It appears simulated rotation no longer works on iPad in iOS 13, due to changes for multi-window support.
It’s worth noting that rotation on iPhone still works 🤷🏻♂️. What’s happening is that -setOrientation:animated: is called with the correct UIDeviceOrientation, but on iPad only, the UIWindow never ends up registering for the UIDeviceOrientationDidChangeNotification notification because its windowScene is unable to receive device orientation events.