I use Windows and MacOS, and I wince every time either of them has an update.

For one, MS doesn't test updates anymore. You may get something pleasant like losing the ability to print, or having all your network cards vanish.

I had a stack of Mac Minis years ago that I used for various things. One update bricked half of them. I was able to fix them easily, but it should not have happened at all. I installed from scratch on one of them, and an update bricked it. I did nothing to the computer in between the fresh install and pressing the update button. Neat.

The bottom line is Apple and MS have long ago stopped caring about the quality of their products.

Microsoft famously canned their entire group of people who do testing (SDETs). If the problem you hit isn't caught by an automated test at build, Microsoft employees running it in some form of "dogfood," or the people running beta builds, it is getting shipped.

Maybe that's good enough. Maybe people are getting used to software coming out with multiple updates per quarter to fix some "random glitch."

I look at it as the computing industry getting away from the roles and pace that made computers reliable instead of just functional. We used to have Operations staff to keep a service reliable; we used to have Testing staff to make sure a code base was reliable. They had their own failings, but to cut them out entirely did wonders for stock prices and not much for the end user experience.

But maybe being able to launch a pre-VC startup with one person and a stack of cloud services is a better trade-off.

> I had a stack of Mac Minis years ago that I used for various things. One update bricked half of them.

That happened to a former manager of mine when he pushed out an update (might have been High Sierra?). 30 signage machines got sent to surplus as a result, including some that were mounted in some incredibly inconvenient places (which I got to retrieve, of course).

> Normally coworkers are excited to update and get new features.

Really?? I'm a software engineer and I'm usually pretty loath to install major updates because there's usually a greater chance that something will break, costing me hours in fix time, than I'll actually get something super useful that will improve my workflow.

Maybe I sound a little "old school", but I think for most people that at least for the past decade OS updates have been so minorly incremental that any individual update is more likely to cause pain than pleasure. This follows most "mature" technology patterns, e.g. in the late 90s and 00s there was always a pretty good reason to update your mobile phone, for example, but for the past 7 or 8 years the updates have been quite minor (slightly faster processor or better camera) - I really don't feel like I have any significant reason to upgrade until mid band and mmWave 5G become widely available.