Workaround to install Ruby 2.x on macOS 11.6 Big Sur with MacPorts

I recently invested a significant amount of time trying to install Ruby 2.x on a new Mac using MacPorts. Apparently, the problem was that RVM was trying to build against the latest version of OpenSSL (v3) which Ruby 2.x is not compatible with.

The solution I found was:

1. Install MacPorts
2. Install RVM
3. rvm --autolibs=macports requirements $RUBY_VERSION to install all requirements including the wrong openssl package.
4. sudo port uninstall openssl openssl3 to remove OpenSSL 3; to prevent the 3.x headers from being picked up during the install process.
5. sudo port install openssl11 to install OpenSSL 1.1

Then, I could install any Ruby from 2.4 to 2.7 like so:

export LDFLAGS="-L/opt/local/libexec/openssl11/lib -L/opt/local/lib"
export CPPFLAGS="-I/opt/local/libexec/openssl11/include -I/opt/local/include"
~/.rvm/bin/rvm --autolibs=disable install $RUBY_VERSION

Afterward, the openssl3 package can be reinstalled or reactivated and the RVM-installed Rubies will continue to work.

I have successfully used these steps on both an x86_64 and arm64 Mac.

Environment info

system:

  system:
    uname:        "Darwin BRagheb-MBP16-BEI.local 20.6.0 Darwin Kernel Version 20.6.0: Wed Nov 10 22:23:07 PST 2021; root:xnu-7195.141.14~1/RELEASE_X86_64 x86_64"
    name:         "OSX"
    version:      "11.6"
    architecture: "x86_64"
    bash:         "/bin/bash => GNU bash, version 3.2.57(1)-release (x86_64-apple-darwin20)"
    zsh:          "/bin/zsh => zsh 5.8 (x86_64-apple-darwin20.0)"
    remote_path:  "osx/11.6/x86_64"
    xcode:        "13.2.1"

  rvm:
    version:      "1.29.12 (latest)"
    updated:      "11 days 11 minutes 15 seconds ago"
    path:         "/Users/benragheb/.rvm"
    autolibs:     "[read-fail] Allow RVM to use package manager if found, fail if dependencies are missing. This is default."

  homes:
    gem:          "not set"
    ruby:         "not set"

  binaries:
    ruby:         "/usr/bin/ruby"
    irb:          "/usr/bin/irb"
    gem:          "/usr/bin/gem"
    rake:         "/usr/bin/rake"

  environment:
    PATH:         "/Users/benragheb/.nvm/versions/node/v12.12.0/bin:/opt/local/bin:/opt/local/sbin:/usr/local/bin:/usr/bin:/bin:/usr/sbin:/sbin:/Library/Apple/usr/bin:/Users/benragheb/.rvm/bin"
    GEM_HOME:     ""
    GEM_PATH:     ""
    MY_RUBY_HOME: ""
    IRBRC:        ""
    RUBYOPT:      ""
    gemset:       ""