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I'm having a similar problem. It's aggravating because when I made my App for watchOS 5 last year there were no issues and now there are issues. My problem is that the phone and watch are not always 'reachable' even though they are right next to eachother. I figured this out because when I try sending a message to the watch, it sometimes prints false when I print 'WCSession.default.isReachable' but sometimes it prints true. Hopefully this is justg something wrong with my personal devices or something like that. I don't want the users of my App to experience issues over something that I can't fix.