Microsoft Windows (just Windows, not all the other stuff) is a massive bloat-fest. It's a whole load of interconnected mess, so it's likely impossible to fully test one bit without also testing a load of other stuff too. Then Microsoft also has to test their stuff on a whole room full of different hardware, just to cover their partners, never mind all the other vendors that matter.
There's no way Microsoft can test everything, all the time. It's likely just too big a problem for anything other than maybe a big launch or service pack or something. As such, they likely have to cut down from "fully test everything" to "quick test everything", to "quick test the main bits and call it good".
If there'a any similarity between MS and Oracle here, it's that they've spent decades lumping ever more features into places they don't belong. If (for example), MS had taken a far more modular approach to Windows, then right now, a whole raft of people would be unaffected by this bug because they didn't adopt some lump of services that contains the issue. What's more, MS would be able to internally segregate the problem and so likely would be able to get closer to "test everything, every time" than they can currently, so the likelihood of the bug even getting out would be reduced.
So yeah, there's a wider issue: Far too much legacy software is just too bloated and poorly architected. That poor engineering leads to problem after problem.
(As an aside, I'm reminded of Qnap NASes, as something of an example of "microsoftism". Bear in mind a NAS is supposed to be a "hands off" sort of device - it's an "appliance", so shouldn't demand much of your time.
I now use OpenMediaVault on my Qnap nas because I got fed up of Qnap having severe issues with some bullshit service they'd shoe-horned into their Nas product, which didn't need to be there. Now I have a NAS, and that part of it works really well and doesn't need update after update. I also run some of the "higher level" stuff Qnap offer, like my home CCTV runs on it - but that's entirely separate and so has a completely different update schedule and can be updated without affecting the NAS. I've gone from "shove everything you can possibly fit into it" to "lean, modular and well architected", and have a lot less hassle as a result)