Step 1: Review Your Packages

Step 2: Choose Your Integration Method

Step 3: Copy Your Script or Download Config

Option 1: Copy Script

Option 2: Download Config

Step 4: Setup Your Environment

1. Ensure you are set for organizational deployment

Please see the organizational deployment guide

2. Get the package into your environment

Option 1: Cached Package (Unreliable, Requires Internet - Same As Community)

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 https://community.chocolatey.org/api/v2/. 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 packages and push them to a repository
  Download Packages

Option 2: Internalized Package (Reliable, Scalable)

Open Source
- Download the packages:
  Download Packages
- Follow manual internalization instructions
Package Internalizer (C4B)
- Run: (additional options)
- For package and dependencies run:
- Automate package internalization

Step 5: Copy Your Script

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:

If Applicable - Chocolatey Configuration/Installation


## 1. REQUIREMENTS ##
### Here are the requirements necessary to ensure this is successful.

### a. Internal/Private Cloud Repository Set Up ###
#### You'll need an internal/private cloud repository you can use. These are
####  generally really quick to set up and there are quite a few options.
####  Chocolatey Software recommends Nexus, Artifactory Pro, or ProGet as they
####  are repository servers and will give you the ability to manage multiple
####  repositories and types from one server installation.

### b. Download Chocolatey Package and Put on Internal Repository ###
#### You need to have downloaded the Chocolatey package as well.
####  Please see https://chocolatey.org/install#organization

### c. Other Requirements ###

#### We initialize a few things that are needed by this script - there are no other requirements.
$ErrorActionPreference = "Stop"

#### Set TLS 1.2 (3072) as that is the minimum required by various up-to-date repositories.
#### Use integers because the enumeration value for TLS 1.2 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 = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072

#### We use this variable for future REST calls.
$RequestArguments = @{
    UseBasicParsing = $true
}

## 2. TOP LEVEL VARIABLES ##

### a. Your internal repository url (the main one). ###
####  Should be similar to what you see when you browse
#### to https://community.chocolatey.org/api/v2/
$NugetRepositoryUrl = "INTERNAL REPO URL"

### b. Internal Repository Credential ###
#### If required, add the repository access credential here
# $NugetRepositoryCredential = [PSCredential]::new(
#     "username",
#     ("password" | ConvertTo-SecureString -AsPlainText -Force)
# )
# $RequestArguments.Credential = $NugetRepositoryCredential

### c. Chocolatey nupkg download url ###
#### This url should result in an immediate download when you navigate to it
$ChocolateyDownloadUrl = "$($NugetRepositoryUrl.TrimEnd('/'))/package/chocolatey.2.4.3.nupkg"

### d. Chocolatey Central Management (CCM) ###
#### If using CCM to manage Chocolatey, add the following:
#### i. Endpoint URL for CCM
# $ChocolateyCentralManagementUrl = "https://chocolatey-central-management:24020/ChocolateyManagementService"

#### ii. If using a Client Salt, add it here
# $ChocolateyCentralManagementClientSalt = "clientsalt"

#### iii. If using a Service Salt, add it here
# $ChocolateyCentralManagementServiceSalt = "servicesalt"

## 3. ENSURE CHOCOLATEY IS INSTALLED ##
### Ensure Chocolatey is installed from your internal repository

#### Download the Nupkg, appending .zip to the filename to handle archive cmdlet limitations
if (-not (Get-Command choco.exe -ErrorAction SilentlyContinue)) {
    $TempDirectory = Join-Path $env:Temp "chocolateyInstall"
    if (-not (Test-Path $TempDirectory -PathType Container)) {
        $null = New-Item -Path $TempDirectory -ItemType Directory
    }
    $DownloadedNupkg = Join-Path $TempDirectory "$(Split-Path $ChocolateyDownloadUrl -Leaf).zip"
    Invoke-WebRequest -Uri $ChocolateyDownloadUrl -OutFile $DownloadedNupkg @RequestArguments

    #### Extract the Nupkg, and run the chocolateyInstall script
    if (Get-Command Microsoft.PowerShell.Archive\Expand-Archive -ErrorAction SilentlyContinue) {
        Microsoft.PowerShell.Archive\Expand-Archive -Path $DownloadedNupkg -DestinationPath $TempDirectory -Force
    } else {
        # PowerShell versions <4.0 do not have this function available
        try {
            $shellApplication = New-Object -ComObject Shell.Application
            $zipPackage = $shellApplication.NameSpace($DownloadedNupkg)
            $destinationFolder = $shellApplication.NameSpace($TempDirectory)
            $destinationFolder.CopyHere($zipPackage.Items(), 0x10)
        } catch {
            Write-Warning "Unable to unzip package using built-in compression."
            throw $_
        }
    }

    & $(Join-Path $TempDirectory "tools\chocolateyInstall.ps1")
}

if (-not (Get-Command choco.exe -ErrorAction SilentlyContinue)) {
    refreshenv
}

## 4. CONFIGURE CHOCOLATEY BASELINE ##
### a. FIPS Feature ###
#### If you need FIPS compliance - make this the first thing you configure
#### before you do any additional configuration or package installations
# choco feature enable -n useFipsCompliantChecksums

### b. Apply Recommended Configuration ###
#### Move cache location so Chocolatey is very deterministic about
#### cleaning up temporary data and the location is secured to admins
choco config set --name cacheLocation --value C:\ProgramData\chocolatey\cache

#### Increase timeout to at least 4 hours
choco config set --name commandExecutionTimeoutSeconds --value 14400

#### Turn off download progress when running choco through integrations
choco feature disable --name showDownloadProgress

### c. Sources ###
#### Remove the default community package repository source
choco source list --limitoutput | ConvertFrom-Csv -Header 'Name', 'Location' -Delimiter '|' | ForEach-Object {
    if ($_.Location -eq 'https://community.chocolatey.org/api/v2/') {
        choco source remove -n $_.Name
    }
}

#### Add internal default sources
#### You could have multiple sources here, so we will provide an example
#### of one using the remote repo variable here

#### NOTE: This EXAMPLE may require changes
if ($NugetRepositoryCredential) {
    choco source add --name ChocolateyInternal --source $NugetRepositoryUrl --user $NugetRepositoryCredential.UserName --password $NugetRepositoryCredential.GetNetworkCredential().Password --priority 1
} else {
    choco source add --name ChocolateyInternal --source $NugetRepositoryUrl --priority 1
}

### b. Keep Chocolatey Up To Date ###
#### Keep chocolatey up to date based on your internal source
#### You control the upgrades based on when you push an updated version
####  to your internal repository.
#### Note the source here is to the OData feed, similar to what you see
####  when you browse to https://community.chocolatey.org/api/v2/
choco upgrade chocolatey --confirm

## 5. ENSURE CHOCOLATEY FOR BUSINESS ##
### If you don't have Chocolatey for Business (C4B), you'll want to remove from here down.

### a. Ensure The License File Is Installed ###
#### Create a license package using script from https://docs.chocolatey.org/en-us/how-tos/setup-offline-installation#exercise-4-create-a-package-for-the-license
choco install chocolatey-license --source $NugetRepositoryUrl --confirm

### b. Disable The Licensed Source ###
#### The licensed source cannot be removed, so it must be disabled.
#### This must occur after the license has been set by the license package.
if ("chocolatey-license" -in (choco list --localonly --limitoutput | ConvertFrom-Csv -Header "Name" -Delimiter "|").Name) {
    choco source disable --name chocolatey.licensed
} else {
    Write-Warning "Not disabling 'chocolatey.licensed' feed, as Chocolatey-License has not been installed."
}

### c. Ensure Chocolatey Licensed Extension ###
#### You will have downloaded the licensed extension to your internal repository
#### as you have disabled the licensed repository in step 5b.

