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

Webinar from
Wednesday, 17 January 2024

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

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Chocolatey and Intune Overview

Webinar Replay from
Wednesday, 30 March 2022

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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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Downloads of v 3.2.1:


Last Update:

31 Jan 2024

Package Maintainer(s):

Software Author(s):

  • OpenSSL Team.




  • 1
  • 2
  • 3

3.2.1 | Updated: 31 Jan 2024



Downloads of v 3.2.1:


Software Author(s):

  • OpenSSL Team.



OpenSSL 3.2.1

  • 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 OpenSSL, run the following command from the command line or from PowerShell:


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


To uninstall OpenSSL, 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 openssl -y --source="'INTERNAL REPO URL'" [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 openssl -y --source="'INTERNAL REPO URL'" 

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

Exit $exitCode

- name: Install openssl
    name: openssl
    version: '3.2.1'
    state: present

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

chocolatey_package 'openssl' do
  action    :install
  source   'INTERNAL REPO URL'
  version  '3.2.1'

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

cChocoPackageInstaller openssl
    Name     = "openssl"
    Version  = "3.2.1"
    Source   = "INTERNAL REPO URL"

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

package { 'openssl':
  ensure   => '3.2.1',
  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 31 Jan 2024.


The Win32/Win64 OpenSSL Installation Project is dedicated to providing a simple installation of OpenSSL for Microsoft Windows. It is easy to set up and easy to use through the simple, effective installer. No need to compile anything or jump through any hoops, just click a few times and it is installed, leaving you to doing real work. Download it today! Note that these are default builds of OpenSSL and subject to local and state laws. More information can be found in the legal agreement of the installation.

LEGAL NOTICE: This product includes software developed by the OpenSSL Project for use in the OpenSSL Toolkit. (http://www.openssl.org/)

$ErrorActionPreference = 'Stop';

$packageArgs = @{
  packageName     = $env:ChocolateyPackageName
  url32           = 'https://slproweb.com/download/Win32OpenSSL-3_2_1.exe'  
  checksumType32  = 'sha512'
  checksum32      = 'a267bf8f220f334ba86b46f30ccd2e7aa73519b904612b56b3fc7f69fed04e2e2b8902fdbbb9d9d7cbf10fe5687b530e3e3d1d71f8b4027e2084616bdacb4383'

  url64           = 'https://slproweb.com/download/Win64OpenSSL-3_2_1.exe'
  checksumType64  = 'sha512'
  checksum64      = '657f7cb56d8ae48b60812ce1d42c5158c953b438a9ea013b98dd6cbeca3a51b919636a68a9801af07410af50e90fbbdc20d1ce783e4e65356d61002a15b606cc'

Install-ChocolateyPackage @packageArgs

$path = Get-AppInstallLocation OpenSSL-Win
Install-ChocolateyPath -PathToInstall "$path\bin"
Install-ChocolateyEnvironmentVariable -VariableName OPENSSL_CONF -VariableValue "$path\bin\openssl.cfg"

Write-Warning "OPENSSL_CONF has been set to $path\bin\openssl.cfg"
$ErrorActionPreference = 'Stop'
Uninstall-ChocolateyEnvironmentVariable -VariableName OPENSSL_CONF

$path = Get-AppInstallLocation OpenSSL-Win
$pathToRemove = "$path\bin\"
foreach ($registryPath in 'hklm:\system\currentcontrolset\control\session manager\environment', 'hkcu:\environment') {
  $p = (Get-Itemproperty -path "$registryPath" -Name Path).Path
  if ("$p" | Select-String -SimpleMatch "$pathToRemove"){
    $newPath = ("$p" -split ';' | ForEach-Object { if (-not ($_ -eq "$pathToRemove")) { $_ } } ) -join ';'
    Set-ItemProperty -path "$registryPath" -Name Path -Value $NewPath

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
OpenSSL 3.2.0 34954 Sunday, January 14, 2024 Approved
OpenSSL 3.1.1 432472 Tuesday, July 18, 2023 Approved
OpenSSL 110516 Wednesday, May 31, 2023 Approved
OpenSSL 171618 Thursday, February 9, 2023 Approved
OpenSSL 138867 Wednesday, November 2, 2022 Approved
OpenSSL 162020 Wednesday, July 6, 2022 Approved
OpenSSL 20936 Wednesday, June 22, 2022 Approved
OpenSSL 53917 Wednesday, May 4, 2022 Approved
OpenSSL 50335 Wednesday, March 16, 2022 Approved
OpenSSL 76520 Thursday, December 16, 2021 Approved
OpenSSL 33330 Thursday, November 11, 2021 Approved
OpenSSL 171187 Friday, March 26, 2021 Approved
OpenSSL 28054 Thursday, February 18, 2021 Approved
OpenSSL 57582 Wednesday, December 9, 2020 Approved
OpenSSL 58882 Wednesday, September 23, 2020 Approved
OpenSSL 73623 Tuesday, April 21, 2020 Approved
OpenSSL 6004 Wednesday, April 1, 2020 Approved
OpenSSL 16497 Thursday, March 19, 2020 Approved
OpenSSL 15503 Saturday, January 11, 2020 Approved
OpenSSL 18058 Thursday, September 12, 2019 Approved
OpenSSL 1495 Tuesday, September 10, 2019 Approved

Discussion for the OpenSSL Package

Ground Rules:

  • This discussion is only about OpenSSL and the OpenSSL 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 OpenSSL, 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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