How to Install Older Versions of Ruby
The problem is with RVM and renv and not with asdf, so my first suggestion is to change to asdf if you keep with RVM: install older versions of ruby <2.3 with support for openssl 1.0x you can follow these instructions: # before you install command line tools and gcc xcode-select --install brew install gcc # installation procedure cd /usr/local/src curl -O https://www.openssl.org/source/openssl-1.0.2t.tar.gz tar xzf openssl-1.0.2t.tar.gz cd openssl-1.0.2t ./Configure darwin64-x86_64-cc make sudo make install export LDFLAGS=“-L/usr/local/ssl/lib” export CPPFLAGS=“-I/usr/local/ssl/include” export PKG_CONFIG_PATH=“/usr/local/ssl/lib/pkgconfig” rvm reinstall 2.3.8 --with-openssl-dir=/usr/local/ssl --with-openssl-include=/usr/local/ssl/include