#### Ensure the chocolatey.extension package (aka Chocolatey Licensed Extension)
if ("chocolatey-license" -in (choco list --localonly --limitoutput | ConvertFrom-Csv -Header "Name" -Delimiter "|").Name) {
    choco install chocolatey.extension --source $NugetRepositoryUrl --confirm
} else {
    Write-Warning "Not installing 'chocolatey.extension', as Chocolatey-License has not been installed."
}

#### The Chocolatey Licensed Extension unlocks all of the following, which also have configuration/feature items available with them. You may want to visit the feature pages to see what you might want to also enable:
#### - Package Builder - https://docs.chocolatey.org/en-us/features/paid/package-builder
#### - Package Internalizer - https://docs.chocolatey.org/en-us/features/paid/package-internalizer
#### - Package Synchronization (3 components) - https://docs.chocolatey.org/en-us/features/paid/package-synchronization
#### - Package Reducer - https://docs.chocolatey.org/en-us/features/paid/package-reducer
#### - Package Audit - https://docs.chocolatey.org/en-us/features/paid/package-audit
#### - Package Throttle - https://docs.chocolatey.org/en-us/features/paid/package-throttle
#### - CDN Cache Access - https://docs.chocolatey.org/en-us/features/paid/private-cdn
#### - Branding - https://docs.chocolatey.org/en-us/features/paid/branding
#### - Self-Service Anywhere (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/self-service-anywhere
#### - Chocolatey Central Management (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/chocolatey-central-management
#### - Other - https://docs.chocolatey.org/en-us/features/paid/

### d. Ensure Self-Service Anywhere ###
#### If you have desktop clients where users are not administrators, you may
#### to take advantage of deploying and configuring Self-Service anywhere
choco feature disable --name showNonElevatedWarnings
choco feature enable --name useBackgroundService
choco feature enable --name useBackgroundServiceWithNonAdministratorsOnly
choco feature enable --name allowBackgroundServiceUninstallsFromUserInstallsOnly
choco config set --name allowedBackgroundServiceCommands --value "install,upgrade,uninstall"

### e. Ensure Chocolatey Central Management ###
#### If you want to manage and report on endpoints, you can set up and configure
### Central Management. There are multiple portions to manage, so you'll see
### a section on agents here along with notes on how to configure the server
### side components.
if ($ChocolateyCentralManagementUrl) {
    choco install chocolatey-agent --source $NugetRepositoryUrl --confirm
    choco config set --name CentralManagementServiceUrl --value $ChocolateyCentralManagementUrl
    if ($ChocolateyCentralManagementClientSalt) {
        choco config set --name centralManagementClientCommunicationSaltAdditivePassword --value $ChocolateyCentralManagementClientSalt
    }
    if ($ChocolateyCentralManagementServiceSalt) {
        choco config set --name centralManagementServiceCommunicationSaltAdditivePassword --value $ChocolateyCentralManagementServiceSalt
    }
    choco feature enable --name useChocolateyCentralManagement
    choco feature enable --name useChocolateyCentralManagementDeployments
}

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

If Applicable - Chocolatey Configuration/Installation


## 1. REQUIREMENTS ##
### Here are the requirements necessary to ensure this is successful.

### a. Internal/Private Cloud Repository Set Up ###
#### You'll need an internal/private cloud repository you can use. These are
####  generally really quick to set up and there are quite a few options.
####  Chocolatey Software recommends Nexus, Artifactory Pro, or ProGet as they
####  are repository servers and will give you the ability to manage multiple
####  repositories and types from one server installation.

### b. Download Chocolatey Package and Put on Internal Repository ###
#### You need to have downloaded the Chocolatey package as well.
####  Please see https://chocolatey.org/install#organization

### c. Other Requirements ###
#### i. chocolatey.chocolatey
##### You will require the chocolatey.chocolatey collection to be installed
##### on all machines using this playbook.
##### Please see https://github.com/chocolatey/chocolatey-ansible/#installing-the-collection-from-ansible-galaxy

- name: Install and Configure Chocolatey
  hosts: all

## 2. TOP LEVEL VARIABLES ##
  vars:

### a. Your internal repository url (the main one). ###
####  Should be similar to what you see when you browse
#### to https://community.chocolatey.org/api/v2/
    nuget_repository_url: INTERNAL REPO URL

### b. Internal Repository Credential ###
#### If required, add the repository access credential here and
#### uncomment lines with source_username and source_password below
#    nuget_repository_username: username
#    nuget_repository_password: password

### c. Chocolatey Central Management (CCM) ###
#### If using CCM to manage Chocolatey, add the following:
#### i. Endpoint URL for CCM
#    chocolatey_central_management_url: https://chocolatey-central-management:24020/ChocolateyManagementService

#### ii. If using a Client Salt, add it here
#    chocolatey_central_management_client_salt: clientsalt

#### iii. If using a Service Salt, add it here
#    chocolatey_central_management_service_salt: servicesalt

## 3. ENSURE CHOCOLATEY IS INSTALLED ##
### Ensure Chocolatey is installed from your internal repository

  tasks:
  - name: Install chocolatey
    win_chocolatey:
      name: chocolatey
      source: ""{{ nuget_repository_url }}""
      # source_username: ""{{ nuget_repository_username }}""
      # source_password: ""{{ nuget_repository_password }}""

## 4. CONFIGURE CHOCOLATEY BASELINE ##
### a. FIPS Feature ###
#### If you need FIPS compliance - make this the first thing you configure
#### before you do any additional configuration or package installations
#   - name: Enable FIPS compliance
#     win_chocolatey_feature:
#       name: useFipsCompliantChecksums
#       state: enabled

### b. Apply Recommended Configuration ###

#### Move cache location so Chocolatey is very deterministic about
#### cleaning up temporary data and the location is secured to admins
  - name: Set the cache location
    win_chocolatey_config:
      name: cacheLocation
      state: present
      value: C:\ProgramData\chocolatey\cache

#### Increase timeout to at least 4 hours
  - name: Set the command execution timeout
    win_chocolatey_config:
      name: commandExecutionTimeoutSeconds
      state: present
      value: 14400

#### Turn off download progress when running choco through integrations
  - name: Disable showing download progress
    win_chocolatey_feature:
      name: showDownloadProgress
      state: disabled

### c. Sources ###
#### Remove the default community package repository source
  - name: Remove Chocolatey Community Repository
    win_chocolatey_source:
      name: chocolatey
      state: absent

#### Add internal default sources
#### You could have multiple sources here, so we will provide an example
#### of one using the remote repo variable here
#### NOTE: This EXAMPLE may require changes
  - name: Add Internal Repository
    win_chocolatey_source:
      name: ChocolateyInternal
      state: present
      source: {{ nuget_repository_url }}
      # source_username: {{ nuget_repository_username }}
      # source_password: {{ nuget_repository_password }}
      priority: 1

### b. Keep Chocolatey Up To Date ###
#### Keep chocolatey up to date based on your internal source
#### You control the upgrades based on when you push an updated version
####  to your internal repository.
#### Note the source here is to the OData feed, similar to what you see
####  when you browse to https://community.chocolatey.org/api/v2/
  - name: Upgrade Chocolatey
    win_chocolatey:
      name: chocolatey
      state: latest

## 5. ENSURE CHOCOLATEY FOR BUSINESS ##
### If you don't have Chocolatey for Business (C4B), you'll want to remove from here down.
### a. Ensure The License File Is Installed ###
#### Create a license package using script from https://docs.chocolatey.org/en-us/how-tos/setup-offline-installation#exercise-4-create-a-package-for-the-license
  - name: Install Chocolatey License
    win_chocolatey:
      name: chocolatey-license
      source: ChocolateyInternal
      state: latest

### b. Disable The Licensed Source ###
#### The licensed source cannot be removed, so it must be disabled.
#### This must occur after the license has been set by the license package.
  - name: Disable Chocolatey Community Repository
    win_chocolatey_source:
      name: chocolatey.licensed
      state: disabled

### c. Ensure Chocolatey Licensed Extension ###
#### You will have downloaded the licensed extension to your internal repository
#### as you have disabled the licensed repository in step 5b.

