Thank you so much for this quick response! That makes perfect sense so I will give it a wack and report back if I have any questions or concerns.

I ended up nesting a NSHostingController into a NSScrollView and allow AppKit to manage the interaction. That worked best for me since the view I was scrolling wasn't a large list that needed dequeuing behaviors.

When I use a custom formatter, the date no longer live-updates—is this the same for you?

I believe it’s probably a bug - I can confirm that Apples apps have the same behavior. No word from them back on feedback assistant yet.

Thanks for chiming in! Haha yeah… I’ll likely do that today, I’ve got no clue what I am doing :)

What you summed up is exactly along the lines that I was needing to achieve and I think that direction makes perfect sense :D This has been very insightful and likely the best answer I’ve ever received (and maybe even seen) on the forums by framework engineers! Thank you again for that additional follow up and detailed thought example!

Oh wow! Thank you so much for this detailed response, that's about the best answer I could have asked for. For clarification to the situation: I am asking the user what they'd like to do with the app's local datastore that was imported from CloudKit after an iCloud account change (initiated from a NSUbiquityIdentityDidChange notification; there's a few situations in which I need to explicitly have the users response for how to handle the local data such as merging or replacing). It's a weird sort of alert because the message isn't necessarily tired to any window's content, but the app as whole. Theoretically, I could surface this message on all windows and dismiss it when a choice has been made on one of them, but I'd really like to avoid going that extreme :x

In my case, I am doing iCloud account resolution in the app delegate and there’s a handful of situations that require user intervention (for example, if an account changes and I need to ask to merge or not merge data from the new account). I am currently using something like the above to grab the most relevant window to show an alert - is there any recommended way to do something like that for this case?