Table of Contents

  1. Introduction
  2. The Goal
  3. My Environment
  4. Initial Installation
  5. Roadblock
  6. Understanding the Problem
  7. Steps I Tried (That Didn’t Work)
  8. The Breakthrough
  9. The Fix
  10. Key Takeaways
  11. When You Still Need OpenSSL 1.1
  12. Final Thoughts

Introduction

Setting up Ruby with RVM on modern macOS feels deceptively simple until it isn’t. I ran into an issue involving OpenSSL while trying to install the latest Ruby. This post documents the problem, failed attempts, and the eventual fix. I hope this saves you a few hours of debugging.

The Goal

  • Install the latest version of RVM
  • Install the latest Ruby (3.4.x at the time of writing)

My Environment

$ brew config
HOMEBREW_VERSION: 5.1.5
Branch: stable
HOMEBREW_EDITOR: emacsclient
HOMEBREW_PREFIX: /opt/homebrew
macOS: # macOS Tahoe
Rosetta 2: false

Initial Installation

Following the official RVM Installation Guide

# Import GPG keys
$ curl -sSL https://rvm.io/mpapis.asc | gpg --import -
$ curl -sSL https://rvm.io/pkuczynski.asc | gpg --import -

# Install RVM + latest Ruby
$ \curl -sSL https://get.rvm.io | bash -s stable --ruby

Roadblock

The installation failed with an unexpected dependency on openssl@1.1:

$ brew install automake libtool pkg-config coreutils zlib openssl@1.1 --force

Warning: No available formula with the name "openssl@1.1".
Did you mean openssl@3?

Understanding the Problem

How RVM Works

  • Checks for precompiled Ruby binaries:

    $ rvm list known
  • Falls back to compiling from source if needed
  • Installs dependencies via Homebrew

Ruby ↔ OpenSSL Compatibility

Ruby Version OpenSSL Dependency
< 3.0 openssl@1.0
>= 3.1 Works with openssl@3.x

Steps I Tried (That Didn’t Work)

Install latest OpenSSL

$ brew install openssl

Explicit OpenSSL path

$ rvm install 3.4.9 --with-openssl-dir=$(brew --prefix openssl)

Configure PKG CONFIG PATH

$ brew install pkg-config
$ export PKG_CONFIG_PATH="$(brew --prefix openssl)/lib/pkgconfig"
$ rvm install 3.4.9 --with-openssl-dir=$(brew --prefix openssl)

Try reinstalling RVM

$ rm -rf ~/.rvm

$ \curl -sSL https://get.rvm.io | bash -s stable --ruby
rvm install 3.4.9

Cleanup Environment Variables

  • Removed stale PATH
  • Cleaned PKG_CONFIG_PATH
  • Cleaned LD_LIBRARY_PATH

None of these approaches resolved the issue.

The Breakthrough

requirements_osx_brew_libs_install ... openssl@1.1

Root Cause

  • RVM autolibs tries to manage dependencies automatically
  • Misidentifies newer macOS versions
  • Falls back to legacy rules requiring openssl@1.1

The Fix

Disable autolibs and install dependencies manually

$ rvm autolibs disable

$ brew install automake libtool pkg-config coreutils zlib openssl

$ rvm install 3.4.9 --with-openssl-dir=$(brew --prefix openssl)

This resolves the issue successfully.

Key Takeaways

  • Debugging with LLM is fun. They are highly useful for exploration but still requires manual validation
  • The devil is in the details. Good log messages are still the fastest path to the root cause
  • Timeboxing debugging sessions helps avoid fatigue
  • RVM autolibs can misbehave on newer macOS versions
  • Ruby >= 3.1 works well with OpenSSL 3

When You Still Need OpenSSL 1.1

  • Legacy Ruby versions (< 3.0)
  • Older applications with strict dependencies

These setups require manual installation and linking of older OpenSSL versions.

Final Thoughts

This was a great reminder:

The problem is rarely where you first look.

Understanding and questioning system assumptions is often more valuable than repeatedly retrying commands.