#### Ensure the chocolatey.extension package (aka Chocolatey Licensed Extension)
  - name: Install Chocolatey Extension
    win_chocolatey:
      name: chocolatey.extension
      source: ChocolateyInternal
      state: latest

#### The Chocolatey Licensed Extension unlocks all of the following, which also have configuration/feature items available with them. You may want to visit the feature pages to see what you might want to also enable:
#### - Package Builder - https://docs.chocolatey.org/en-us/features/paid/package-builder
#### - Package Internalizer - https://docs.chocolatey.org/en-us/features/paid/package-internalizer
#### - Package Synchronization (3 components) - https://docs.chocolatey.org/en-us/features/paid/package-synchronization
#### - Package Reducer - https://docs.chocolatey.org/en-us/features/paid/package-reducer
#### - Package Audit - https://docs.chocolatey.org/en-us/features/paid/package-audit
#### - Package Throttle - https://docs.chocolatey.org/en-us/features/paid/package-throttle
#### - CDN Cache Access - https://docs.chocolatey.org/en-us/features/paid/private-cdn
#### - Branding - https://docs.chocolatey.org/en-us/features/paid/branding
#### - Self-Service Anywhere (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/self-service-anywhere
#### - Chocolatey Central Management (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/chocolatey-central-management
#### - Other - https://docs.chocolatey.org/en-us/features/paid/

### d. Ensure Self-Service Anywhere ###
#### If you have desktop clients where users are not administrators, you may
#### to take advantage of deploying and configuring Self-Service anywhere
  - name: Hide not-elevated warnings
    win_chocolatey_feature:
      name: showNonElevatedWarnings
      state: disabled

  - name: Use background mode for self-service
    win_chocolatey_feature:
      name: useBackgroundService
      state: enabled

  - name: Use background service for non-admins
    win_chocolatey_feature:
      name: useBackgroundServiceWithNonAdministratorsOnly
      state: enabled

  - name: Allow background uninstallation for user installs
    win_chocolatey_feature:
      name: allowBackgroundServiceUninstallsFromUserInstallsOnly
      state: enabled

  - name: Set allowed background service commands
    win_chocolatey_config:
      name: backgroundServiceAllowedCommands
      state: present
      value: install,upgrade,uninstall

### e. Ensure Chocolatey Central Management ###
#### If you want to manage and report on endpoints, you can set up and configure
### Central Management. There are multiple portions to manage, so you'll see
### a section on agents here along with notes on how to configure the server
### side components.
  - name: Install Chocolatey Agent
    when: chocolatey_central_management_url is defined
    win_chocolatey:
      name: chocolatey-agent
      source: ChocolateyInternal
      state: latest

  - name: Set the Central Management Service URL
    when: chocolatey_central_management_url is defined
    win_chocolatey_config:
      name: CentralManagementServiceUrl
      state: present
      value: {{ chocolatey_central_management_url }}

  - name: Set the Central Management Client Salt
    when: chocolatey_central_management_client_salt is defined
    win_chocolatey_config:
      name: centralManagementClientCommunicationSaltAdditivePassword
      state: present
      value: {{ chocolatey_central_management_client_salt }}

  - name: Set the Central Management Service Salt
    when: chocolatey_central_management_service_salt is defined
    win_chocolatey_config:
      name: centralManagementServiceCommunicationSaltAdditivePassword
      state: present
      value: {{ chocolatey_central_management_service_salt }}

  - name: Use Central Management
    when: chocolatey_central_management_url is defined
    win_chocolatey_feature:
      name: useChocolateyCentralManagement
      state: enabled

  - name: Use Central Management Deployments
    when: chocolatey_central_management_url is defined
    win_chocolatey_feature:
      name: useChocolateyCentralManagementDeployments
      state: enabled

See docs at https://docs.chef.io/resource_chocolatey_package.html.

If Applicable - Chocolatey Configuration/Installation


## 1. REQUIREMENTS ##
### Here are the requirements necessary to ensure this is successful.

### a. Internal/Private Cloud Repository Set Up ###
#### You'll need an internal/private cloud repository you can use. These are
####  generally really quick to set up and there are quite a few options.
####  Chocolatey Software recommends Nexus, Artifactory Pro, or ProGet as they
####  are repository servers and will give you the ability to manage multiple
####  repositories and types from one server installation.

### b. Download Chocolatey Package and Put on Internal Repository ###
#### You need to have downloaded the Chocolatey package as well.
####  Please see https://chocolatey.org/install#organization

### c. Other Requirements ###
#### The Chocolatey resources are available with any recent version of Chef.
#### We utilise the Chocolatey recipe to install the Chocolatey binaries.
include_recipe "chocolatey"

## 2. TOP LEVEL VARIABLES ##
### a. Your internal repository url (the main one). ###
####  Should be similar to what you see when you browse
#### to https://community.chocolatey.org/api/v2/
NugetRepositoryUrl = "INTERNAL REPO URL"

### b. Internal Repository Credential ###
#### If required, add the repository access credential here
# NugetRepositoryUsername = "username"
# NugetRepositoryPassword = "password"

### c. Chocolatey nupkg download url ###
#### This url should result in an immediate download when you navigate to it in
#### a web browser
ChocolateyNupkgUrl = "INTERNAL REPO URL/package/chocolatey.2.4.3.nupkg",

### d. Chocolatey Central Management (CCM) ###
#### If using CCM to manage Chocolatey, add the following:
#### i. Endpoint URL for CCM
# ChocolateyCentralManagementUrl = "https://chocolatey-central-management:24020/ChocolateyManagementService"

#### ii. If using a Client Salt, add it here
# ChocolateyCentralManagementClientSalt = "clientsalt"

#### iii. If using a Service Salt, add it here
# ChocolateyCentralManagementServiceSalt = "servicesalt"

## 3. ENSURE CHOCOLATEY IS INSTALLED ##
### Ensure Chocolatey is installed from your internal repository
node['chocolatey']['install vars'] = {
  'chocolateyDownloadUrl' => "#{ChocolateyNupkgUrl}",
}

## 4. CONFIGURE CHOCOLATEY BASELINE ##
### a. FIPS Feature ###
#### If you need FIPS compliance - make this the first thing you configure
#### before you do any additional configuration or package installations
# chocolatey_feature 'useFipsCompliantChecksums' do
#   action :enable
# end

### b. Apply Recommended Configuration ###

#### Move cache location so Chocolatey is very deterministic about
#### cleaning up temporary data and the location is secured to admins
chocolatey_config 'cacheLocation' do
  value 'C:\ProgramData\chocolatey\cache'
end

#### Increase timeout to at least 4 hours
chocolatey_config 'commandExecutionTimeoutSeconds' do
  value '14400'
end

#### Turn off download progress when running choco through integrations
chocolatey_feature 'showDownloadProgress' do
  action :disable
end

### c. Sources ###
#### Remove the default community package repository source
chocolatey_source 'chocolatey' do
  action :remove
end

#### Add internal default sources
#### You could have multiple sources here, so we will provide an example
#### of one using the remote repo variable here

#### NOTE: This EXAMPLE may require changes
chocolatey_source 'ChocolateyInternal' do
  source "#{NugetRepositoryUrl}"
  priority 1
  action   :add
end

execute 'ChocolateyInternal' do
  command "choco source add --name ChocolateyInternal -s #{NugetRepositoryUrl} -u=#{NugetRepositoryUsername} -p=#{NugetRepositoryPassword} --priority=1"
  only_if { NugetRepositoryUsername != nil || NugetRepositoryPassword != nil }
end

### b. Keep Chocolatey Up To Date ###
#### Keep chocolatey up to date based on your internal source
#### You control the upgrades based on when you push an updated version
####  to your internal repository.
#### Note the source here is to the OData feed, similar to what you see
####  when you browse to https://community.chocolatey.org/api/v2/
chocolatey_package 'chocolatey' do
  action :upgrade
  source "#{NugetRepositoryUrl}"
end

## 5. ENSURE CHOCOLATEY FOR BUSINESS ##
### If you don't have Chocolatey for Business (C4B), you'll want to remove from here down.

