souzagab/OpenSSL-Fix.md

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

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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/

openssl@1.1
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'

alpacin0 commented Dec 24, 2023

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'