Chocolatey Community Coffee Break

Join the Chocolatey Team on our regular monthly stream where we discuss all things Community, what we do, how you can get involved and answer your Chocolatey questions.

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Chocolatey Product Spotlight

Join the Chocolatey Team on our regular monthly stream where we put a spotlight on the most recent Chocolatey product releases. You'll have a chance to have your questions answered in a live Ask Me Anything format.

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Announcing Chocolatey Central Management 0.10.0

Livestream from
Thursday, 06 October 2022

We recently released our largest update to Chocolatey Central Management so far. Join Gary and Steph to find out more about Chocolatey Central Management and the new features and fixes we've added to this release.

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Chocolatey and Intune Overview

Webinar Replay from
Wednesday, 30 March 2022

At Chocolatey Software we strive for simple, and teaching others. Let us teach you just how simple it could be to keep your 3rd party applications updated across your devices, all with Intune!

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Chocolatey For Business. In Azure. In One Click.

Livestream from
Thursday, 9 June 2022

Join James and Josh to show you how you can get the Chocolatey For Business recommended infrastructure and workflow, created, in Azure, in around 20 minutes.

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The Future of Chocolatey CLI

Livestream from
Thursday, 04 August 2022

Join Paul and Gary to hear more about the plans for the Chocolatey CLI in the not so distant future. We'll talk about some cool new features, long term asks from Customers and Community and how you can get involved!

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Hacktoberfest Tuesdays 2022

Livestreams from
October 2022

For Hacktoberfest, Chocolatey ran a livestream every Tuesday! Re-watch Cory, James, Gary, and Rain as they share knowledge on how to contribute to open-source projects such as Chocolatey CLI.

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Chocolatey Product Spotlight: Chocolatey 1.2.0 and Chocolatey Licensed Extension 5.0.0

Livestream from
Thursday, 03 November 2022

Join Paul and Gary for this months Chocolatey product livestream where we look at the latest release of Chocolatey 1.2.0, Chocolatey Licensed Extension 5.0.0 and shine a spotlight on the new hook scripts functionality. This opens up so many possibilities for Chocolatey CLI users!

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Chocolatey Coding Livestream

Livestream from
Tuesday, 29 November 2022

Join Josh as he adds the ability to manage Chocolatey GUI config and features with the Chocolatey Ansible Collection.

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Introduction into Chocolatey with Veeam

Webinar from
Tuesday, 13 December 2022

Join Gary, Paul, and Maurice as they introduce and demonstrate how to use Chocolatey! Questions will be answered live in an Ask Me Anything format.

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Downloads of v 1.14.0:


Last Update:

24 Aug 2021

Package Maintainer(s):

Software Author(s):

  • Tailscale
  • Inc.


tailscale wireguard vpn


This is not the latest version of Tailscale available.

  • 1
  • 2
  • 3

1.14.0 | Updated: 24 Aug 2021



Downloads of v 1.14.0:


Software Author(s):

  • Tailscale
  • Inc.

Tailscale 1.14.0

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="'1.14.0'" [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="'1.14.0'" 

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: '1.14.0'
    state: present

See docs at

chocolatey_package 'tailscale' do
  action    :install
  source   'INTERNAL REPO URL'
  version  '1.14.0'

See docs at

cChocoPackageInstaller tailscale
    Name     = "tailscale"
    Version  = "1.14.0"
    Source   = "INTERNAL REPO URL"

Requires cChoco DSC Resource. See docs at

package { 'tailscale':
  ensure   => '1.14.0',
  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 24 Aug 2021.


