It’s been over a year with these macOS pop-ups and I still have any idea why an app is asking, what should I say, what is the penalty for choosing Don’t Allow, etc. What a frustrating experience.

(Edit: I’m showing Chrome here but I am getting them for so many other apps without seemingly any rhyme or reason.)

Well, this explains… some things.
I can’t help but think this whole system just feels poorly thought through in terms of design and UX writing. I don’t imagine Digital Color Meter is capturing my screen, and in iOS 26 beta this dialog somehow became even more scary (granted, it’s a beta).
@mwichary the importance lies in what’s dev provided writing and what’s apple provided writing and not being able to distinguish between the two reliably as a user
@tobimori @mwichary 🎯same with like, "App wants to install a helper tool." I used to work on software that used that UI and it got comments from users like "this is vague and scary, please make the popup explain what's happening instead." we would've loved to if we could. and somehow it's still like that.