Hi Ziqiao Chen, Thank you for your answer and your suggestion. That's a great one and I'm definitely keeping it in my arsenal of debug tools. That said, my problem was so much simpler and stupider. My app was indeed successfully archived, distributed and could be downloaded successfully. The app was purchased properly but needed to be installed by a separate user action by going into Watch's App Store app, navigating to Purchases, and then downloading it onto the watch explicitly. Out of 6 users who tested this (some seasoned Apple and Watch users), none of them knew this and they were all so surprised that a Watch-only app needed to be explicitly installed on the watch upon purchase. Because this is unarguably unintuitive, my fears about releasing the app and being bombarded with 0/1-star reviews have solidified. Thus, I will probably put in a few hours to develop a stub companion iOS app to Act as a user guide Tell the users what to do if the Watch app hasn't been installed automatically. The fact that something will be installed onto the phone will also be a good indicator that something has happened for unaware users. As things stand, the userflow is quite literally broken. There is nothing to tie the download of a watch-only app from the phone to downloading onto watch and firing up the app. This is -in my opinion- presents a terrible user experience. What is normally a one-tap ("Get") action for iOS apps is a massive hassle for watch-only apps. There is an implicit expectation that the users will know that their purchased app will show on on their watch's appstore (which clearly nobody really uses). And this is buried deep under Purchases section, which is also buried inside Watch AppStore app under Account menu for which one has to scroll a lot. I hope though Apple might change this odd userflow to either Automatically install the Watch-only apps onto watch, or Ask the user if they'd like to install either on the phone or on the watch, or Tell the user how they could install. Kindly, p.s. Upon me figuring out what was going on, one of my users found many other watch apps waiting to be installed on his Purchases list (some from a few months ago).

Minor correction to post: my SKIP_INSTALL key is set to YES. This is how xcode created the app anyways.