In the past, on a simulator, I rejected that prompt to test my app. The app still worked as if it were offline (exactly as I expected) until I went to settings.app and entered my password there. This time around I’m on a device, I never see a prompt, and settings says icloud is fine and dandy.

That’s where it will prompt you to re-enter your password if you never got a dialog or dismissed it. That was the first place I went when I got this error, but everything was fine in settings sooo……