Solution: Download OpenSSL 1.1.1 $ cd ~/Downloads $ wget https://www.openssl.org/source/openssl-1.1.1q.tar.gz $ tar xf openssl-1.1.1q.tar.gz Compile it $ cd ~/Downloads/openssl-1.1.1q $ ./config --prefix=/opt/openssl-1.1.1q --openssldir=/opt/openssl-1.1.1q shared zlib $ make $ make test $ sudo make install Link the system's certs to OpenSSL 1.1.1 directory $ sudo rm -rf /opt/openssl-1.1.1q/certs $ sudo ln -s /etc/ssl/certs /opt/openssl-1.1.1q Install ruby $ RUBY_CONFIGURE_OPTS=--with-openssl-dir=/opt/openssl-1.1.1q asdf install ruby 2.7.5 Error: `require': libssl.so.1.1: cannot open shared object file: No such file or directory - /tmp/ruby-build.... References: https://github.com/rbenv/ruby-build/discussions/1940 https://gist.github.com/yob/08d53a003181aa0fcce9812b1b533870 https://blog.chetanmittaldev.com/how-to-install-older-rubies-on-ubuntu-2204-using-rvm https://github.com/rvm/rvm/issues/5209