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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Installing Chocolatey

Step 1: Subscribe to the Chocolatey Newsletter (Optional)

Be the first to know about upcoming features, security releases, and news about Chocolatey.

Step 2: Choose Your Installation Method

Know the Requirements:

1. Choose How to Install Chocolatey:

Install Chocolatey for Individual Use:

  1. First, ensure that you are using an administrative shell - you can also install as a non-admin, check out Non-Administrative Installation.
  2. Install with powershell.exe


    Please inspect https://community.chocolatey.org/install.ps1 prior to running any of these scripts to ensure safety. We already know it's safe, but you should verify the security and contents of any script from the internet you are not familiar with. All of these scripts download a remote PowerShell script and execute it on your machine. We take security very seriously. Learn more about our security protocols.

    With PowerShell, you must ensure Get-ExecutionPolicy is not Restricted. We suggest using Bypass to bypass the policy to get things installed or AllSigned for quite a bit more security.

    • Run Get-ExecutionPolicy. If it returns Restricted, then run Set-ExecutionPolicy AllSigned or Set-ExecutionPolicy Bypass -Scope Process.

    Now run the following command:

  3. Paste the copied text into your shell and press Enter.
  4. Wait a few seconds for the command to complete.
  5. If you don't see any errors, you are ready to use Chocolatey! Type choco or choco -? now, or see Getting Started for usage instructions.

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

2. Enter Your Internal Repository Url

(this should look similar to https://community.chocolatey.org/api/v2/)

3. Setup Your Environment

  1. Ensure you are set for organizational deployment
  2. Download the Chocolatey package
  3. Put the Chocolatey package on your internal repository

4. Get Your Scripts

Save the following as ChocolateyInstall.ps1:

# Download and install Chocolatey nupkg from an OData (HTTP/HTTPS) url such as Artifactory, Nexus, ProGet (all of these are recommended for organizational use), or Chocolatey.Server (great for smaller organizations and POCs)
# This is where you see the top level API - with xml to Packages - should look nearly the same as https://community.chocolatey.org/api/v2/
# If you are using Nexus, always add the trailing slash or it won't work
# === EDIT HERE ===
$packageRepo = 'INTERNAL REPO URL'

# If the above $packageRepo repository requires authentication, add the username and password here. Otherwise these leave these as empty strings.
$repoUsername = ''    # this must be empty is NOT using authentication
$repoPassword = ''    # this must be empty if NOT using authentication

# Determine unzipping method
# 7zip is the most compatible, but you need an internally hosted 7za.exe.
# Make sure the version matches for the arguments as well.
# Built-in does not work with Server Core, but if you have PowerShell 5
# it uses Expand-Archive instead of COM
$unzipMethod = 'builtin'
#$unzipMethod = '7zip'
#$7zipUrl = 'https://chocolatey.org/7za.exe' (download this file, host internally, and update this to internal)

# Prior to running this script, in a PowerShell session, you can set the
# following environment variables and it will affect the output

# - $env:ChocolateyEnvironmentDebug = 'true' # see output
# - $env:chocolateyIgnoreProxy = 'true' # ignore proxy
# - $env:chocolateyProxyLocation = '' # explicit proxy
# - $env:chocolateyProxyUser = '' # explicit proxy user name (optional)
# - $env:chocolateyProxyPassword = '' # explicit proxy password (optional)

# Ensure we can run everything
Set-ExecutionPolicy Bypass -Scope Process -Force;

# If the repository requires authentication, create the Credential object
if ((-not [string]::IsNullOrEmpty($repoUsername)) -and (-not [string]::IsNullOrEmpty($repoPassword))) {
$securePassword = ConvertTo-SecureString $repoPassword -AsPlainText -Force
$repoCreds = New-Object System.Management.Automation.PSCredential ($repoUsername, $securePassword)

$searchUrl = ($packageRepo.Trim('/'), 'Packages()?$filter=(Id%20eq%20%27chocolatey%27)%20and%20IsLatestVersion') -join '/'

# Reroute TEMP to a local location
New-Item $env:ALLUSERSPROFILE\choco-cache -ItemType Directory -Force
$env:TEMP = "$env:ALLUSERSPROFILE\choco-cache"

