In 2023, I wrote this guide to getting familiar with Ruby and Rails for my employer, Super Good Software. In 2025, I wouldn’t change much too much about this article, which, I think, is a testiment to how mature and developer experience-focused the Ruby and Rails ecosystems are.

But I would stop recommending the Pry REPL now. In 2025, even the oldest supported version of Ruby now includes an enhanced IRB that provides many of the features I used to depend on Pry for. One can simply install the debug gem to get even more Pry-like behaviours from IRB.