A Tale of OpenSSL and Persistence

Picture this: You’re excited to dive into Ruby on Rails 8 development on your shiny new M1/M2 Mac, but OpenSSL is giving you the cold shoulder. Don’t worry – you’re not alone in this dance! Let’s turn that frustration into a success story with this comprehensive guide.

The Challenge

If you’ve tried installing Ruby 3.4.1 on your Apple Silicon Mac and encountered OpenSSL-related errors, you might have seen something like:

Error running '__rvm_make -j8',
please read /Users/username/.rvm/log/ruby-3.4.1/make.log

Or perhaps the dreaded:

OpenSSL is not available. Install OpenSSL and rebuild Ruby

The Solution: A Fresh Start Approach

Sometimes the best way forward is to start fresh. Here’s our battle plan:

1. Clean House: Remove Old Version Managers

First, let’s remove any existing Ruby version managers. They’re like having multiple GPS systems giving you different directions – not helpful!

# If you have RVM installed
rvm implode

# If you have rbenv installed
rm -rf ~/.rbenv

# Clean up any remaining pieces
sudo rm -rf /usr/local/lib/ruby
sudo rm -rf /usr/local/bin/ruby
sudo rm -rf /usr/local/share/ruby
rm -rf ~/.gem

2. Install Homebrew in the Correct Location

On Apple Silicon Macs, Homebrew needs to live in /opt/homebrew, not /usr/local:

# Uninstall existing Homebrew (if it's in the wrong location)
/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/uninstall.sh)"

# Install Homebrew fresh
/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"

# Add Homebrew to your PATH
echo 'eval "$(/opt/homebrew/bin/brew shellenv)"' >> ~/.zshrc
eval "$(/opt/homebrew/bin/brew shellenv)"

3. Install ASDF Version Manager

ASDF is like a Swiss Army knife for version management – it handles multiple languages beautifully:

# Install ASDF
brew install asdf

# Add ASDF to your shell
echo "\n. $(brew --prefix asdf)/libexec/asdf.sh" >> ~/.zshrc
source ~/.zshrc

4. Configure OpenSSL

Now for the secret sauce – proper OpenSSL configuration:

# Install OpenSSL@3
brew install openssl@3

# Set up environment variables
export LDFLAGS="-L/opt/homebrew/opt/openssl@3/lib -L/opt/homebrew/opt/readline/lib"
export CPPFLAGS="-I/opt/homebrew/opt/openssl@3/include -I/opt/homebrew/opt/readline/include"
export PKG_CONFIG_PATH="/opt/homebrew/opt/openssl@3/lib/pkgconfig:/opt/homebrew/opt/readline/lib/pkgconfig"
export RUBY_CONFIGURE_OPTS="--with-openssl-dir=/opt/homebrew/opt/openssl@3 --enable-shared"

5. Install Ruby and Rails

With our foundation solid, let’s install Ruby and Rails:

# Install Ruby plugin for ASDF
asdf plugin add ruby

# Install Ruby 3.4.1
asdf install ruby 3.4.1

# Set it as your global Ruby version
asdf global ruby 3.4.1

# Verify installation
ruby -v  # Should show 3.4.1 with PRISM

Now for Rails:

# Install Rails 8.0.1
gem install rails -v 8.0.1

# Verify installation
rails -v  # Should show 8.0.1

6. Create Your First Rails 8 API

Let’s test our setup with a new Rails API project:

# Create a new API-only Rails application
rails new my_api_app --api

Bonus: Shell Configuration

Here’s a clean, organized .zshrc configuration that ties everything together:

# ASDF Setup
. /opt/homebrew/opt/asdf/libexec/asdf.sh

# Ruby/Rails Configuration
export LDFLAGS="-L/opt/homebrew/opt/openssl@3/lib -L/opt/homebrew/opt/readline/lib"
export CPPFLAGS="-I/opt/homebrew/opt/openssl@3/include -I/opt/homebrew/opt/readline/include"
export PKG_CONFIG_PATH="/opt/homebrew/opt/openssl@3/lib/pkgconfig:/opt/homebrew/opt/readline/lib/pkgconfig"
export RUBY_CONFIGURE_OPTS="--with-openssl-dir=/opt/homebrew/opt/openssl@3 --enable-shared"

# Auto-set Ruby version on terminal launch
. /opt/homebrew/opt/asdf/libexec/asdf.sh && asdf local ruby 3.4.1

Troubleshooting Tips

1. Getting permission errors? Try running sudo chown -R $(whoami) ~/.asdf
2. Rails command not found? Run asdf reshim ruby
3. Still seeing old Ruby versions? Check your PATH with echo $PATH | tr ':' '\n' and remove any duplicate entries

Conclusion

Setting up Ruby and Rails on Apple Silicon might feel like solving a puzzle blindfolded, but with the right approach, it’s totally manageable. The key is starting fresh and ensuring everything is properly configured for the M1/M2 architecture.

Remember: A clean development environment is like a well-organized kitchen – everything has its place, and cooking (or coding) becomes a joy rather than a chore!

Additional Resources

• ASDF Documentation
• Ruby on Rails Guides
• Homebrew on Apple Silicon

---

Last updated: January 2024