I am also facing this issue. I can send messages from the watch to the phone just fine.
However, even when the session is activated and isReachable = true, the phone cannot send any kind of communication to watch.
I have tested messages, userInfo transfers, even reply handlers. None of them work going from phone -> watch.
This is a breaking bug for many watch apps - this needs to be fixed ASAP.
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I'm having the exact same problem. Websocket code that worked perfectly on watchOS13 / iOS13 - immediately disconnects and is unable to send messages on iOS14 beta 2 / watchOS 7.