Issue #19794 has been updated by monfresh (Moncef Belyamani). I think something else is going on here. On a fresh macOS installation, the `/usr/local` directory has been completely empty for several macOS versions now, since at least Catalina, and most likely earlier versions as well. I know this because I specialize in Ruby installation on Mac. I'm the creator of "Ruby on Mac" (rubyonmac.dev). I just installed Ruby 3.2.2 on macOS Sonoma 14.0 (release candidate) without any issues using my Ruby on Mac product. I also tried it directly with `rbenv` and it worked. This is on an M1 Mini with nothing in `/usr/local` and with Homebrew installed in `/opt/homebrew` If every version manager and installing from source failed, then perhaps there was a bug in Sonoma beta 4, or an incompatibility with Homebrew, or something wrong, outdated, misconfigured, or missing in @jhaungs dev setup on their Mac. If they're on an Intel Mac and `/usr/local` was empty, that would indicate that Homebrew wasn't installed yet. Another possible reason for this failure is that `/usr/local/lib` is a symlink to some file. This might sound farfetched, but I had a customer who had done just that. In my experience helping thousands of people over the past 12 years, the vast majority of installation issues are due to missing prerequisites, outdated or misconfigured tools, and setting incorrect or unnecessary Ruby compilation flags, either globally in the shell startup file or in the terminal as part of the installation command. ---------------------------------------- Bug #19794: Ruby 3.2.2 fails to build on macOS Sonoma betas https://bugs.ruby-lang.org/issues/19794#change-104693 * Author: jhaungs (Jim Haungs) * Status: Assigned * Priority: Normal * Assignee: nobu (Nobuyoshi Nakada) * ruby -v: 3.2.2 * Backport: 3.0: UNKNOWN, 3.1: UNKNOWN, 3.2: UNKNOWN ---------------------------------------- With Big Sur, Apple deprecated putting dylibs in /usr/local/lib. In Sonoma (beta 4), this directory has disappeared completely. However, ruby's configure script depends on its existence. So, virtually every ruby installer (RVM, rbenv, asdf, ruby-build, and even building from source tarball) fails. When building ruby 3.2.2 from source, the configure step outputs the irritatingly useless "something wrong with LDFLAGS" error message and fails to build. The solution was to `cd /usr/local; sudo mkdir lib` to create the missing lib directory under /usr/local. It would be nice to remove this dependency from the configure script. -- https://bugs.ruby-lang.org/