### a. Ensure The License File Is Installed ###
#### Create a license package using script from https://docs.chocolatey.org/en-us/how-tos/setup-offline-installation#exercise-4-create-a-package-for-the-license
chocolatey_package 'chocolatey-license' do
  action :install
  source "#{NugetRepositoryUrl}"
end

### b. Disable The Licensed Source ###
#### The licensed source cannot be removed, so it must be disabled.
#### This must occur after the license has been set by the license package.
chocolatey_source 'chocolatey.licensed' do
  action            :disable
end

### c. Ensure Chocolatey Licensed Extension ###
#### You will have downloaded the licensed extension to your internal repository
#### as you have disabled the licensed repository in step 5b.

#### Ensure the chocolatey.extension package (aka Chocolatey Licensed Extension)
chocolatey_package 'chocolatey.extention' do
  action     install
  source     "#{NugetRepositoryUrl}"
end

#### The Chocolatey Licensed Extension unlocks all of the following, which also have configuration/feature items available with them. You may want to visit the feature pages to see what you might want to also enable:
#### - Package Builder - https://docs.chocolatey.org/en-us/features/paid/package-builder
#### - Package Internalizer - https://docs.chocolatey.org/en-us/features/paid/package-internalizer
#### - Package Synchronization (3 components) - https://docs.chocolatey.org/en-us/features/paid/package-synchronization
#### - Package Reducer - https://docs.chocolatey.org/en-us/features/paid/package-reducer
#### - Package Audit - https://docs.chocolatey.org/en-us/features/paid/package-audit
#### - Package Throttle - https://docs.chocolatey.org/en-us/features/paid/package-throttle
#### - CDN Cache Access - https://docs.chocolatey.org/en-us/features/paid/private-cdn
#### - Branding - https://docs.chocolatey.org/en-us/features/paid/branding
#### - Self-Service Anywhere (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/self-service-anywhere
#### - Chocolatey Central Management (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/chocolatey-central-management
#### - Other - https://docs.chocolatey.org/en-us/features/paid/

### d. Ensure Self-Service Anywhere ###
#### If you have desktop clients where users are not administrators, you may
#### to take advantage of deploying and configuring Self-Service anywhere
chocolatey_feature 'showNonElevatedWarnings' do
  action :disable
end

chocolatey_feature 'useBackgroundService' do
  action :enable
end

chocolatey_feature 'useBackgroundServiceWithNonAdministratorsOnly' do
  action :enable
end

chocolatey_feature 'allowBackgroundServiceUninstallsFromUserInstallsOnly' do
  action :enable
end

chocolatey_config 'backgroundServiceAllowedCommands' do
  value 'install,upgrade,uninstall'
end

### e. Ensure Chocolatey Central Management ###
#### If you want to manage and report on endpoints, you can set up and configure
### Central Management. There are multiple portions to manage, so you'll see
### a section on agents here along with notes on how to configure the server
### side components.
chocolatey_package 'chocolatey-agent' do
  action     install
  source     "#{NugetRepositoryUrl}"
  # user       "#{NugetRepositoryUsername}"
  # password   "#{NugetRepositoryPassword}"
  only_if { ChocolateyCentralManagementUrl != nil }
end

chocolatey_config 'CentralManagementServiceUrl' do
  value  "#{ChocolateyCentralManagementUrl}"
  only_if { ChocolateyCentralManagementUrl != nil }
end

chocolatey_config 'centralManagementClientCommunicationSaltAdditivePassword' do
  value   "#{ChocolateyCentralManagementClientSalt}"
  only_if { ChocolateyCentralManagementClientSalt != nil }
end

chocolatey_config 'centralManagementServiceCommunicationSaltAdditivePassword' do
  value   "#{ChocolateyCentralManagementServiceSalt}"
  only_if { ChocolateyCentralManagementServiceSalt != nil }
end

chocolatey_feature 'useChocolateyCentralManagement' do
  action :enable
  only_if { ChocolateyCentralManagementUrl != nil }
end

chocolatey_feature 'useChocolateyCentralManagementDeployments' do
  action :enable
  only_if { ChocolateyCentralManagementUrl != nil }
end

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

If Applicable - Chocolatey Configuration/Installation


#requires -Modules cChoco
## 1. REQUIREMENTS ##
### Here are the requirements necessary to ensure this is successful.

### a. Internal/Private Cloud Repository Set Up ###
#### You'll need an internal/private cloud repository you can use. These are
####  generally really quick to set up and there are quite a few options.
####  Chocolatey Software recommends Nexus, Artifactory Pro, or ProGet as they
####  are repository servers and will give you the ability to manage multiple
####  repositories and types from one server installation.

### b. Download Chocolatey Package and Put on Internal Repository ###
#### You need to have downloaded the Chocolatey package as well.
####  Please see https://chocolatey.org/install#organization

### c. Other Requirements ###
#### i. Requires chocolatey\cChoco DSC module to be installed on the machine compiling the DSC manifest
#### NOTE: This will need to be installed before running the DSC portion of this script
if (-not (Get-Module cChoco -ListAvailable)) {
    $null = Install-PackageProvider -Name NuGet -MinimumVersion 2.8.5.201 -Force
    if (($PSGallery = Get-PSRepository -Name PSGallery).InstallationPolicy -ne "Trusted") {
        Set-PSRepository -Name PSGallery -InstallationPolicy Trusted
    }
    Install-Module -Name cChoco
    if ($PSGallery.InstallationPolicy -ne "Trusted") {
        Set-PSRepository -Name PSGallery -InstallationPolicy $PSGallery.InstallationPolicy
    }
}

#### ii. Requires a hosted copy of the install.ps1 script
##### This should be available to download without authentication.
##### The original script can be found here: https://community.chocolatey.org/install.ps1

Configuration ChocolateyConfig {
## 2. TOP LEVEL VARIABLES ##
    param(
### a. Your internal repository url (the main one). ###
####  Should be similar to what you see when you browse
#### to https://community.chocolatey.org/api/v2/
        $NugetRepositoryUrl      = "INTERNAL REPO URL",

### b. Chocolatey nupkg download url ###
#### This url should result in an immediate download when you navigate to it in
#### a web browser
        $ChocolateyNupkgUrl      = "INTERNAL REPO URL/package/chocolatey.2.4.3.nupkg",

### c. Internal Repository Credential ###
#### If required, add the repository access credential here
#        $NugetRepositoryCredential = [PSCredential]::new(
#            "username",
#            ("password" | ConvertTo-SecureString -AsPlainText -Force)
#        ),

### d. Install.ps1 URL
#### The path to the hosted install script:
        $ChocolateyInstallPs1Url = "https://community.chocolatey.org/install.ps1"

### e. Chocolatey Central Management (CCM) ###
#### If using CCM to manage Chocolatey, add the following:
#### i. Endpoint URL for CCM
#        $ChocolateyCentralManagementUrl = "https://chocolatey-central-management:24020/ChocolateyManagementService",

#### ii. If using a Client Salt, add it here
#        $ChocolateyCentralManagementClientSalt = "clientsalt",

#### iii. If using a Service Salt, add it here
#        $ChocolateyCentralManagementServiceSalt = "servicesalt"
    )
    Import-DscResource -ModuleName PSDesiredStateConfiguration
    Import-DscResource -ModuleName cChoco

