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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Downloads of v


Last Update:

17 Nov 2014

Package Maintainer(s):

Software Author(s):

  • RubyInstaller Contributors


Ruby DevKit admin

Ruby DevKit (1.8 & 1.9)

  • 1
  • 2
  • 3 | Updated: 17 Nov 2014



Downloads of v



Software Author(s):

  • RubyInstaller Contributors


Ruby DevKit admin

Ruby DevKit (1.8 & 1.9)

  • 1
  • 2
  • 3

Some Checks Have Failed or Are Not Yet Complete

Not All Tests Have Passed

Validation Testing Unknown

Verification Testing Failed


Scan Testing Successful:

No detections found in any package files

Learn More

Deployment Method: Individual Install, Upgrade, & Uninstall

To install Ruby DevKit (1.8 & 1.9), run the following command from the command line or from PowerShell:


To upgrade Ruby DevKit (1.8 & 1.9), run the following command from the command line or from PowerShell:


To uninstall Ruby DevKit (1.8 & 1.9), run the following command from the command line or from PowerShell:


Deployment Method:


This applies to both open source and commercial editions of Chocolatey.

1. Enter Your Internal Repository Url

(this should look similar to

2. Setup Your Environment

1. Ensure you are set for organizational deployment

Please see the organizational deployment guide

2. Get the package into your environment

  • Open Source or Commercial:
    • Proxy Repository - Create a proxy nuget repository on Nexus, Artifactory Pro, or a proxy Chocolatey repository on ProGet. Point your upstream to Packages cache on first access automatically. Make sure your choco clients are using your proxy repository as a source and NOT the default community repository. See source command for more information.
    • You can also just download the package and push it to a repository Download

3. Copy Your Script

choco upgrade ruby.devkit -y --source="'INTERNAL REPO URL'" [other options]

See options you can pass to upgrade.

See best practices for scripting.

Add this to a PowerShell script or use a Batch script with tools and in places where you are calling directly to Chocolatey. If you are integrating, keep in mind enhanced exit codes.

If you do use a PowerShell script, use the following to ensure bad exit codes are shown as failures:

choco upgrade ruby.devkit -y --source="'INTERNAL REPO URL'" 

Write-Verbose "Exit code was $exitCode"
$validExitCodes = @(0, 1605, 1614, 1641, 3010)
if ($validExitCodes -contains $exitCode) {
  Exit 0

Exit $exitCode

- name: Install ruby.devkit
    name: ruby.devkit
    version: ''
    state: present

See docs at

chocolatey_package 'ruby.devkit' do
  action    :install
  source   'INTERNAL REPO URL'
  version  ''

See docs at

cChocoPackageInstaller ruby.devkit
    Name     = "ruby.devkit"
    Version  = ""
    Source   = "INTERNAL REPO URL"

Requires cChoco DSC Resource. See docs at

package { 'ruby.devkit':
  ensure   => '',
  provider => 'chocolatey',
  source   => 'INTERNAL REPO URL',

Requires Puppet Chocolatey Provider module. See docs at

4. If applicable - Chocolatey configuration/installation

See infrastructure management matrix for Chocolatey configuration elements and examples.

Package Approved

This package was approved by moderator gep13 on 21 Nov 2014.


Ruby Development Kit (DevKit) is a toolkit that makes it easy to build and use native C/C++ extensions such as RDiscount and RedCloth for Ruby on Windows.

This no longer takes a dependency on Ruby. Please install that first.

try {
  $binRoot = Get-BinRoot
  if ($binRoot -eq $null) {
    $binRoot = "$env:systemdrive\"

  $devKitInstallDir = join-path $binRoot 'DevKit'

  write-host "Chocolatey is installing DevKit to $devKitInstallDir"
  write-host "Please wait..."
  Start-sleep 3

  if (![System.IO.Directory]::Exists($devKitInstallDir)) {[System.IO.Directory]::CreateDirectory($devKitInstallDir)}
  $tempDir = "$env:TEMP\chocolatey\ruby.devkit"
  if (![System.IO.Directory]::Exists($tempDir)) {[System.IO.Directory]::CreateDirectory($tempDir)}
  $file = Join-Path $tempDir "ruby.devkitInstall.exe"
  Get-ChocolateyWebFile 'ruby.devkit' "$file" ''

  if ($($env:Path).ToLower().Contains("ruby") -eq $false) {
    $env:Path = [Environment]::GetEnvironmentVariable('Path',[System.EnvironmentVariableTarget]::Machine);

  # Preparation
  #If you previously installed the legacy DevKit devkit-3.4.5r3-20091110.7z, its artifacts were extracted into each Ruby installation and need to be manually removed. Remove the gcc.bat, make.bat, and sh.bat stub batch files in <RUBY_INSTALL_DIR>\bin and the <RUBY_INSTALL_DIR>\devkit subdirectory for each Ruby installation using the legacy DevKit.
  $pathItems = $env:Path
  foreach($pathItem in $pathItems -split ";") {
    if ($pathItem -ilike "*ruby*bin") {
      Write-Host "Removing legacy install devkit items from $pathItem if they exist"
      if ([System.IO.File]::Exists("$($pathItem)\gcc.bat")) { Remove-Item "$($pathItem)\gcc.bat" -force}
      if ([System.IO.File]::Exists("$($pathItem)\make.bat")) { Remove-Item "$($pathItem)\make.bat" -force}
      if ([System.IO.File]::Exists("$($pathItem)\sh.bat")) { Remove-Item "$($pathItem)\sh.bat" -force}
      $oldDevKit = Join-Path (Split-Path -Parent $pathItem) 'devkit'
      if ([System.IO.Directory]::Exists("$oldDevKit")) {[System.IO.Directory]::Delete($oldDevKit,$true)}

