My experience has been the opposite, especially since Rails has included more batteries over the years. You need fewer non-Rails-default dependencies than ever, and the upgrade process has gotten easier every major version.

> What does this mean? The computer isn't alive.

But they want you to think of it as alive. They're anthropomorphizing it.

My org (USA) was affected. I wasn't the primary person dealing with it, but from what I gather one user marked one of our emails as junk, and then suddenly all of our emails to Outlook users started getting blocked.

The update check is HTTPS, only the files themselves are HTTP.