$localChocolateyPackageFilePath = Join-Path $env:TEMP 'chocolatey.nupkg'
$ChocoInstallPath = "$($env:SystemDrive)\ProgramData\Chocolatey\bin"
$env:ChocolateyInstall = "$($env:SystemDrive)\ProgramData\Chocolatey"
$env:Path += ";$ChocoInstallPath"
$DebugPreference = 'Continue';

# PowerShell v2/3 caches the output stream. Then it throws errors due
# to the FileStream not being what is expected. Fixes "The OS handle's
# position is not what FileStream expected. Do not use a handle
# simultaneously in one FileStream and in Win32 code or another
# FileStream."
function Fix-PowerShellOutputRedirectionBug {
$poshMajorVerion = $PSVersionTable.PSVersion.Major

if ($poshMajorVerion -lt 4) {
# http://www.leeholmes.com/blog/2008/07/30/workaround-the-os-handles-position-is-not-what-filestream-expected/ plus comments
$bindingFlags = [Reflection.BindingFlags] "Instance,NonPublic,GetField"
$objectRef = $host.GetType().GetField("externalHostRef", $bindingFlags).GetValue($host)
$bindingFlags = [Reflection.BindingFlags] "Instance,NonPublic,GetProperty"
$consoleHost = $objectRef.GetType().GetProperty("Value", $bindingFlags).GetValue($objectRef, @())
[void] $consoleHost.GetType().GetProperty("IsStandardOutputRedirected", $bindingFlags).GetValue($consoleHost, @())
$bindingFlags = [Reflection.BindingFlags] "Instance,NonPublic,GetField"
$field = $consoleHost.GetType().GetField("standardOutputWriter", $bindingFlags)
$field.SetValue($consoleHost, [Console]::Out)
[void] $consoleHost.GetType().GetProperty("IsStandardErrorRedirected", $bindingFlags).GetValue($consoleHost, @())
$field2 = $consoleHost.GetType().GetField("standardErrorWriter", $bindingFlags)
$field2.SetValue($consoleHost, [Console]::Error)
} catch {
Write-Output 'Unable to apply redirection fix.'


# Attempt to set highest encryption available for SecurityProtocol.
# PowerShell will not set this by default (until maybe .NET 4.6.x). This
# will typically produce a message for PowerShell v2 (just an info
# message though)
try {
# Set TLS 1.2 (3072), then TLS 1.1 (768), then TLS 1.0 (192)
# Use integers because the enumeration values for TLS 1.2 and TLS 1.1 won't
# exist in .NET 4.0, even though they are addressable if .NET 4.5+ is
# installed (.NET 4.5 is an in-place upgrade).
[System.Net.ServicePointManager]::SecurityProtocol = 3072 -bor 768 -bor 192
} catch {
Write-Output 'Unable to set PowerShell to use TLS 1.2 and TLS 1.1 due to old .NET Framework installed. If you see underlying connection closed or trust errors, you may need to upgrade to .NET Framework 4.5+ and PowerShell v3+.'

function Get-Downloader {
param (
$downloader = new-object System.Net.WebClient

$defaultCreds = [System.Net.CredentialCache]::DefaultCredentials
if (Test-Path -Path variable:repoCreds) {
Write-Debug "Using provided repository authentication credentials."
$downloader.Credentials = $repoCreds
} elseif ($defaultCreds -ne $null) {
Write-Debug "Using default repository authentication credentials."
$downloader.Credentials = $defaultCreds

$ignoreProxy = $env:chocolateyIgnoreProxy
if ($ignoreProxy -ne $null -and $ignoreProxy -eq 'true') {
Write-Debug 'Explicitly bypassing proxy due to user environment variable.'
$downloader.Proxy = [System.Net.GlobalProxySelection]::GetEmptyWebProxy()
} else {
# check if a proxy is required
$explicitProxy = $env:chocolateyProxyLocation
$explicitProxyUser = $env:chocolateyProxyUser
$explicitProxyPassword = $env:chocolateyProxyPassword
if ($explicitProxy -ne $null -and $explicitProxy -ne '') {
# explicit proxy
$proxy = New-Object System.Net.WebProxy($explicitProxy, $true)
if ($explicitProxyPassword -ne $null -and $explicitProxyPassword -ne '') {
$passwd = ConvertTo-SecureString $explicitProxyPassword -AsPlainText -Force
$proxy.Credentials = New-Object System.Management.Automation.PSCredential ($explicitProxyUser, $passwd)