    Node 'localhost' {
## 3. ENSURE CHOCOLATEY IS INSTALLED ##
### Ensure Chocolatey is installed from your internal repository
        Environment chocoDownloadUrl {
            Name  = "chocolateyDownloadUrl"
            Value = $ChocolateyNupkgUrl
        }

        cChocoInstaller installChocolatey {
            DependsOn = "[Environment]chocoDownloadUrl"
            InstallDir = Join-Path $env:ProgramData "chocolatey"
            ChocoInstallScriptUrl = $ChocolateyInstallPs1Url
        }

## 4. CONFIGURE CHOCOLATEY BASELINE ##
### a. FIPS Feature ###
#### If you need FIPS compliance - make this the first thing you configure
#### before you do any additional configuration or package installations
#        cChocoFeature featureFipsCompliance {
#            FeatureName = "useFipsCompliantChecksums"
#        }

### b. Apply Recommended Configuration ###

#### Move cache location so Chocolatey is very deterministic about
#### cleaning up temporary data and the location is secured to admins
        cChocoConfig cacheLocation {
            DependsOn  = "[cChocoInstaller]installChocolatey"
            ConfigName = "cacheLocation"
            Value      = "C:\ProgramData\chocolatey\cache"
        }

#### Increase timeout to at least 4 hours
        cChocoConfig commandExecutionTimeoutSeconds {
            DependsOn  = "[cChocoInstaller]installChocolatey"
            ConfigName = "commandExecutionTimeoutSeconds"
            Value      = 14400
        }

#### Turn off download progress when running choco through integrations
        cChocoFeature showDownloadProgress {
            DependsOn   = "[cChocoInstaller]installChocolatey"
            FeatureName = "showDownloadProgress"
            Ensure      = "Absent"
        }

### c. Sources ###
#### Remove the default community package repository source
        cChocoSource removeCommunityRepository {
            DependsOn  = "[cChocoInstaller]installChocolatey"
            Name       = "chocolatey"
            Ensure     = "Absent"
        }

#### Add internal default sources
#### You could have multiple sources here, so we will provide an example
#### of one using the remote repo variable here.
#### NOTE: This EXAMPLE may require changes
        cChocoSource addInternalSource {
            DependsOn  = "[cChocoInstaller]installChocolatey"
            Name        = "ChocolateyInternal"
            Source      = $NugetRepositoryUrl
            Credentials = $NugetRepositoryCredential
            Priority    = 1
        }

### b. Keep Chocolatey Up To Date ###
#### Keep chocolatey up to date based on your internal source
#### You control the upgrades based on when you push an updated version
####  to your internal repository.
#### Note the source here is to the OData feed, similar to what you see
####  when you browse to https://community.chocolatey.org/api/v2/
        cChocoPackageInstaller updateChocolatey {
            DependsOn   = "[cChocoSource]addInternalSource", "[cChocoSource]removeCommunityRepository"
            Name        = "chocolatey"
            AutoUpgrade = $true
        }

## 5. ENSURE CHOCOLATEY FOR BUSINESS ##
### If you don't have Chocolatey for Business (C4B), you'll want to remove from here down.

### a. Ensure The License File Is Installed ###
#### Create a license package using script from https://docs.chocolatey.org/en-us/how-tos/setup-offline-installation#exercise-4-create-a-package-for-the-license
        cChocoPackageInstaller chocolateyLicense {
            DependsOn = "[cChocoPackageInstaller]updateChocolatey"
            Name      = "chocolatey-license"
        }

### b. Disable The Licensed Source ###
#### The licensed source cannot be removed, so it must be disabled.
#### This must occur after the license has been set by the license package.
        Script disableLicensedSource {
            DependsOn  = "[cChocoPackageInstaller]chocolateyLicense"
            GetScript  = {
                $Source = choco source list --limitoutput | `
                    ConvertFrom-Csv -Delimiter '|' -Header Name, Source, Disabled | `
                    Where-Object Name -eq "chocolatey.licensed"

                return @{
                    Result = if ($Source) {
                        [bool]::Parse($Source.Disabled)
                    } else {
                        Write-Warning "Source 'chocolatey.licensed' was not present."
                        $true  # Source does not need disabling
                    }
                }
            }
            SetScript  = {
                $null = choco source disable --name "chocolatey.licensed"
            }
            TestScript = {
                $State = [ScriptBlock]::Create($GetScript).Invoke()
                return $State.Result
            }
        }

### c. Ensure Chocolatey Licensed Extension ###
#### You will have downloaded the licensed extension to your internal repository
#### as you have disabled the licensed repository in step 5b.

#### Ensure the chocolatey.extension package (aka Chocolatey Licensed Extension)
        cChocoPackageInstaller chocolateyLicensedExtension {
            DependsOn = "[Script]disableLicensedSource"
            Name      = "chocolatey.extension"
        }

#### The Chocolatey Licensed Extension unlocks all of the following, which also have configuration/feature items available with them. You may want to visit the feature pages to see what you might want to also enable:
#### - Package Builder - https://docs.chocolatey.org/en-us/features/paid/package-builder
#### - Package Internalizer - https://docs.chocolatey.org/en-us/features/paid/package-internalizer
#### - Package Synchronization (3 components) - https://docs.chocolatey.org/en-us/features/paid/package-synchronization
#### - Package Reducer - https://docs.chocolatey.org/en-us/features/paid/package-reducer
#### - Package Audit - https://docs.chocolatey.org/en-us/features/paid/package-audit
#### - Package Throttle - https://docs.chocolatey.org/en-us/features/paid/package-throttle
#### - CDN Cache Access - https://docs.chocolatey.org/en-us/features/paid/private-cdn
#### - Branding - https://docs.chocolatey.org/en-us/features/paid/branding
#### - Self-Service Anywhere (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/self-service-anywhere
#### - Chocolatey Central Management (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/chocolatey-central-management
#### - Other - https://docs.chocolatey.org/en-us/features/paid/

### d. Ensure Self-Service Anywhere ###
#### If you have desktop clients where users are not administrators, you may
#### to take advantage of deploying and configuring Self-Service anywhere
        cChocoFeature hideElevatedWarnings {
            DependsOn   = "[cChocoPackageInstaller]chocolateyLicensedExtension"
            FeatureName = "showNonElevatedWarnings"
            Ensure      = "Absent"
        }

        cChocoFeature useBackgroundService {
            DependsOn   = "[cChocoPackageInstaller]chocolateyLicensedExtension"
            FeatureName = "useBackgroundService"
            Ensure      = "Present"
        }

        cChocoFeature useBackgroundServiceWithNonAdmins {
            DependsOn   = "[cChocoPackageInstaller]chocolateyLicensedExtension"
            FeatureName = "useBackgroundServiceWithNonAdministratorsOnly"
            Ensure      = "Present"
        }

        cChocoFeature useBackgroundServiceUninstallsForUserInstalls {
            DependsOn   = "[cChocoPackageInstaller]chocolateyLicensedExtension"
            FeatureName = "allowBackgroundServiceUninstallsFromUserInstallsOnly"
            Ensure      = "Present"
        }

        cChocoConfig allowedBackgroundServiceCommands {
            DependsOn   = "[cChocoFeature]useBackgroundService"
            ConfigName = "backgroundServiceAllowedCommands"
            Value       = "install,upgrade,uninstall"
        }

