I recommend using Chocolatey to manage your ruby installation.

It's a unix style package manager for windows.

It's quite easy to install, you can find instructions on their website.

In cmd.exe (run as administrator):

@powershell -NoProfile -ExecutionPolicy Bypass -Command "iex ((new-object net.webclient).DownloadString('https://chocolatey.org/install.ps1'))" && SET PATH=%PATH%;%ALLUSERSPROFILE%\chocolatey\bin

Then you can install ruby:

choco install ruby

And upgrade it later:

choco upgrade ruby
Answer from sokkyoku on Stack Overflow
🌐
Ruby
ruby-lang.org › en › documentation › installation
Installing Ruby | Ruby
However, the third-party tools might be a good way to obtain the latest version of Ruby. On Windows, you can use the Windows Package Manager CLI to install Ruby:
Discussions

Why, When, and How to Upgrade the Ruby Version in Your Project
All the time, every time. Much easier to stay in the flow and upgrade gradually than try to make a big jump. More on reddit.com
🌐 r/ruby
4
21
January 25, 2023
How do you install old ruby versions?
I had this issue a while ago... All I can say is if it's ruby <=2.3 is good luck..... And sorry .. Try to dockerize, or if possible upgrade ruby to a more up to date version. More on reddit.com
🌐 r/ruby
16
2
February 7, 2026
Help Upgrade Ruby version from 2.3.8
You might want to consider a service like https://www.fastruby.io/ or https://railslts.com/ - fixing build problems with ancient versions is no fun if you’re starting from scratch. More on reddit.com
🌐 r/ruby
15
3
May 23, 2025
How can I downgrade to ruby 2.7.0 on a Mac?

I use rbenv which is not quite as invasive as rvm. I can have multiple versions installed and do things like:

rbenv install 3.0.0 # Need to also have ruby-build installed.

rbenv global 2.7.0 # This version will be used when not overridden by the next command.

rbenv local 2.7.3 # Will use this only in current directory.

More on reddit.com
🌐 r/ruby
19
4
April 30, 2021
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RubyInstaller
rubyinstaller.org
RubyInstaller for Windows
The easy way to install Ruby on Windows This is a self-contained Windows-based installer that includes the Ruby language, an execution environment, important...
🌐
Medium
ancarrillo964.medium.com › get-or-update-ruby-on-your-computer-dcf383221ef1
Get or update Ruby on your computer | by Anthony N. Carrillo | Medium
June 23, 2020 - I actually started with the Ruby coding language and it was interesting. It can do a ton very simply and is best at web development. Web-Dev is still very popular even though there are sites where you can construct your own, its best in my opinion to build your own. But ultimately it is up to you. I found it interesting and I hope you do as well. ... On Windows, RubyInstaller appears to be the most popular.
🌐
Hibbard
hibbard.eu › how-to-manage-multiple-versions-of-ruby-on-windows
How to Manage Multiple Versions of Ruby on Windows · James Hibbard
pik bills itself as a tool to manage multiple versions of Ruby on Windows which can be used from the Windows command line (cmd.exe), Windows PowerShell, or Git Bash.
🌐
FastRuby
fastruby.io › blog › step-by-step-ruby-upgrade.html
A Step-by-Step Guide to Upgrading Your Ruby Version - FastRuby.io | Rails Upgrade Service
March 13, 2025 - Review the current Ruby version and decide on a targeted version. We suggest doing gradual, incremental upgrades, aiming to only upgrade to the next stable version at a time. This approach helps avoid significant changes that may pose challenges and unnecessary complexity. You can find a list of all releases here opens a new window to determine what the next stable version for your application should be.
🌐
Ruby on Rails
guides.rubyonrails.org › upgrading_ruby_on_rails.html
Upgrading Ruby on Rails — Ruby on Rails Guides
It's a good idea to upgrade Ruby and Rails separately. Upgrade to the latest Ruby you can first, and then upgrade Rails. When changing Rails versions, it's best to move slowly, one minor version at a time, in order to make good use of the deprecation warnings.
Find elsewhere
🌐
Reddit
reddit.com › r/ruby › why, when, and how to upgrade the ruby version in your project
r/ruby on Reddit: Why, When, and How to Upgrade the Ruby Version in Your Project
January 25, 2023 - After seeing many people struggle to install older Ruby versions, I wrote this detailed guide that explains the why, when, and how to update the Ruby version in your project (Rails, Jekyll, Sinatra, ReactNative, etc.).
🌐
GoRails
gorails.com › episodes › how-to-upgrade-ruby-versions
How to Upgrade Ruby Versions | GoRails
Over time, you'll need to upgrade the Ruby version of your Rails application. For example, a new version of Ruby was released since we started this series that fixes a couple security issues in Ruby so we'll teach you how to upgrade your Ruby version.
Published   April 5, 2023
🌐
RubyInstaller
rubyinstaller.org › downloads
Downloads
It provides the biggest number of compatible gems and installs the MSYS2 Devkit alongside Ruby, so gems with C-extensions can be compiled immediately. The 32 bit (x86) version is not recommended, unless custom 32 bit native DLLs or COM objects have to be used. Ruby can be updated to the latest patch version (e.g.
🌐
GitHub
collectionbuilder.github.io › cb-docs › docs › software › ruby_windows
Windows - Ruby Install | CollectionBuilder Documentation
To update, type the command: gem update --system ... The Ruby MSYS2 DevKit installer can be restarted if necessary by typing ridk install into a command prompt. Ruby 3.2.0 was not working with some Jekyll versions–if you have 3.2.0, please update your Ruby and Jekyll to avoid issues!
🌐
Reddit
reddit.com › r/ruby › how do you install old ruby versions?
r/ruby on Reddit: How do you install old ruby versions?
February 7, 2026 -