Write-Debug "Using explicit proxy server '$explicitProxy'."
$downloader.Proxy = $proxy

} elseif (!$downloader.Proxy.IsBypassed($url)) {
# system proxy (pass through)
$creds = $defaultCreds
if ($creds -eq $null) {
Write-Debug 'Default credentials were null. Attempting backup method'
$cred = get-credential
$creds = $cred.GetNetworkCredential();

$proxyaddress = $downloader.Proxy.GetProxy($url).Authority
Write-Debug "Using system proxy server '$proxyaddress'."
$proxy = New-Object System.Net.WebProxy($proxyaddress)
$proxy.Credentials = $creds
$downloader.Proxy = $proxy

return $downloader

function Download-File {
param (
$downloader = Get-Downloader $url
$downloader.DownloadFile($url, $file)

function Download-Package {
param (
$downloader = Get-Downloader $packageODataSearchUrl

Write-Output "Querying latest package from $packageODataSearchUrl"
[xml]$pkg = $downloader.DownloadString($packageODataSearchUrl)
$packageDownloadUrl = $pkg.feed.entry.content.src

Write-Output "Downloading $packageDownloadUrl to $file"
$downloader.DownloadFile($packageDownloadUrl, $file)

function Install-ChocolateyFromPackage {
param (
[string]$chocolateyPackageFilePath = ''

if ($chocolateyPackageFilePath -eq $null -or $chocolateyPackageFilePath -eq '') {
throw "You must specify a local package to run the local install."

if (!(Test-Path($chocolateyPackageFilePath))) {
throw "No file exists at $chocolateyPackageFilePath"

$chocTempDir = Join-Path $env:TEMP "chocolatey"
$tempDir = Join-Path $chocTempDir "chocInstall"
if (![System.IO.Directory]::Exists($tempDir)) {[System.IO.Directory]::CreateDirectory($tempDir)}
$file = Join-Path $tempDir "chocolatey.zip"
Copy-Item $chocolateyPackageFilePath $file -Force

# unzip the package
Write-Output "Extracting $file to $tempDir..."
if ($unzipMethod -eq '7zip') {
$7zaExe = Join-Path $tempDir '7za.exe'
if (-Not (Test-Path ($7zaExe))) {
Write-Output 'Downloading 7-Zip commandline tool prior to extraction.'
# download 7zip
Download-File $7zipUrl "$7zaExe"

$params = "x -o`"$tempDir`" -bd -y `"$file`""
# use more robust Process as compared to Start-Process -Wait (which doesn't
# wait for the process to finish in PowerShell v3)
$process = New-Object System.Diagnostics.Process
$process.StartInfo = New-Object System.Diagnostics.ProcessStartInfo($7zaExe, $params)
$process.StartInfo.RedirectStandardOutput = $true
$process.StartInfo.UseShellExecute = $false
$process.StartInfo.WindowStyle = [System.Diagnostics.ProcessWindowStyle]::Hidden
$process.Start() | Out-Null
$exitCode = $process.ExitCode

$errorMessage = "Unable to unzip package using 7zip. Perhaps try setting `$env:chocolateyUseWindowsCompression = 'true' and call install again. Error:"
switch ($exitCode) {
0 { break }
1 { throw "$errorMessage Some files could not be extracted" }
2 { throw "$errorMessage 7-Zip encountered a fatal error while extracting the files" }
7 { throw "$errorMessage 7-Zip command line error" }
8 { throw "$errorMessage 7-Zip out of memory" }
255 { throw "$errorMessage Extraction cancelled by the user" }
default { throw "$errorMessage 7-Zip signalled an unknown error (code $exitCode)" }
} else {
if ($PSVersionTable.PSVersion.Major -lt 5) {
try {
$shellApplication = new-object -com shell.application
$zipPackage = $shellApplication.NameSpace($file)
$destinationFolder = $shellApplication.NameSpace($tempDir)
} catch {
throw "Unable to unzip package using built-in compression. Set `$env:chocolateyUseWindowsCompression = 'false' and call install again to use 7zip to unzip. Error: `n $_"
} else {
Expand-Archive -Path "$file" -DestinationPath "$tempDir" -Force

# Call Chocolatey install
Write-Output 'Installing chocolatey on this machine'
$toolsFolder = Join-Path $tempDir "tools"
$chocInstallPS1 = Join-Path $toolsFolder "chocolateyInstall.ps1"