### e. Ensure Chocolatey Central Management ###
#### If you want to manage and report on endpoints, you can set up and configure
### Central Management. There are multiple portions to manage, so you'll see
### a section on agents here along with notes on how to configure the server
### side components.
        if ($ChocolateyCentralManagementUrl) {
            cChocoPackageInstaller chocolateyAgent {
                DependsOn = "[cChocoPackageInstaller]chocolateyLicensedExtension"
                Name      = "chocolatey-agent"
            }

            cChocoConfig centralManagementServiceUrl {
                DependsOn   = "[cChocoPackageInstaller]chocolateyAgent"
                ConfigName = "CentralManagementServiceUrl"
                Value       = $ChocolateyCentralManagementUrl
            }

            if ($ChocolateyCentralManagementClientSalt) {
                cChocoConfig centralManagementClientSalt {
                    DependsOn  = "[cChocoPackageInstaller]chocolateyAgent"
                    ConfigName = "centralManagementClientCommunicationSaltAdditivePassword"
                    Value      = $ChocolateyCentralManagementClientSalt
                }
            }

            if ($ChocolateyCentralManagementServiceSalt) {
                cChocoConfig centralManagementServiceSalt {
                    DependsOn  = "[cChocoPackageInstaller]chocolateyAgent"
                    ConfigName = "centralManagementServiceCommunicationSaltAdditivePassword"
                    Value      = $ChocolateyCentralManagementServiceSalt
                }
            }

            cChocoFeature useCentralManagement {
                DependsOn   = "[cChocoPackageInstaller]chocolateyAgent"
                FeatureName = "useChocolateyCentralManagement"
                Ensure      = "Present"
            }

            cChocoFeature useCentralManagementDeployments {
                DependsOn   = "[cChocoPackageInstaller]chocolateyAgent"
                FeatureName = "useChocolateyCentralManagementDeployments"
                Ensure      = "Present"
            }
        }
    }
}

# If working this into an existing configuration with a good method for
$ConfigData = @{
    AllNodes = @(
        @{
            NodeName                    = "localhost"
            PSDscAllowPlainTextPassword = $true
        }
    )
}

try {
    Push-Location $env:Temp
    $Config = ChocolateyConfig -ConfigurationData $ConfigData
    Start-DscConfiguration -Path $Config.PSParentPath -Wait -Verbose -Force
} finally {
    Pop-Location
}

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

If Applicable - Chocolatey Configuration/Installation


## 1. REQUIREMENTS ##
### Here are the requirements necessary to ensure this is successful.

### a. Internal/Private Cloud Repository Set Up ###
#### You'll need an internal/private cloud repository you can use. These are
####  generally really quick to set up and there are quite a few options.
####  Chocolatey Software recommends Nexus, Artifactory Pro, or ProGet as they
####  are repository servers and will give you the ability to manage multiple
####  repositories and types from one server installation.

### b. Download Chocolatey Package and Put on Internal Repository ###
#### You need to have downloaded the Chocolatey package as well.
####  Please see https://chocolatey.org/install#organization

### c. Other Requirements ###
#### i. Requires puppetlabs/chocolatey module
####  See https://forge.puppet.com/puppetlabs/chocolatey


## 2. TOP LEVEL VARIABLES ##
### a. Your internal repository url (the main one). ###
####  Should be similar to what you see when you browse
#### to https://community.chocolatey.org/api/v2/
$_repository_url = 'INTERNAL REPO URL'

### b. Chocolatey nupkg download url ###
#### This url should result in an immediate download when you navigate to it in
#### a web browser
$_choco_download_url = 'INTERNAL REPO URL/package/chocolatey.2.4.3.nupkg'

### c. Chocolatey Central Management (CCM) ###
#### If using CCM to manage Chocolatey, add the following:
#### i. Endpoint URL for CCM
# $_chocolatey_central_management_url = 'https://chocolatey-central-management:24020/ChocolateyManagementService'

#### ii. If using a Client Salt, add it here
# $_chocolatey_central_management_client_salt = "clientsalt"

#### iii. If using a Service Salt, add it here
# $_chocolatey_central_management_service_salt = 'servicesalt'


## 3. ENSURE CHOCOLATEY IS INSTALLED ##
### Ensure Chocolatey is installed from your internal repository
### 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 => $_choco_download_url,
  use_7zip                => false,
}


## 4. CONFIGURE CHOCOLATEY BASELINE ##
### a. FIPS Feature ###
#### If you need FIPS compliance - make this the first thing you configure
#### before you do any additional configuration or package installations

#chocolateyfeature {'useFipsCompliantChecksums':
#  ensure => enabled,
#}

### b. Apply Recommended Configuration ###

#### Move cache location so Chocolatey is very deterministic about
#### cleaning up temporary data and the location is secured to admins
chocolateyconfig {'cacheLocation':
  value => 'C:\ProgramData\chocolatey\cache',
}

#### Increase timeout to at least 4 hours
chocolateyconfig {'commandExecutionTimeoutSeconds':
  value => '14400',
}

#### Turn off download progress when running choco through integrations
chocolateyfeature {'showDownloadProgress':
  ensure => disabled,
}

### c. Sources ###
#### Remove the default community package repository source
chocolateysource {'chocolatey':
  ensure   => absent,
  location => 'https://community.chocolatey.org/api/v2/',
}

#### Add internal default sources
#### You could have multiple sources here, so we will provide an example
#### of one using the remote repo variable here

#### NOTE: This EXAMPLE requires changes
chocolateysource {'internal_chocolatey':
  ensure             => present,
  location           => $_repository_url,
  priority           => 1,
  username           => 'optional',
  password           => 'optional,not ensured',
  bypass_proxy       => true,
  admin_only         => false,
  allow_self_service => false,
}

### b. Keep Chocolatey Up To Date ###
#### Keep chocolatey up to date based on your internal source
#### You control the upgrades based on when you push an updated version
####  to your internal repository.
#### Note the source here is to the OData feed, similar to what you see
####  when you browse to https://community.chocolatey.org/api/v2/

package {'chocolatey':
  ensure   => latest,
  provider => chocolatey,
  source   => $_repository_url,
}


## 5. ENSURE CHOCOLATEY FOR BUSINESS ##
### If you don't have Chocolatey for Business (C4B), you'll want to remove from here down.

### a. Ensure The License File Is Installed ###
#### Create a license package using script from https://docs.chocolatey.org/en-us/guides/organizations/organizational-deployment-guide#exercise-4-create-a-package-for-the-license

# TODO: Add resource for installing/ensuring the chocolatey-license package
package {'chocolatey-license':
  ensure   => latest,
  provider => chocolatey,
  source   => $_repository_url,
}

### b. Disable The Licensed Source ###
#### The licensed source cannot be removed, so it must be disabled.
#### This must occur after the license has been set by the license package.
## Disabled sources still need all other attributes until
## https://tickets.puppetlabs.com/browse/MODULES-4449 is resolved.
## Password is necessary with user, but not ensurable, so it should not
## matter what it is set to here. If you ever do get into trouble here,
## the password is your license GUID.
chocolateysource {'chocolatey.licensed':
  ensure   => disabled,
  priority => '10',
  user     => 'customer',
  password => '1234',
  require  => Package['chocolatey-license'],
}

### c. Ensure Chocolatey Licensed Extension ###
#### You will have downloaded the licensed extension to your internal repository
#### as you have disabled the licensed repository in step 5b.

#### Ensure the chocolatey.extension package (aka Chocolatey Licensed Extension)
package {'chocolatey.extension':
  ensure   => latest,
  provider => chocolatey,
  source   => $_repository_url,
  require  => Package['chocolatey-license'],
}

#### The Chocolatey Licensed Extension unlocks all of the following, which also have configuration/feature items available with them. You may want to visit the feature pages to see what you might want to also enable:
#### - Package Builder - https://docs.chocolatey.org/en-us/features/paid/package-builder
#### - Package Internalizer - https://docs.chocolatey.org/en-us/features/paid/package-internalizer
#### - Package Synchronization (3 components) - https://docs.chocolatey.org/en-us/features/paid/package-synchronization
#### - Package Reducer - https://docs.chocolatey.org/en-us/features/paid/package-reducer
#### - Package Audit - https://docs.chocolatey.org/en-us/features/paid/package-audit
#### - Package Throttle - https://docs.chocolatey.org/en-us/features/paid/package-throttle
#### - CDN Cache Access - https://docs.chocolatey.org/en-us/features/paid/private-cdn
#### - Branding - https://docs.chocolatey.org/en-us/features/paid/branding
#### - Self-Service Anywhere (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/self-service-anywhere
#### - Chocolatey Central Management (more components will need to be installed and additional configuration will need to be set) - https://docs.chocolatey.org/en-us/features/paid/chocolatey-central-management
#### - Other - https://docs.chocolatey.org/en-us/features/paid/