I used to Linux mint and mise as ruby version manager. Most of the time I work with old project with ruby version 2.6.3, 2.7.8 and so on.
I've tried CachyOS Hyprland recently and want to make it as main system. And I failed to install old ruby versions, it's always some error with old gcc or old openssl and old whatever.

I can't simply dockerize application or upgrade ruby version on project, I am pretty used to have ruby system-wide installed. Is there any way to install old ruby version without pain?

🌐
Medium
medium.com › @redswitches › install-ruby-on-windows-10-fd1f62e3231e
Install Ruby on Windows 10 | Medium
July 18, 2024 - ... Download the latest RubyInstaller from the official website and run the installer. You may also need to update gems using gem update — system and individual gems with gem update.
Top answer
1 of 4
50

There are two major Ruby version managers out there from which you can choose:

  • rbenv and ruby-build
  • RVM

These allow you to keep multiple versions of Ruby on the same system. Once you've installed a version manager, and installed your own Ruby version, you won't mess with your system's Ruby and its Gems, which is the greatest benefit. No more sudo! No more permissions errors and Gem conflicts.

Which one should I choose?

Both do the same thing, but they follow different philosophies. The choice is up to you.

I personally recommend rbenv for its simplicity. I've been using it for years and it has always worked well.

How do I install them?

If you choose rbenv:

  • Follow the all the installation and setup instructions.
  • Install ruby-build
  • Run rbenv install x.x.x where x.x.x is the version (use rbenv install --list to see which ones are available
  • Run rbenv global x.x.x to change your global Ruby version

If you choose RVM:

  • Use the secure installation method
  • Read the installation instructions — you probably want the single-user configuration
  • Use rvm list known to list available Rubies and then run rvm install x.x.x to install a specific version.
  • Use rvm use x.x.x --default to change your default Ruby
2 of 4
9

I think rbenv deserves at least its own answer.

There is a constant battle between fans of rbenv and those of RVM but I personally like rbenv a lot more. As the Sam Stephenson (the author) states, rbenv it solely concerned with switching Ruby versions (as opposed to RVM, which does a lot more).

On OS X, it's especially easy to give it a try. Just follow the excellent installation instructions on the Github page (if you have Homebrew installed, it's basically just a brew install rbenv ruby-build).

As for switching Rails versions, I once wrote an article about that which my be of interest for you.

🌐
Aleteia
reports-doc.aleteia.org › ruby upgrade guide
Ruby Upgrade Guide | Aleteia Reports
# Install Ruby 3.4.0 (using your version manager) rbenv install 3.4.0 # or rvm install 3.4.0 # Install dependencies bundle install # Run tests bundle exec rspec # Run linters bundle exec rubocop
🌐
React Native
reactnative.dev › docs › set-up-your-environment
Set Up Your Environment · React Native
3 weeks ago - If you want to be able to switch between different versions, you might want to install Node via nvm-windows, a Node version manager for Windows.
🌐
Plesk
docs.plesk.com › release-notes › obsidian › change-log
Change Log for Plesk Obsidian
Updated .NET to versions 10.0.4, 9.0.14, and 8.0.25. Updated Git for Windows to version 2.53.0.2.
🌐
Reddit
reddit.com › r/ruby › help upgrade ruby version from 2.3.8
r/ruby on Reddit: Help Upgrade Ruby version from 2.3.8
May 23, 2025 -

Hello, I hope you're all doing great.

We have an old project at working using ruby:2.3.8 and rails 4.0.5 this week the docker image didn't build because of some expired packages on Debian this step fail 'RUN echo "deb http://archive.debian.org/debian stretch main contrib non-free" > /etc/apt/sources.list" it's a big project now I have to upgrade it to solve the build project I don't have any experience with Ruby what is the best approach to follow.

Thanks for the help

🌐
Oracle
oracle.com › database › technologies › oracle-database-software-downloads.html
Database Software Downloads
Download the latest Database Software 26ai or all previous versions Windows, Linux Oracle Solaris, IBM AIX, HP-UX and more.
🌐
Mac Install Guide
mac.install.guide › ruby
Install the Latest Ruby Version · Ruby 4.0 · Mac Install Guide
If you've already installed an earlier version of Ruby: ... The guide gives you instructions for updates with all popular installation methods.