Walt Mossberg calls out several examples of Apple’s software failing the “It just works” test. I think this is a pretty reasonable rebuke that notes the problems without making unfounded conclusions based on them like Apple being in a slow, inevitable decline that started when Steve Jobs died because, as we all know, he personally conducted code reviews on everything.
I do feel like Apple isn’t quite as good at this as they used to be, although it’s impossible to quantify. Maybe it’s scale, maybe it’s focus, I don’t know what it is. But at the same time, I’ve used some of their competitors’ software and I certainly wouldn’t say it’s any more reliable or user-friendly. Parental controls on my son’s Windows 10 machine just up and stopped working one day. Site blocking just didn’t work anymore. Checking Microsoft’s support forums I found people complaining about this all the way back to Windows 7. Meanwhile, his Live account is completely borked and is inaccessible on our Xbox. Every attempt to access it loads a whimsical Xbox character that says “Uh oh… that shouldn’t have happened. It appears you’ve found a glitch in the system. Please try again later.” Like the error isn’t aggravating enough, having it delivered by a cartoon is adding insult to injury. Also “later” in this context apparently means on a geological scale because no amount of waiting clears it up.
Microsoft’s screw-ups don’t excuse Apple’s. But it doesn’t seem like these companies have learned yet how to perfectly manage an increasingly complex and interconnected set of devices, profiles and data.