### d. Ensure Self-Service Anywhere ###
#### If you have desktop clients where users are not administrators, you may
#### to take advantage of deploying and configuring Self-Service anywhere
chocolateyfeature {'showNonElevatedWarnings':
  ensure => disabled,
}

chocolateyfeature {'useBackgroundService':
  ensure => enabled,
}

chocolateyfeature {'useBackgroundServiceWithNonAdministratorsOnly':
  ensure => enabled,
}

chocolateyfeature {'allowBackgroundServiceUninstallsFromUserInstallsOnly':
  ensure => enabled,
}

chocolateyconfig {'backgroundServiceAllowedCommands':
  value => 'install,upgrade,uninstall',
}

### e. Ensure Chocolatey Central Management ###
#### If you want to manage and report on endpoints, you can set up and configure
### Central Management. There are multiple portions to manage, so you'll see
### a section on agents here along with notes on how to configure the server
### side components.
if $_chocolatey_central_management_url {
  package {'chocolatey-agent':
    ensure   => latest,
    provider => chocolatey,
    source   => $_repository_url,
    require  => Package['chocolatey-license'],
  }

  chocolateyconfig {'CentralManagementServiceUrl':
    value   => $_chocolatey_central_management_url,
  }

  if $_chocolatey_central_management_client_salt {
    chocolateyconfig {'centralManagementClientCommunicationSaltAdditivePassword':
      value => $_chocolatey_central_management_client_salt,
    }
  }

  if $_chocolatey_central_management_service_salt {
    chocolateyconfig {'centralManagementClientCommunicationSaltAdditivePassword':
      value => $_chocolatey_central_management_client_salt,
    }
  }

  chocolateyfeature {'useChocolateyCentralManagement':
    ensure  => enabled,
    require => Package['chocolatey-agent'],
  }

  chocolateyfeature {'useChocolateyCentralManagementDeployments':
    ensure  => enabled,
    require => Package['chocolatey-agent'],
  }
}

Need Help? View our docs or file an issue.

There is already a version of this package in your Script Builder

Current Version	New Version

Downloads:

275,923

Downloads of v 1.6.0:

806

Last Update:

24 Mar 2021

Package Maintainer(s):

Software Author(s):

Tailscale
Inc.

Tags:

tailscale wireguard vpn

Tailscale

This is not the latest version of Tailscale available.

1.6.0 | Updated: 24 Mar 2021

Downloads:

275,923

Downloads of v 1.6.0:

806

Maintainer(s):

Software Author(s):

Tailscale
Inc.

Tags:

tailscale wireguard vpn

Tailscale 1.6.0

This is not the latest version of Tailscale available.

Legal Disclaimer: Neither this package nor Chocolatey Software, Inc. are affiliated with or endorsed by Tailscale, Inc. The inclusion of Tailscale, Inc. trademark(s), if any, upon this webpage is solely to identify Tailscale, Inc. goods or services and not for commercial purposes.

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We recommend clicking the "Details" link to make your own decision on installing this package.

Details

Learn More

Deployment Method: Individual Install, Upgrade, & Uninstall

To install Tailscale, run the following command from the command line or from PowerShell:

To upgrade Tailscale, run the following command from the command line or from PowerShell:

To uninstall Tailscale, run the following command from the command line or from PowerShell:

NOTE

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

1. Enter Your Internal Repository Url

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

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

Option 1: Cached Package (Unreliable, Requires Internet - Same As Community)

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 https://community.chocolatey.org/api/v2/. 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

Option 2: Internalized Package (Reliable, Scalable)

Open Source
- Download the package:
  Download
- Follow manual internalization instructions

Package Internalizer (C4B)

Run: (additional options)

choco download tailscale --internalize --version=1.6.0 --source=https://community.chocolatey.org/api/v2/

For package and dependencies run:

choco push --source="'INTERNAL REPO URL'"

Automate package internalization

3. Copy Your Script

choco upgrade tailscale -y --source="'INTERNAL REPO URL'" --version="'1.6.0'" [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 tailscale -y --source="'INTERNAL REPO URL'" --version="'1.6.0'" 
$exitCode = $LASTEXITCODE

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

Exit $exitCode


- name: Install tailscale
  win_chocolatey:
    name: tailscale
    version: '1.6.0'
    source: INTERNAL REPO URL
    state: present

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


chocolatey_package 'tailscale' do
  action    :install
  source   'INTERNAL REPO URL'
  version  '1.6.0'
end

See docs at https://docs.chef.io/resource_chocolatey_package.html.


cChocoPackageInstaller tailscale
{
    Name     = "tailscale"
    Version  = "1.6.0"
    Source   = "INTERNAL REPO URL"
}

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


package { 'tailscale':
  ensure   => '1.6.0',
  provider => 'chocolatey',
  source   => 'INTERNAL REPO URL',
}

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

4. If applicable - Chocolatey configuration/installation

See infrastructure management matrix for Chocolatey configuration elements and examples.

NOTE

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Package Approved

This package was approved as a trusted package on 26 Mar 2021.

Description

The Tailscale client allows you to connect all your devices using WireGuard®, without the hassle. Tailscale makes it as easy as installing an app and signing in.

WireGuard is a registered trademark of Jason A. Donenfeld.

Files

tools\chocolateybeforemodify.ps1

# This runs in 0.9.10+ before upgrade and uninstall.
# Use this file to do things like stop services prior to upgrade or uninstall.

Stop-Service -Name "Tailscale IPN"

tools\chocolateyinstall.ps1

$ErrorActionPreference = 'Stop';

$toolsDir = "$(Split-Path -parent $MyInvocation.MyCommand.Definition)"

Get-ChildItem -Path "$toolsDir\tailscale.cer" | Import-Certificate -CertStoreLocation Cert:\LocalMachine\TrustedPublisher

$url = 'https://pkgs.tailscale.com/stable/tailscale-ipn-setup-1.6.0.exe'


$packageArgs = @{
  packageName    = $env:ChocolateyPackageName
  unzipLocation  = $toolsDir
  fileType       = 'exe'
  url            = $url

  softwareName   = 'Tailscale'

  checksum       = '87a8217c2288f961f0d77360bcf3006bf99bb17a076795ad99b7945b78d61a0e'
  checksumType   = 'sha256'

  silentArgs     = '/S'
  validExitCodes = @(0)
}

Install-ChocolateyPackage @packageArgs

tools\chocolateyuninstall.ps1

$ErrorActionPreference = 'Stop';
$packageArgs = @{
  packageName   = $env:ChocolateyPackageName
  softwareName  = 'Tailscale IPN'
  fileType      = 'exe'
  silentArgs   = '/S'
  validExitCodes= @(0)
}

$uninstalled = $false
[array]$key = Get-UninstallRegistryKey -SoftwareName $packageArgs['softwareName']

if ($key.Count -eq 1) {
  $key | % { 
    $packageArgs['file'] = "$($_.UninstallString)"
    
    if ($packageArgs['fileType'] -eq 'MSI') {
      $packageArgs['silentArgs'] = "$($_.PSChildName) $($packageArgs['silentArgs'])"
      
      $packageArgs['file'] = ''
    } else {
    }

    Uninstall-ChocolateyPackage @packageArgs
  }
} elseif ($key.Count -eq 0) {
  Write-Warning "$packageName has already been uninstalled by other means."
} elseif ($key.Count -gt 1) {
  Write-Warning "$($key.Count) matches found!"
  Write-Warning "To prevent accidental data loss, no programs will be uninstalled."
  Write-Warning "Please alert package maintainer the following keys were matched:"
  $key | ForEach-Object {Write-Warning "- $($_.DisplayName)"}
}

# Remove device driver certificate.
Get-ChildItem Cert:\LocalMachine\TrustedPublisher | Where-Object { $_.thumbprint -eq 'DEE8D4EF882C2C255D879EF109C1DB9CF743476E' } | Remove-Item

tools\tailscale.cer

Virus Scan Results

tailscale.1.6.0.nupkg (30fa48b9f659) - ## / 62
tailscale-ipn-setup-1.6.0.exe (87a8217c2288) - ## / 68

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.

