I was able to get Ruby 2.5.1 building on M1 by following two of the steps in that GH issue... https://github.com/rbenv/ruby-build/issues/1691#issuecomment-756272951 https://github.com/rbenv/ruby-build/issues/1691#issuecomment-772224551 I installed `readline` and `openssl` with standard `brew install`. ```bash brew install readline brew install openssl ``` Then I set this in my `~/.zshrc`.. ``` # Homebrew export PATH=/opt/homebrew/bin:$PATH export PATH="/opt/homebrew/sbin:$PATH" # rbenv export RBENV_ROOT=/opt/homebrew/opt/rbenv export PATH=$RBENV_ROOT/bin:$PATH eval "$(rbenv init -)" # openssl export PATH="/opt/homebrew/opt/openssl@1.1/bin:$PATH" export LDFLAGS="-L/opt/homebrew/opt/openssl@1.1/lib" export CPPFLAGS="-I/opt/homebrew/opt/openssl@1.1/include" export PKG_CONFIG_PATH="/opt/homebrew/opt/openssl@1.1/lib/pkgconfig" export RUBY_CONFIGURE_OPTS="--with-openssl-dir=/opt/homebrew/opt/openssl@1.1" ``` Then I ran this command: ``` RUBY_CFLAGS="-Wno-error=implicit-function-declaration" rbenv install 2.5 ``` I haven't been able to test this yet, but @samik3k has reported that this no longer works, but that the following command does. ``` RUBY_CFLAGS=-DUSE_FFI_CLOSURE_ALLOC rbenv install 2.5.8 ``` Please reply and let me know if this works for you and I'll update the steps above as I don't have Ruby setup on my M1 Mac right now.