  # clean out the recommended directories
  # 2. Delete all the <DEVKIT_INSTALL_DIR> subdirectories and files except for config.yml. If you’ve made any customizations to the MSYS shell you may also want to keep files in the etc and home subdirectories.
  if ([System.IO.File]::Exists("$($devKitInstallDir)\config.yml")) {
    Write-Host "Moving config.yml to a holding location prior to extraction"
    Copy-Item "$($devKitInstallDir)\config.yml" "$tempDir" -Force

  if ([System.IO.Directory]::Exists("$($devKitInstallDir)\etc")) {
    Write-Host "Moving etc dir to a holding location prior to extraction"
    if (![System.IO.Directory]::Exists("$($tempDir)\etc")) {[System.IO.Directory]::CreateDirectory("$($tempDir)\etc")}
    Copy-Item "$($devKitInstallDir)\etc\*" "$($tempDir)\etc" -Force -Recurse

  if ([System.IO.Directory]::Exists("$($devKitInstallDir)\home")) {
    Write-Host "Moving home dir to a holding location prior to extraction"
    if (![System.IO.Directory]::Exists("$($tempDir)\home")) {[System.IO.Directory]::CreateDirectory("$($tempDir)\home")}
    Copy-Item "$($devKitInstallDir)\home\*" "$($tempDir)\home" -Force -Recurse

  write-host "Cleaning out the contents of $devKitInstallDir"
  start-sleep 1
  Remove-Item "$($devKitInstallDir)\*" -recurse -force

  # 3. Extract the new SFX DevKit into the same <DEVKIT_INSTALL_DIR> that you just cleaned up.
  write-host "Extracting the contents of $file to $devKitInstallDir"
  start-sleep 3
  #& 7za x -o"$devKitInstallDir" -y "$file"
  Start-Process "7za" -ArgumentList "x -o`"$devKitInstallDir`" -y `"$file`"" -Wait

  if ([System.IO.File]::Exists("$($tempDir)\config.yml")) {
    Write-Host "Moving config.yml back after extraction"
    Copy-Item "$($tempDir)\config.yml" "$devKitInstallDir" -Force

  if ([System.IO.Directory]::Exists("$($tempDir)\etc")) {
    Write-Host "Moving etc dir back after extraction"
    Copy-Item "$($tempDir)\etc\*" "$($devKitInstallDir)\etc" -Force -Recurse

  if ([System.IO.Directory]::Exists("$($tempDir)\home")) {
    Write-Host "Moving home dir back after extraction"
    Copy-Item "$($tempDir)\home\*" "$($devKitInstallDir)\home" -Force -Recurse

  # 4. Review your config.yml file to ensure it contains the root directories of all the installed Rubies you want enhanced to use the DevKit.
  Write-Host "You may want to configure your config.yml after this installation and rerun 'cinst ruby.devkit' if the defaults do not meet your needs"
  Start-Sleep 5
  # 5. From a Command Prompt, cd into the <DEVKIT_INSTALL_DIR> directory and run ruby dk.rb install --force. This will cause all your installed Rubies listed in config.yml to use the updated SFX DevKit when building native gems and update the DevKit’s helper scripts (devkit.rb and operating_system.rb) with any new functionality. For safety, the original helper scripts are timestamp archived beside the new helper scripts. It’s always a good idea to review the two versions (and potentially make modifications) to ensure configuration specific to your system still works as expected.
  Write-Host "Initializing and installing DevKit into Ruby."
  cd $devKitInstallDir
  & ruby dk.rb init
  & ruby dk.rb install --force

  start-sleep 3

  Write-ChocolateySuccess 'ruby.devkit'
} catch {
  Write-ChocolateyFailure 'ruby.devkit' "$($_.Exception.Message)"

Log in or click on link to see number of positives.

In cases where actual malware is found, the packages are subject to removal. Software sometimes has false positives. Moderators do not necessarily validate the safety of the underlying software, only that a package retrieves software from the official distribution point and/or validate embedded software against official distribution point (where distribution rights allow redistribution).

Chocolatey Pro provides runtime protection from possible malware.

Add to Builder Version Downloads Last Updated Status
Ruby DevKit (1.8 & 1.9) 4451 Sunday, November 10, 2013 Approved
Ruby DevKit 2703 Friday, February 3, 2012 Unknown
Ruby DevKit 591 Monday, January 9, 2012 Unknown
Ruby DevKit 4.5.2 757 Tuesday, August 23, 2011 Unknown
Discussion for the Ruby DevKit (1.8 & 1.9) Package

Ground Rules:

  • This discussion is only about Ruby DevKit (1.8 & 1.9) and the Ruby DevKit (1.8 & 1.9) package. If you have feedback for Chocolatey, please contact the Google Group.
  • This discussion will carry over multiple versions. If you have a comment about a particular version, please note that in your comments.
  • The maintainers of this Chocolatey Package will be notified about new comments that are posted to this Disqus thread, however, it is NOT a guarantee that you will get a response. If you do not hear back from the maintainers after posting a message below, please follow up by using the link on the left side of this page or follow this link to contact maintainers. If you still hear nothing back, please follow the package triage process.
  • Tell us what you love about the package or Ruby DevKit (1.8 & 1.9), or tell us what needs improvement.
  • Share your experiences with the package, or extra configuration or gotchas that you've found.
  • If you use a url, the comment will be flagged for moderation until you've been whitelisted. Disqus moderated comments are approved on a weekly schedule if not sooner. It could take between 1-5 days for your comment to show up.
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