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       = '96e9c3f1ad381b1dc7ca24dffe70078adcb42c108a0e89ae49d9870c543410ed'
  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 1.48.1 5402 Monday, August 21, 2023 Approved
Tailscale 1.48.0 1994 Wednesday, August 16, 2023 Approved
Tailscale 1.46.1 4813 Wednesday, July 26, 2023 Approved
Tailscale 1.46.0 3304 Wednesday, July 19, 2023 Approved
Tailscale 1.44.2 1011 Tuesday, July 18, 2023 Approved
Tailscale 1.44.0 3775 Wednesday, June 21, 2023 Approved
Tailscale 1.42.0 5137 Wednesday, May 24, 2023 Approved
Tailscale 1.40.1 2871 Thursday, May 11, 2023 Approved
Tailscale 1.40.0 2441 Thursday, April 27, 2023 Approved
Tailscale 1.38.4 3062 Wednesday, April 5, 2023 Approved
Tailscale 1.38.3 1434 Thursday, March 30, 2023 Approved
Tailscale 1.38.1 1985 Friday, March 17, 2023 Approved
Tailscale 1.36.2 2536 Sunday, February 26, 2023 Approved
Tailscale 1.36.0 4583 Wednesday, January 25, 2023 Approved
Tailscale 1.34.2 1683 Monday, January 16, 2023 Approved
Tailscale 1.34.1 2735 Wednesday, December 14, 2022 Approved
Tailscale 1.34.0 999 Saturday, December 10, 2022 Approved
Tailscale 1.32.3 2282 Monday, November 21, 2022 Approved
Tailscale 1.32.2 1206 Sunday, November 6, 2022 Approved
Tailscale 1.32.1 1096 Monday, October 24, 2022 Approved
Tailscale 1.30.2 1852 Friday, September 16, 2022 Approved
Tailscale 1.30.1 854 Friday, September 9, 2022 Approved
Tailscale 1.28.0 2188 Tuesday, July 19, 2022 Approved
Tailscale 1.26.0 1646 Tuesday, June 7, 2022 Approved
Tailscale 1.24.1 1151 Thursday, April 28, 2022 Approved
Tailscale 1.22.1 1412 Tuesday, March 15, 2022 Approved
Tailscale 1.20.4 825 Saturday, February 19, 2022 Approved
Tailscale 1.20.2 869 Saturday, January 22, 2022 Approved
Tailscale 1.18.2 921 Thursday, December 16, 2021 Approved
Tailscale 1.18.0 846 Friday, November 19, 2021 Approved
Tailscale 1.16.2 581 Saturday, October 30, 2021 Approved
Tailscale 1.16.1 66 Friday, October 29, 2021 Approved
Tailscale 1.16.0 524 Monday, October 11, 2021 Approved
Tailscale 1.14.4 440 Wednesday, September 29, 2021 Approved
Tailscale 1.14.0 563 Tuesday, August 24, 2021 Approved
Tailscale 1.12.3 153 Saturday, August 21, 2021 Approved
Tailscale 1.12.1 536 Wednesday, July 28, 2021 Approved
Tailscale 1.10.2 396 Friday, July 16, 2021 Approved
Tailscale 1.10.1 221 Thursday, July 8, 2021 Approved
Tailscale 1.10.0 360 Sunday, June 27, 2021 Approved
Tailscale 1.8.7 324 Monday, June 14, 2021 Approved
Tailscale 1.8.5 367 Monday, May 24, 2021 Approved
Tailscale 1.8.3 152 Wednesday, May 19, 2021 Approved
Tailscale 1.8.0 157 Thursday, May 6, 2021 Approved
Tailscale 1.6.0 757 Wednesday, March 24, 2021 Approved
Tailscale 1.4.6 163 Monday, March 15, 2021 Approved
Tailscale 1.4.5 200 Wednesday, February 24, 2021 Approved
Tailscale 1.4.4 155 Monday, February 15, 2021 Approved
Tailscale 1.4.0 200 Thursday, January 28, 2021 Approved
Tailscale 1.3.147 213 Tuesday, January 5, 2021 Approved
Tailscale 1.2.9 212 Monday, November 30, 2020 Approved
Tailscale 1.2.5 159 Monday, November 16, 2020 Approved
Tailscale 1.0.4 165 Thursday, October 22, 2020 Approved
Tailscale 1.0.3 288 Tuesday, August 4, 2020 Approved
Tailscale 119 Tuesday, July 28, 2020 Approved
Tailscale 0.99.0 106 Thursday, July 9, 2020 Approved
Tailscale 0.98.0 147 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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