This guide shows how to set up an old Ruby + Rails environment on a modern macOS (Apple Silicon). As per October 2025, this works on an M1 MacBook Pro (2020) on macOS Sequoia 15.6.1. I assume it will also work on Tahoe 26.0, but I haven't tested it yet.

This is what you’ll end up with:

• Ruby 2.6.10
• OpenSSL 1.1 (needed for Ruby < 3.0)
• MySQL 5.7