I have searched this question and I believe I am having a varient issue of this problem. If the watch is the first to ask for a specific HK permission, it shows the prompts on the watch and phone, but no HK permission sheet appears. Thats ok, because for my app, I don't require that the watch ask first.
What is posing a problem for me however, is that if the watch app is the first to be launched (as opposed to the phone app), the phone app with then never ask for HK permissions, even in conditions where it otherwise would. Going into the 'Health' app, and manually changing them has no effect. This problem persists through a reboot.
Currently all my hk-permission requests are done in either 'willAppear()' 'viewDidLoad()'