Carsten Dreesbach

Just to short-circuit a certain type of reply: YES, I clearly should have googled the error message sooner

Also this is a great example of the "idiot-genius roller coaster" of software development that I first heard about from @KentBeck - there's the trough of despair, "why can't I get something simple like this working" and then the crest of VICTORY, "OMG I AM SO AMAAAAAZING"

Both are illusions

My point here is NOT “Rails is bad” - most frameworks have this upgrade problem. My point is that we put a significant complexity burden onto app developers to understand their OS - which has no redeeming value except making those of us who figure it out feel superior.

How might we enable app developers to to focus their attention on the app, rather than the environment?

Something that might actually help is if we had officially blessed, up to date STATICALLY LINKED binaries for the major platforms. Both Ruby itself AND all gems with native extensions. But that's a huge ecosystem shift.

I still can’t get over that the OS that most Rubyists use routinely cannot cleanly build Ruby

And, conversely, the OS that most Rubyists take a regular dump on has the One Click Installer: https://rubyinstaller.org/  HAHAHA SCREW YOU WINDOWS DORKS. Oh. Oh wait. You're not listening because you're too busy working on actual work