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This helped me, but I had to put my phone simulator back to 12.4 to get bi-directional communication, even with Apple's own code at: https://developer.apple.com/documentation/watchconnectivity/using_watch_connectivity_to_communicate_between_your_apple_watch_app_and_iphone_appThis was specific to file transfers using WatchConnectivity. I filed a radar for this, expecting it to be a duplicate.