS) == package
management
• Works well in organizational use
• C4B == complete software management
• Smoother experience
• Builds on top of FOSS
• Better system integration, endpoint
management, etc
• Better visual interfaces (GUIs)
• Features geared specifically towards
organizational use
Smart Installs / Smarter Upgrades
• Track software installation in Programs &
Features to map packages to system
installs
• Track environment variable changes
• Leave out guesswork by reporting on
software installation location
• Upgrades - Use Xml Document Transform
(XDT) for .NET configuration file changes
• Exclusive to Chocolatey - Use new tools /
commands without closing / re-opening
your shell for environment changes to
take effect
Graphical Interface - Chocolatey GUI
• Configure Chocolatey
• Manage software
installations
Automatic Uninstallation
• Exclusive to Chocolatey -
Automatically uninstall
over 90% of installations
without uninstall script
• AutoUninstaller reduces
time by not developing
and managing uninstall
scripts
Integrates with Everything
• https://chocolatey.org/docs/features-infrastructure-
automation
• Puppet
• Chef (built-in), cookbook
• PowerShell DSC
• Ansible
• Saltstack
• Octopus Deploy
• Boxstarter
• SCCM
• RMM, or really anything that can run scripts
Reporting / Auditing
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 (C4B) adds who and
when
Logging - Detailed Reporting
• Log file captures very
detailed information -
environment and state
• Reduces rollback /
recreation necessity
Compliance – Audit Out of Date Software
• choco outdated
• Comprehensive reporting on available upgrades
• See what will upgrade on next maintenance window
Package Repository
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
• Visual Studio Team Services
Creating Software
Deployment “Packages”
Chocolatey Packages
• Terminology: "Package" is nupkg file, "Software" is binaries or installers
• Zip files + Versioning, Dependencies & PowerShell
• Metadata - Software Information / Package Information
• PowerShell - https://chocolatey.org/docs/helpers-reference
• 30+ Built-in functions - complex tasks become 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!
Package Builder (C4B) - “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
• Supports passing urls (and
checksums) - downloads files first
• Allows customization
• Supports exe, msi, 7z, zip, msu, and
msp files
Package Internalizer (C4B) - “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
How does it work?
Package Synchronizer (C4B)
- stay in sync w/system
Package Synchronizer (Licensed) - 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 (C4B) - 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
Package Synchronizer (C4B) - Choco Sync
Command
• Brings all software in
Programs and Features
under Chocolatey
management
• Generates packaging and
baselines to Chocolatey
install
• Provides packaging code to
take back to source control
Self-Service (C4B) - “Non-
administrative desktop users
can install/upgrade software!”
Self-Service Installer / Background Mode (C4B)
Package Reducer (Licensed)
• Reduce Chocolatey space
usage down automatically
• Reduction on install/
upgrade
• choco optimize to clean
existing
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
• Central Management UI (C4B)
• Choco Deploy CLI (C4B)
• WSA / Windows Nano Support
• PowerShell
PackageManagement Official
Provider
• Package Enhancements
• Pack Validation
• Virtual packages
• GPG Signing
• Package Grid (C4B)
• Deferred Installer (C4B)
• Possible support on other
platforms
Demo
This is you
This is you on Chocolatey
Any Questions?
https://
chocolatey.org/
contact
• ferventcoder -
twitter, gmail, etc
Questions?

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Modern Software Management on Windows w/Chocolatey

  • 1. Chocolatey The package manager for Windows Modern Software Management w/ Chocolatey 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 10 years experience in 
 infrastructure automation • Obsesses over user experience • Microsoft MVP for whatever they are calling .NET area now
  • 3. Agenda • Chocolatey • Why • What • Features • Demo • Questions
  • 4.
  • 5.
  • 7. Software management may account for 50-90% of your automation
  • 8. Windows Software Ecosystem • Over 20 installer formats and thousands of installers in the wild • Zips and other archive formats • Software installers are messy • Deploy internal/3rd party software using same approach? • It’s like the Wild West
  • 9. Why? • You already deploy software • Likely already use deployment scripts • Delivery mechanisms • Internal Software
  • 10. Why?
  • 11. Why?
  • 12.
