RailsConf 2022 - Upgrading Rails: Everyone can do it and here’s how by Andrea Fomera

Ever felt overwhelmed when figuring out how to upgrade a Rails app? Unsure where you should begin? We’ll talk about how upgrading should be treated as a feature, and how you can get buy-in from management for upgrading Rails. Have you heard about how GitHub or Shopify uses dual-booting to run two versions of Rails at once and wondered how that works? We’ll talk about three approaches you can use to upgrade your app. You’ll leave this talk with takeaways you can put into practice for your next Rails upgrade.

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[laughingvampire]

I think ruby & rails should be updated continuously as soon as a new version is out. obviously this is done in development and with its own ticket and then let the team know of the results so if there is a breaking change have the entire team upgrade it and not just one, I'm looking at a bunch of companies who kept old unsupported databases & dependencies, I've been though a lot of these teams.