Unpacking Software Livestream

Join our monthly Unpacking Software livestream to hear about the latest news, chat and opinion on packaging, software deployment and lifecycle management!

Learn More

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.

Learn More

Chocolatey Coding Livestream

Join us for the Chocolatey Coding Livestream, where members of our team dive into the heart of open source development by coding live on various Chocolatey projects. Tune in to witness real-time coding, ask questions, and gain insights into the world of package management. Don't miss this opportunity to engage with our team and contribute to the future of Chocolatey!

Learn More

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

Webinar from
Wednesday, 17 January 2024

We are delighted to announce the release of Chocolatey Central Management v0.12.0, featuring seamless Deployment Plan creation, time-saving duplications, insightful Group Details, an upgraded Dashboard, bug fixes, user interface polishing, and refined documentation. As an added bonus we'll have members of our Solutions Engineering team on-hand to dive into some interesting ways you can leverage the new features available!

Watch On-Demand
Chocolatey Community Coffee Break

Join the Chocolatey Team as we discuss all things Community, what we do, how you can get involved and answer your Chocolatey questions.

Watch The Replays
Chocolatey and Intune Overview

Webinar Replay from
Wednesday, 30 March 2022

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

Watch On-Demand
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.

Watch On-Demand
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!

Watch On-Demand
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.

Watch On-Demand



Downloads of v


Last Update:

28 Jul 2020

Package Maintainer(s):

Software Author(s):

  • Tailscale
  • Inc.


tailscale wireguard vpn


This is not the latest version of Tailscale available.

  • 1
  • 2
  • 3 | Updated: 28 Jul 2020



Downloads of v


Software Author(s):

  • Tailscale
  • Inc.


This is not the latest version of Tailscale available.

  • 1
  • 2
  • 3

Some Checks Have Failed or Are Not Yet Complete

Not All Tests Have Passed

Validation Testing Passed

Verification Testing Passed


Scan Testing Resulted in Flagged:

This package was submitted (and approved) prior to automated virus scanning integration into the package moderation processs.

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

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 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

  • 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

3. Copy Your Script

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

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: ''
    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  ''

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

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

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

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


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 28 Jul 2020.


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.

# 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"
$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-0.100.0-107.exe'

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

  softwareName  = 'Tailscale IPN'

  checksum      = 'cae3f6c4d01d7a0b06de6b688b1417c12a54b4cdef10fd04347e631865371f1b'
  checksumType  = 'sha256'

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

Install-ChocolateyPackage @packageArgs


$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

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 1.58.2 5831 Tuesday, January 23, 2024 Approved
Tailscale 1.58.0 2772 Friday, January 19, 2024 Approved
Tailscale 1.56.1 8624 Friday, December 15, 2023 Approved
Tailscale 1.56.0 1650 Wednesday, December 13, 2023 Approved
Tailscale 1.54.1 4074 Thursday, November 30, 2023 Approved
Tailscale 1.54.0 3392 Wednesday, November 15, 2023 Approved
Tailscale 1.52.1 3848 Thursday, November 2, 2023 Approved
Tailscale 1.50.0 10106 Monday, September 25, 2023 Approved
Tailscale 1.48.2 4432 Tuesday, September 12, 2023 Approved
Tailscale 1.48.1 5750 Monday, August 21, 2023 Approved
Tailscale 1.48.0 2012 Wednesday, August 16, 2023 Approved
Tailscale 1.46.1 5207 Wednesday, July 26, 2023 Approved
Tailscale 1.46.0 3458 Wednesday, July 19, 2023 Approved
Tailscale 1.44.2 1030 Tuesday, July 18, 2023 Approved
Tailscale 1.44.0 4026 Wednesday, June 21, 2023 Approved
Tailscale 1.42.0 5164 Wednesday, May 24, 2023 Approved
Tailscale 1.40.1 2881 Thursday, May 11, 2023 Approved
Tailscale 1.40.0 2607 Thursday, April 27, 2023 Approved
Tailscale 1.38.4 3071 Wednesday, April 5, 2023 Approved
Tailscale 1.38.3 1451 Thursday, March 30, 2023 Approved
Tailscale 1.38.1 1997 Friday, March 17, 2023 Approved
Tailscale 1.36.2 2545 Sunday, February 26, 2023 Approved
Tailscale 1.36.0 4599 Wednesday, January 25, 2023 Approved
Tailscale 1.34.2 1694 Monday, January 16, 2023 Approved
Tailscale 1.34.1 2745 Wednesday, December 14, 2022 Approved
Tailscale 1.34.0 1011 Saturday, December 10, 2022 Approved
Tailscale 1.32.3 2292 Monday, November 21, 2022 Approved
Tailscale 1.32.2 1215 Sunday, November 6, 2022 Approved
Tailscale 1.32.1 1105 Monday, October 24, 2022 Approved
Tailscale 1.30.2 1866 Friday, September 16, 2022 Approved
Tailscale 1.30.1 864 Friday, September 9, 2022 Approved
Tailscale 1.28.0 2198 Tuesday, July 19, 2022 Approved
Tailscale 1.26.0 1662 Tuesday, June 7, 2022 Approved
Tailscale 1.24.1 1161 Thursday, April 28, 2022 Approved
Tailscale 1.22.1 1433 Tuesday, March 15, 2022 Approved
Tailscale 1.20.4 834 Saturday, February 19, 2022 Approved
Tailscale 1.20.2 882 Saturday, January 22, 2022 Approved
Tailscale 1.18.2 933 Thursday, December 16, 2021 Approved
Tailscale 1.18.0 865 Friday, November 19, 2021 Approved
Tailscale 1.16.2 596 Saturday, October 30, 2021 Approved
Tailscale 1.16.1 80 Friday, October 29, 2021 Approved
Tailscale 1.16.0 533 Monday, October 11, 2021 Approved
Tailscale 1.14.4 449 Wednesday, September 29, 2021 Approved
Tailscale 1.14.0 573 Tuesday, August 24, 2021 Approved
Tailscale 1.12.3 163 Saturday, August 21, 2021 Approved
Tailscale 1.12.1 546 Wednesday, July 28, 2021 Approved
Tailscale 1.10.2 413 Friday, July 16, 2021 Approved
Tailscale 1.10.1 231 Thursday, July 8, 2021 Approved
Tailscale 1.10.0 372 Sunday, June 27, 2021 Approved
Tailscale 1.8.7 330 Monday, June 14, 2021 Approved
Tailscale 1.8.5 385 Monday, May 24, 2021 Approved
Tailscale 1.8.3 163 Wednesday, May 19, 2021 Approved
Tailscale 1.8.0 169 Thursday, May 6, 2021 Approved
Tailscale 1.6.0 772 Wednesday, March 24, 2021 Approved
Tailscale 1.4.6 173 Monday, March 15, 2021 Approved
Tailscale 1.4.5 210 Wednesday, February 24, 2021 Approved
Tailscale 1.4.4 175 Monday, February 15, 2021 Approved
Tailscale 1.4.0 213 Thursday, January 28, 2021 Approved
Tailscale 1.3.147 225 Tuesday, January 5, 2021 Approved
Tailscale 1.2.9 224 Monday, November 30, 2020 Approved
Tailscale 1.2.5 171 Monday, November 16, 2020 Approved
Tailscale 1.0.4 179 Thursday, October 22, 2020 Approved
Tailscale 1.0.3 309 Tuesday, August 4, 2020 Approved
Tailscale 135 Tuesday, July 28, 2020 Approved
Tailscale 0.99.0 118 Thursday, July 9, 2020 Approved
Tailscale 0.98.0 164 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.
comments powered by Disqus