The problem seems to be that
homebrew upgraded their openssl install to
1.1. That version of openssl won’t work with rubies prior to
2.4.x. This problem was probably introduced to your Mac when you upgraded homebrew.
/Users/cloudolife/.rvm/rubies/ruby-2.3.0/lib/ruby/site_ruby/2.3.0/rubygems/core_ext/kernel_require.rb:54:in `require': cannot load such file -- openssl (LoadError)
Check the current openssl version.
ls -ls /usr/local/opt/openssl
My work around was to install the older version of openssl (from of all places a tap by rbenv), then reinstall ruby version.
First, Install or downgrade to
ls /usr/local/Cellar/[email protected]/1.0.2t
Then reinstall that ruby version with
[email protected] like this:
Or Upgrade Ruby
Or install ruby 2.4(+) version directly compatible with
 Error while installing Ruby 2.3.7 in mac os 10.15.5 Catalina using RVM; OpenSSL not found - Stack Overflow - https://stackoverflow.com/questions/62288633/error-while-installing-ruby-2-3-7-in-mac-os-10-15-5-catalina-using-rvm-openssl