Calling All Chocolatiers! Whipping Up Windows Automation with Chocolatey Central Management

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 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

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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 1.30.1:


Last Update:

09 Sep 2022

Package Maintainer(s):

Software Author(s):

  • Tailscale
  • Inc.


tailscale wireguard vpn


This is not the latest version of Tailscale available.

  • 1
  • 2
  • 3

1.30.1 | Updated: 09 Sep 2022



Downloads of v 1.30.1:


Software Author(s):

  • Tailscale
  • Inc.

Tailscale 1.30.1

This is not the latest version of Tailscale available.

  • 1
  • 2
  • 3

All Checks are Passing

3 Passing Tests

Validation Testing Passed

Verification Testing Passed


Scan Testing Successful:

No detections found in any package files

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:


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 tailscale -y --source="'INTERNAL REPO URL'" --version="'1.30.1'" [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="'1.30.1'" 

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

Exit $exitCode

- name: Install tailscale
    name: tailscale
    version: '1.30.1'
    state: present

See docs at

chocolatey_package 'tailscale' do
  action    :install
  source   'INTERNAL REPO URL'
  version  '1.30.1'

See docs at

cChocoPackageInstaller tailscale
    Name     = "tailscale"
    Version  = "1.30.1"
    Source   = "INTERNAL REPO URL"

Requires cChoco DSC Resource. See docs at

package { 'tailscale':
  ensure   => '1.30.1',
  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.


Private CDN cached downloads available for licensed customers. Never experience 404 breakages again! Learn more...

Package Approved

This package was approved as a trusted package on 09 Sep 2022.


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.

$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
$ErrorActionPreference = 'Stop';

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

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

$url = ''

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

  softwareName   = 'Tailscale'

  checksum       = 'c866235f37c6e1501d0da98a09baa300889c1590ac0200e736733c788d054016'
  checksumType   = 'sha256'

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

Install-ChocolateyPackage @packageArgs
# 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"

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
Tailscale 1.54.0 3198 Wednesday, November 15, 2023 Approved
Tailscale 1.52.1 3773 Thursday, November 2, 2023 Approved
Tailscale 1.50.0 8378 Monday, September 25, 2023 Approved
Tailscale 1.48.2 4384 Tuesday, September 12, 2023 Approved
Tailscale 1.48.1 5743 Monday, August 21, 2023 Approved
Tailscale 1.48.0 2009 Wednesday, August 16, 2023 Approved
Tailscale 1.46.1 5053 Wednesday, July 26, 2023 Approved
Tailscale 1.46.0 3423 Wednesday, July 19, 2023 Approved
Tailscale 1.44.2 1026 Tuesday, July 18, 2023 Approved
Tailscale 1.44.0 3909 Wednesday, June 21, 2023 Approved
Tailscale 1.42.0 5159 Wednesday, May 24, 2023 Approved
Tailscale 1.40.1 2878 Thursday, May 11, 2023 Approved
Tailscale 1.40.0 2514 Thursday, April 27, 2023 Approved
Tailscale 1.38.4 3069 Wednesday, April 5, 2023 Approved
Tailscale 1.38.3 1448 Thursday, March 30, 2023 Approved
Tailscale 1.38.1 1994 Friday, March 17, 2023 Approved
Tailscale 1.36.2 2542 Sunday, February 26, 2023 Approved
Tailscale 1.36.0 4595 Wednesday, January 25, 2023 Approved
Tailscale 1.34.2 1691 Monday, January 16, 2023 Approved
Tailscale 1.34.1 2742 Wednesday, December 14, 2022 Approved
Tailscale 1.34.0 1007 Saturday, December 10, 2022 Approved
Tailscale 1.32.3 2287 Monday, November 21, 2022 Approved
Tailscale 1.32.2 1212 Sunday, November 6, 2022 Approved
Tailscale 1.32.1 1103 Monday, October 24, 2022 Approved
Tailscale 1.30.2 1862 Friday, September 16, 2022 Approved
Tailscale 1.30.1 862 Friday, September 9, 2022 Approved
Tailscale 1.28.0 2196 Tuesday, July 19, 2022 Approved
Tailscale 1.26.0 1658 Tuesday, June 7, 2022 Approved
Tailscale 1.24.1 1159 Thursday, April 28, 2022 Approved
Tailscale 1.22.1 1424 Tuesday, March 15, 2022 Approved
Tailscale 1.20.4 832 Saturday, February 19, 2022 Approved
Tailscale 1.20.2 878 Saturday, January 22, 2022 Approved
Tailscale 1.18.2 930 Thursday, December 16, 2021 Approved
Tailscale 1.18.0 859 Friday, November 19, 2021 Approved
Tailscale 1.16.2 592 Saturday, October 30, 2021 Approved
Tailscale 1.16.1 78 Friday, October 29, 2021 Approved
Tailscale 1.16.0 530 Monday, October 11, 2021 Approved
Tailscale 1.14.4 445 Wednesday, September 29, 2021 Approved
Tailscale 1.14.0 571 Tuesday, August 24, 2021 Approved
Tailscale 1.12.3 160 Saturday, August 21, 2021 Approved
Tailscale 1.12.1 543 Wednesday, July 28, 2021 Approved
Tailscale 1.10.2 410 Friday, July 16, 2021 Approved
Tailscale 1.10.1 228 Thursday, July 8, 2021 Approved
Tailscale 1.10.0 367 Sunday, June 27, 2021 Approved
Tailscale 1.8.7 328 Monday, June 14, 2021 Approved
Tailscale 1.8.5 380 Monday, May 24, 2021 Approved
Tailscale 1.8.3 161 Wednesday, May 19, 2021 Approved
Tailscale 1.8.0 163 Thursday, May 6, 2021 Approved
Tailscale 1.6.0 769 Wednesday, March 24, 2021 Approved
Tailscale 1.4.6 170 Monday, March 15, 2021 Approved
Tailscale 1.4.5 206 Wednesday, February 24, 2021 Approved
Tailscale 1.4.4 172 Monday, February 15, 2021 Approved
Tailscale 1.4.0 209 Thursday, January 28, 2021 Approved
Tailscale 1.3.147 218 Tuesday, January 5, 2021 Approved
Tailscale 1.2.9 219 Monday, November 30, 2020 Approved
Tailscale 1.2.5 168 Monday, November 16, 2020 Approved
Tailscale 1.0.4 174 Thursday, October 22, 2020 Approved
Tailscale 1.0.3 305 Tuesday, August 4, 2020 Approved
Tailscale 129 Tuesday, July 28, 2020 Approved
Tailscale 0.99.0 115 Thursday, July 9, 2020 Approved
Tailscale 0.98.0 159 Sunday, June 7, 2020 Approved

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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