I feel macOS these days starts feeling like Windows in the 1990s where occasionally some core component of it breaks, and a reboot is necessary to restore it to full functionality again.

But even with that in mind: this happened literally right after the reboot, with nothing much happening and no other signs of the system in distress.

It’s hard for me to even understand what would make this kind of thing pop up. Trash feels like one of the core tenets of a GUI – like undo, or copy/​paste, or windows gaining focus. You don’t expect it to just… stop working, especially with a circular error message like the above.

If you plug in a CD drive (he said with a straight face in the lord’s year 2026), and then eject too soon, the system offers this dialog, which allows you to say: Eject whenever you’re done with whatever you have to do.

But more modern media, like SSD drives, don’t show that window. The best case scenario is that you get a dialog box like the 1990s never ended:

It gets worse. Often, you get zero help in identifying what the “programs” actually are. (The word on the street is that it might be stuff like Spotlight indexing, which you can’t really control.)

More often than not I just click Force Eject or jank the drive cable out, which feels really unpleasant. I would guess many people do the same.

So at this point we are two steps worse than the original CD experience, which… wasn’t even that great! A pretty clear improvement on this already exists elsewhere in macOS, and could be reused here – “hey, you don’t have to do anything, just give me a second while I finish up here.”

(Can’t help but notice the discrepancy of visual styles of these windows, and even the inconsistency between calling things “applications” vs. “programs.”)

Reported to Apple as FB21787458.

This appeared when trying to delete (even when trying to Delete Immediately, skipping the trash altogether):

Same thing right after, when trying to tag some existing items, for which I don’t imagine any new space should be necessary:

Also, why are these dialogs so different?

I feel like not so long ago there were literal books making fun of bad dialogs like these.

Reported to Apple as FB21509633.

When you accidentally rename a file to a name that already exists, Finder tells you about it, and then just dumps you out of rename, so you have to enter rename mode again and type the desired name.

This feels like such a 1990s way of doing things: throwing a dialog box and washing your hands away from the responsibility to make things smoother and more fluid.

It’s not hard to imagine a better solution that returns you to rename mode and keeps the name you entered so you can refine it, or even something that eschews the dialog box altogether, and does something simpler like a password shake or a little callout.

Reported to Apple as FB21509667.

I am starting to collect all the problems I routinely find in Finder. I can think of ~15 off the top of my head; maybe this will turn into an essay of sorts. I hope this isn’t too boring for you.

Sometimes Finder takes a really long time to update the list of files after something changed it.

All my screenshots go to a specific folder. In these videos, you can see me taking screenshots with ⌘⇧4 while looking at the folder where they arrive.

The first one is fast – just as fast as it should be. The ones after that arrive with a few seconds of delay that feels completely random.

But this is nothing compared to this, just a few minutes later, where the delay was over 50 seconds. Nothing changed. The computer was not under load.

This happens routinely and feels completely random.

There is also, as far as I know, no way to force a re-sync with a keystroke or a button or a pull-down gesture, which could be at least a way to manually alleviate the symptom (if not the cause).

Hearing what others told me and based on prior experiences, I don’t have high hopes for any of this, but I want to be a good citizen. So I am filing bugs with Apple for all of these. I do not believe I can link to this directly, but the report I filed for this one is FB21444299.