Sam Soffes

I’ve been using Homebrew on Apple Silicon for a few weeks now and it’s been working well.

With Ruby 3.0.0, I haven’t had any issues installing it with rbenv. Today, I needed to install an older version and had some trouble getting it. Here’s what I did to figure it out. (This assumes your Homebrews are setup like I described in my post.)

First, install rbenv with your native Homebrew:

$ brew install rbenv

If you already have readline installed, you’ll need to uninstall it while installing the old Ruby:

$ brew uninstall --ignore-dependencies readline

Now we’ll need to install OpenSSL with the Rosetta Homebrew:

$ ibrew install openssl

Finally, we can use Rosetta to install an older Ruby (in my case, 2.7.2). This uses Rosetta when building and makes sure it uses the Rosetta version of OpenSSL you installed with ibrew.

$ RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(ibrew --prefix openssl)" arch -x86_64 rbenv install 2.7.2

If you are using Nokogiri, you’ll have some issues with the Ruby you just installed. Here’s how to get it working:

$ ibrew install libxml2
$ gem install nokogiri -- --use-system-libraries --with-xml2-include=$(ibrew --prefix libxml2)/include/libxml2

If you’re still having trouble with Nokogiri, checkout their normal installation guide.

Now, reinstall readline if you uninstalled it above:

$ brew install readline

Kind of a pain, but the speed of your fancy new Mac is worth the hassle, right?