Apple

ipados sometimes shows me annoying translucent grey boxes in the app menu until I reboot. (I think this is the smallest problem I have with ipados, but I'm sure I could list more)

No mass storage ability without using icloud or I tunes.

Some notifications only have the option to snooze, not dismiss.

When I save things and then go try to find them in Files and they aren't there, only to find out later they ended up in some hidden part of the file system that Files doesn't see.

MacOS — making me go into system settings to allow an app to install that I’ve initiated. I know where the app comes from, I just downloaded it, why do I have to tell my own computer I trust myself to not be an idiot?

iPadOS — multitasking. I know that things are better than they used to be but it’s still a clunky experience to use multiple windows or flip back and forth between them unless you use a keyboard (at which point why wouldn’t I just use a laptop?)

iOS — not a lot these days. I’d still like to be able to customise my Home Screen layouts more, and shortcuts are still pretty unreliable, but I’m largely happy with iOS itself.

watchOS — better customisation for the widgets section. Let me have multiple complication/shortcut blocks, let me organise widgets more easily, etc. More watch faces would be nice too. A lot of the ones that are available are pretty ugly.

Mine is still that (on Mac, at least) the only way to update Apple apps is by updating the whole system. Work requests we don't update our macs, and now I still can't edit texts from my computer.