Version History

Version	Downloads	Last Updated	Status
Tailscale 1.82.5	7578	Tuesday, April 22, 2025	Approved
Tailscale 1.82.0	7296	Monday, March 31, 2025	Approved
Tailscale 1.80.2	15453	Tuesday, February 18, 2025	Approved
Tailscale 1.78.1	20692	Wednesday, December 11, 2024	Approved
Tailscale 1.76.6	11886	Thursday, November 7, 2024	Approved
Tailscale 1.76.3	7241	Wednesday, October 23, 2024	Approved
Tailscale 1.74.0	12415	Thursday, September 12, 2024	Approved
Tailscale 1.72.0	6442	Monday, August 19, 2024	Approved
Tailscale 1.70.0	8774	Wednesday, July 17, 2024	Approved
Tailscale 1.68.1	7963	Friday, June 14, 2024	Approved
Tailscale 1.68.0	1797	Wednesday, June 12, 2024	Approved
Tailscale 1.66.4	5773	Tuesday, May 21, 2024	Approved
Tailscale 1.66.3	2751	Wednesday, May 15, 2024	Approved
Tailscale 1.66.0	3011	Wednesday, May 8, 2024	Approved
Tailscale 1.64.2	5185	Wednesday, April 17, 2024	Approved
Tailscale 1.64.0	2851	Thursday, April 11, 2024	Approved
Tailscale 1.62.1	4071	Tuesday, March 26, 2024	Approved
Tailscale 1.62.0	3686	Wednesday, March 13, 2024	Approved
Tailscale 1.60.1	3217	Thursday, February 29, 2024	Approved
Tailscale 1.60.0	3751	Friday, February 16, 2024	Approved
Tailscale 1.58.2	6095	Tuesday, January 23, 2024	Approved
Tailscale 1.58.0	2803	Friday, January 19, 2024	Approved
Tailscale 1.56.1	8669	Friday, December 15, 2023	Approved
Tailscale 1.56.0	1682	Wednesday, December 13, 2023	Approved
Tailscale 1.54.1	4115	Thursday, November 30, 2023	Approved
Tailscale 1.54.0	3690	Wednesday, November 15, 2023	Approved
Tailscale 1.52.1	3886	Thursday, November 2, 2023	Approved
Tailscale 1.50.0	16517	Monday, September 25, 2023	Approved
Tailscale 1.48.2	4871	Tuesday, September 12, 2023	Approved
Tailscale 1.48.1	5859	Monday, August 21, 2023	Approved
Tailscale 1.48.0	2039	Wednesday, August 16, 2023	Approved
Tailscale 1.46.1	5309	Wednesday, July 26, 2023	Approved
Tailscale 1.46.0	3492	Wednesday, July 19, 2023	Approved
Tailscale 1.44.2	1110	Tuesday, July 18, 2023	Approved
Tailscale 1.44.0	4097	Wednesday, June 21, 2023	Approved
Tailscale 1.42.0	5260	Wednesday, May 24, 2023	Approved
Tailscale 1.40.1	2908	Thursday, May 11, 2023	Approved
Tailscale 1.40.0	2718	Thursday, April 27, 2023	Approved
Tailscale 1.38.4	3100	Wednesday, April 5, 2023	Approved
Tailscale 1.38.3	1490	Thursday, March 30, 2023	Approved
Tailscale 1.38.1	2035	Friday, March 17, 2023	Approved
Tailscale 1.36.2	2579	Sunday, February 26, 2023	Approved
Tailscale 1.36.0	4636	Wednesday, January 25, 2023	Approved
Tailscale 1.34.2	1724	Monday, January 16, 2023	Approved
Tailscale 1.34.1	2767	Wednesday, December 14, 2022	Approved
Tailscale 1.34.0	1050	Saturday, December 10, 2022	Approved
Tailscale 1.32.3	2335	Monday, November 21, 2022	Approved
Tailscale 1.32.2	1250	Sunday, November 6, 2022	Approved
Tailscale 1.32.1	1130	Monday, October 24, 2022	Approved
Tailscale 1.30.2	1901	Friday, September 16, 2022	Approved
Tailscale 1.30.1	894	Friday, September 9, 2022	Approved
Tailscale 1.28.0	2227	Tuesday, July 19, 2022	Approved
Tailscale 1.26.0	1689	Tuesday, June 7, 2022	Approved
Tailscale 1.24.1	1194	Thursday, April 28, 2022	Approved
Tailscale 1.22.1	1481	Tuesday, March 15, 2022	Approved
Tailscale 1.20.4	863	Saturday, February 19, 2022	Approved
Tailscale 1.20.2	917	Saturday, January 22, 2022	Approved
Tailscale 1.18.2	962	Thursday, December 16, 2021	Approved
Tailscale 1.18.0	893	Friday, November 19, 2021	Approved
Tailscale 1.16.2	627	Saturday, October 30, 2021	Approved
Tailscale 1.16.1	113	Friday, October 29, 2021	Approved
Tailscale 1.16.0	568	Monday, October 11, 2021	Approved
Tailscale 1.14.4	487	Wednesday, September 29, 2021	Approved
Tailscale 1.14.0	604	Tuesday, August 24, 2021	Approved
Tailscale 1.12.3	186	Saturday, August 21, 2021	Approved
Tailscale 1.12.1	577	Wednesday, July 28, 2021	Approved
Tailscale 1.10.2	439	Friday, July 16, 2021	Approved
Tailscale 1.10.1	261	Thursday, July 8, 2021	Approved
Tailscale 1.10.0	431	Sunday, June 27, 2021	Approved
Tailscale 1.8.7	368	Monday, June 14, 2021	Approved
Tailscale 1.8.5	422	Monday, May 24, 2021	Approved
Tailscale 1.8.3	190	Wednesday, May 19, 2021	Approved
Tailscale 1.8.0	209	Thursday, May 6, 2021	Approved
Tailscale 1.6.0	806	Wednesday, March 24, 2021	Approved
Tailscale 1.4.6	201	Monday, March 15, 2021	Approved
Tailscale 1.4.5	239	Wednesday, February 24, 2021	Approved
Tailscale 1.4.4	204	Monday, February 15, 2021	Approved
Tailscale 1.4.0	268	Thursday, January 28, 2021	Approved
Tailscale 1.3.147	263	Tuesday, January 5, 2021	Approved
Tailscale 1.2.9	267	Monday, November 30, 2020	Approved
Tailscale 1.2.5	215	Monday, November 16, 2020	Approved
Tailscale 1.0.4	207	Thursday, October 22, 2020	Approved
Tailscale 1.0.3	362	Tuesday, August 4, 2020	Approved
Tailscale 0.100.0.107	182	Tuesday, July 28, 2020	Approved
Tailscale 0.99.0	170	Thursday, July 9, 2020	Approved
Tailscale 0.98.0	203	Sunday, June 7, 2020	Approved

Dependencies

This package has no dependencies.

Discussion for the Tailscale Package

Ground Rules:

This discussion is only about Tailscale and the Tailscale 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 Tailscale, 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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24 Mar 2021

Tailscale

Tailscale 1.6.0

Some Checks Have Failed or Are Not Yet Complete

Deployment Method: Individual Install, Upgrade, & Uninstall

Deployment Method:

1. Enter Your Internal Repository Url

2. Setup Your Environment

1. Ensure you are set for organizational deployment

2. Get the package into your environment

3. Copy Your Script

4. If applicable - Chocolatey configuration/installation

Ground Rules: