Install OpenSSL 1.0.2 via Homebrew ( Fix for older Ruby Versions )

OpenSSL-Fix.md

How to fix openSSL incompatibility issues in older Ruby Versions. (<=2.3)

Homebrew

Install openssl 1.0.2 via homebrew :

brew install https://raw.githubusercontent.com/Homebrew/homebrew-core/64555220bfbf4a25598523c2e4d3a232560eaad7/Formula/openssl.rb -f

This should install openssl in /usr/local/opt/openssl

If you already have 1.1 installed, you should have 2 versions of opensll in: /user/local/opt/

• [email protected]
• openssl (1.0)

RVM

Install or Reinstall the version you want, but you must do it with --with-openssl-dir and pass the path of openssl (1.0).
In my case is /usr/local/opt/openssl

rvm install YOUR-RUBY-VERSION  --with-openssl-dir='/usr/local/opt/openssl'

For ubuntu 20.04, follow these steps to install openssl 1.0:

• Edit /etc/apt/sources.list and add this at the end of the file: deb http://security.ubuntu.com/ubuntu bionic-security main
• Run sudo apt-get update && apt-cache policy libssl1.0-dev
• Run sudo apt-get install libssl1.0-dev

Then run the RVM command with your openssl1.0 dir (/usr/local/ssl/bin here, you can check if the version is correct with ./usr/local/ssl/bin/openssl version):
rvm install YOUR-RUBY-VERSION --with-openssl-dir='/usr/local/ssl/bin'

For ubuntu 20.04, follow these steps to install openssl 1.0:

• Edit /etc/apt/sources.list and add this at the end of the file: deb http://security.ubuntu.com/ubuntu bionic-security main
• Run sudo apt-get update && apt-cache policy libssl1.0-dev
• Run sudo apt-get install libssl1.0-dev

Then run the RVM command with your openssl1.0 dir (/usr/local/ssl/bin here, you can check if the version is correct with ./usr/local/ssl/bin/openssl version):
rvm install YOUR-RUBY-VERSION --with-openssl-dir='/usr/local/ssl/bin'

Also for asdf:

After installing libssl1.0

PKG_CONFIG_PATH=/usr/lib/openssl-1.0/pkgconfig \
RUBY_EXTRA_CONFIGURE_OPTIONS="--with-openssl-dir=/usr/lib/openssl-1.0" \
asdf install YOUR-RUBY-VERSION

For rbenv

RUBY_CONFIGURE_OPTS=--with-openssl-dir=/home/linuxbrew/.linuxbrew/Cellar/[email protected]/1.1.1o/ rbenv install

For Ubuntu 22.04 LTS on WSL none of those worked for me. Somehow it will add openssl 3.0 to my ruby installs.
Fortunately this did the trick:

rvm pkg install openssl
rvm remove your-ruby-version
rvm install 2.7.2 --with-openssl-dir=$HOME/.rvm/usr

The first line will install openssl 1.0.1i on your .rvm folder (yes didn't expect that. That's the magic trick)
I add the 'rvm remove' because I previously installed ruby. So I preferred a clean install.
Install your desired version and it will be linked correctly to the openssl 1.0.1i folder.
Now confirm the openssl version Ruby has:
ruby -ropenssl -e 'puts OpenSSL::OPENSSL_LIBRARY_VERSION'