In No Particular Order

@vmanot

AirPods <> FaceTime interaction increasingly becoming an open joke.

lldb being unable to inspect local Swift variables in 2024. Swift was released almost a decade ago.

Entirety of Xcode's "Add Package Dependencies" UI. The search bar's text input still missing a debounce despite years into release.

StartDiveIntent. (SiriKit overall along with the gutting AppleScript about 5-7 years too early).

Messages app search indexing (or lack thereof).

Xcode

Dev-rel around SwiftSyntax's coupling with SwiftPM

@dimillian

List There is still no definitive way to keep the scroll position

List Prepending items while scrolling makes the list lag and loses its position

List Micro stuttering even with simple row views

List No control over animations when updating the state

@rdev

NSTrackingSeparatorToolbarItem which was added the same year SwiftUI app lifecycle released, is still not available from SwiftUI.

Focus state management in SwiftUI. Or out of SwiftUI. Anything to do with responder chain in macOS feels intentionally designed to traumatize developers.

@parth220

Apple Developer Enrollment can happen on MacOS, iPhone, and Web. The enrollment processing state machine is nondeterministic. Verification is hit or miss, some people get double charged, random delays on account activation.

@PatrikTheDev

If you have an expired payment method before starting Family Sharing and are not the organizer, Apple will not let you pay for a Developer Membership (because your card is expired) but they also will not let you change it (generic error message).

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PRs welcomed (merging is at the discretion of my personal amusement).

Be civil. Do not target people. Highlight the obscene.