Ruby 3.4.3 fails install on Mac Sequoia due to obsolete openssl requirement

[ak47]

I don't understand what is happening. From what I've read current versions of Ruby do not need openssl 1.1, yet rbenv is failing to install latest stable Ruby 3.4.3 as it tries to use [email protected] - which I don't have installed and don't understand why rbenv is insisting on using this version. The remediations suggested also don't make sense as they all reflect a need for openssl 1.1.

Am I doing something wrong here? have I got a misconfiguration somewhere?

oh the frustration...

(mlops) (base) ➜  mlops-course-sds git:(master) rbenv install 3.4.3 -f
==> Downloading ruby-3.4.3.tar.gz...
-> curl -q -fL -o ruby-3.4.3.tar.gz https://cache.ruby-lang.org/pub/ruby/3.4/ruby-3.4.3.tar.gz
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 22.1M  100 22.1M    0     0   9.8M      0  0:00:02  0:00:02 --:--:--  9.8M
==> Installing ruby-3.4.3...
ruby-build: using gmp from homebrew
-> ./configure "--prefix=$HOME/.rbenv/versions/3.4.3" --enable-shared --with-gmp-dir=/opt/homebrew/opt/gmp --with-ext=openssl,psych,+ --with-zlib-dir=/opt/homebrew/opt/zlib --with-openssl-dir=/opt/homebrew/opt/[email protected] --with-readline-dir=/opt/homebrew/opt/readline --with-libyaml-dir=/opt/homebrew/opt/libyaml --with-gdbm-dir=/opt/homebrew/opt/gdbm
-> make -j 8
*** Following extensions are not compiled:
openssl:
	Could not be configured. It will not be installed.
	/private/var/folders/3n/b2mmk_7s0d33_fp1kkzcnf480000gn/T/ruby-build.20250513151930.3473.avRj6A/ruby-3.4.3/ext/openssl/extconf.rb:26: OpenSSL library directory could not be found in '/opt/homebrew/opt/[email protected]/lib'. You might want to fix this error in one of the following ways.
	  * Recompile OpenSSL by configuring it with --libdir=lib  to specify the OpenSSL library directory.
	  * Recompile Ruby by configuring it with --libdir=<dir> to specify the Ruby library directory.
	  * Compile this openssl gem with --with-openssl-include=<dir> and --with-openssl-lib=<dir> options to specify the OpenSSL include and library directories.
	Check /var/folders/3n/b2mmk_7s0d33_fp1kkzcnf480000gn/T/ruby-build.20250513151930.3473.avRj6A/ruby-3.4.3/ext/openssl/mkmf.log for more details.

BUILD FAILED (macOS 15.4.1 on arm64 using ruby-build 20250507)

[ak47]

I found the issue, I had a misconfiguration from long ago in my .zshrc

export RUBY_CONFIGURE_OPTS="--with-zlib-dir=$(brew --prefix zlib) --with-openssl-dir=$(brew --prefix [email protected]) --with-readline-dir=$(brew --prefix readline) --with-libyaml-dir=$(brew --prefix libyaml) --with-gdbm-dir=$(brew --prefix gdbm)"

deleted that, and replaced with:
export RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@3)"