  • 13. But Seriously, Why Chocolatey? • Reporting • Features • Offline • Secure • Flexibility • Beyond Programs and Features • Beyond just running installers • Integrates with everything
  • 14. But Seriously, Why Chocolatey? • Focused solution - does 1 thing very well for over 6+ years • Uses PowerShell - not learning new or proprietary technologies • One approach for all software management - 3rd party and internal • Reinventing Chocolatey could cost over $1 million • Hundreds of other companies are using it, there must be a reason
  • 16. What is Chocolatey? • Software Management • PowerShell • Fancy zip files = “packages” • Packages are independent software deployment artifacts • Takes your deployment scripts to the next level
  • 17. 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 and RMM tools • Business friendly features
  • 18. Chocolatey - The Approach • Single, unifying interface - control the chaos • Decentralized - multiple places to get packages, including internal • PowerShell • Flexible • Secure • Reliable 6+ years - proven technology
  • 20.
  • 21. 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
  • 23. FOSS vs Chocolatey for Business (C4B) • Chocolatey open source (FOSS) == package management • Works well in organizational use • C4B == complete software management • Smoother experience • Builds on top of FOSS • Better system integration, endpoint management, etc • Better visual interfaces (GUIs) • Features geared specifically towards organizational use
  • 24. Smart Installs / Smarter Upgrades • Track software installation in Programs & Features to map packages to system installs • Track environment variable changes • Leave out guesswork by reporting on software installation location • Upgrades - Use Xml Document Transform (XDT) for .NET configuration file changes • Exclusive to Chocolatey - Use new tools / commands without closing / re-opening your shell for environment changes to take effect
  • 25. Graphical Interface - Chocolatey GUI • Configure Chocolatey • Manage software installations
  • 26. Automatic Uninstallation • Exclusive to Chocolatey - Automatically uninstall over 90% of installations without uninstall script • AutoUninstaller reduces time by not developing and managing uninstall scripts
  • 27. Integrates with Everything • https://chocolatey.org/docs/features-infrastructure- automation • Puppet • Chef (built-in), cookbook • PowerShell DSC • Ansible • Saltstack • Octopus Deploy • Boxstarter • SCCM • RMM, or really anything that can run scripts
  • 29. 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 (C4B) adds who and when
  • 30. Logging - Detailed Reporting • Log file captures very detailed information - environment and state • Reduces rollback / recreation necessity
  • 31. Compliance – Audit Out of Date Software • choco outdated • Comprehensive reporting on available upgrades • See what will upgrade on next maintenance window
  • 33. 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 • Visual Studio Team Services
  • 35. Chocolatey Packages • Terminology: "Package" is nupkg file, "Software" is binaries or installers • Zip files + Versioning, Dependencies & PowerShell • Metadata - Software Information / Package Information • PowerShell - https://chocolatey.org/docs/helpers-reference • 30+ Built-in functions - complex tasks become 1 liners • Handle additional missing installer logic (like add to PATH) • Add options missing from installer arguments • Files - drop in binaries, native installers
  • 36. Creating Packages • https://chocolatey.org/docs/create- packages • choco new • Generates package files with most of the work done • Create your own packaging templates!
  • 37.
  • 38. Package Builder (C4B) - “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 • Supports passing urls (and checksums) - downloads files first • Allows customization • Supports exe, msi, 7z, zip, msu, and msp files
  • 39. Package Internalizer (C4B) - “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
  • 40. How does it work?
  • 41.
  • 42. Package Synchronizer (C4B) - stay in sync w/system
  • 43. Package Synchronizer (Licensed) - 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
  • 44. Package Synchronizer (C4B) - 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
  • 45. Package Synchronizer (C4B) - Choco Sync Command • Brings all software in Programs and Features under Chocolatey management • Generates packaging and baselines to Chocolatey install • Provides packaging code to take back to source control
  • 46. Self-Service (C4B) - “Non- administrative desktop users can install/upgrade software!”
  • 47. Self-Service Installer / Background Mode (C4B)
  • 48. Package Reducer (Licensed) • Reduce Chocolatey space usage down automatically • Reduction on install/ upgrade • choco optimize to clean existing
  • 49. 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
  • 50. 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
  • 51. Chocolatey Roadmap • https://chocolatey.org/docs/ roadmap • Central Management UI (C4B) • Choco Deploy CLI (C4B) • WSA / Windows Nano Support • PowerShell PackageManagement Official Provider • Package Enhancements • Pack Validation • Virtual packages • GPG Signing • Package Grid (C4B) • Deferred Installer (C4B) • Possible support on other platforms
  • 52. Demo
  • 54.
  • 55. This is you on Chocolatey
  • 56.