& $chocInstallPS1

Write-Output 'Ensuring chocolatey commands are on the path'
$chocInstallVariableName = 'ChocolateyInstall'
$chocoPath = [Environment]::GetEnvironmentVariable($chocInstallVariableName)
if ($chocoPath -eq $null -or $chocoPath -eq '') {
$chocoPath = 'C:\ProgramData\Chocolatey'

$chocoExePath = Join-Path $chocoPath 'bin'

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

Write-Output 'Ensuring chocolatey.nupkg is in the lib folder'
$chocoPkgDir = Join-Path $chocoPath 'lib\chocolatey'
$nupkg = Join-Path $chocoPkgDir 'chocolatey.nupkg'
if (!(Test-Path $nupkg)) {
Write-Output 'Copying chocolatey.nupkg is in the lib folder'
if (![System.IO.Directory]::Exists($chocoPkgDir)) { [System.IO.Directory]::CreateDirectory($chocoPkgDir); }
Copy-Item "$file" "$nupkg" -Force -ErrorAction SilentlyContinue

# Idempotence - do not install Chocolatey if it is already installed
if (!(Test-Path $ChocoInstallPath)) {
# download the package to the local path
if (!(Test-Path $localChocolateyPackageFilePath)) {
Download-Package $searchUrl $localChocolateyPackageFilePath

# Install Chocolatey
Install-ChocolateyFromPackage $localChocolateyPackageFilePath
2. Make script accessible by internal url

Put the script somewhere internally that can be accessed by a url (like a raw/binary repository in Nexus, Artifactory, or ProGet). Do NOT put the script on a NuGet type repository (where your packages will be), create a new Raw/Binary repository.

3. Install/Deploy Chocolatey internally

Now you can do similar to the individual side, but your command will be something like:

Set-ExecutionPolicy Bypass -Scope Process -Force; iex ((New-Object System.Net.WebClient).DownloadString('INTERNAL REPO URL/ChocolateyInstall.ps1'))
3. Add the following to your playbook

- name: Ensure Chocolatey installed from internal repo
    name: chocolatey
    state: present
    source: INTERNAL REPO URL/ChocolateyInstall.ps1

See docs at https://docs.ansible.com/ansible/latest/modules/win_chocolatey_module.html.

# Note: `chocolateyDownloadUrl is completely different than normal
#  source locations. This is directly to the bare download url for the
#  chocolatey.nupkg, similar to what you see when you browse to
#  https://community.chocolatey.org/api/v2/package/chocolatey
node['chocolatey']['install_vars']['chocolateyDownloadUrl'] = 'INTERNAL REPO URL/check_this/chocolatey.VERSION.nupkg'
node['chocolatey']['upgrade'] = true
include_recipe 'chocolatey::default'

The install of Chocolatey is separate from the Chef built-in resources. You will need the Chocolatey Cookbook.

3. Add the following to your DSC script:

cChocoInstaller InstallChocolatey
  InstallDir            = "C:\ProgramData\chocolatey"
  ChocoInstallScriptUrl = "INTERNAL REPO URL/ChocolateyInstall.ps1"

Requires cChoco DSC Resource. See docs at https://github.com/chocolatey/cChoco.

## Note: `chocolatey_download_url is completely different than normal
##  source locations. This is directly to the bare download url for the
##  chocolatey.nupkg, similar to what you see when you browse to
##  https://community.chocolatey.org/api/v2/package/chocolatey
class {'chocolatey':
  chocolatey_download_url => 'INTERNAL REPO URL/check_this/chocolatey.VERSION.nupkg',
  use_7zip                => false,

Requires Puppet Chocolatey Provider module. See docs at https://forge.puppet.com/puppetlabs/chocolatey.

5. If applicable - Chocolatey configuration/installation

See infrastructure management matrix for Chocolatey configuration elements and examples.

Chocolatey Licensed Install:

Are you also installing a commercial edition of Chocolatey?

Please see Install the Licensed Edition.

Advanced Chocolatey Install:

Are you installing behind a proxy, need a completely offline install, or wanting to install a licenced edition of Chocolatey? Need even more options? Visit our Documentation or take our new Installation Course to help you get up and running with Chocolatey!

Option 1:
Read the Documentation
Read the Installation Docs
Option 2:
Take the step-by-step Installation Course
Take the Installation Course