I am running into the same issue now with Xcode 11.6 and the iphone simulators with 13.6 and watch simulators with 6.2.1. The watch connectivity session gets created and setup properly. The watch and iphone simulators create the session, it is supported and reachable. The watch will send a message; yet, the message times out with "Message reply took too long.". This was working before and then stopped working. I have deleted and created both iphone and watch simulators and paired them. I have removed xcode completely and installed it again to no avail.
Any help would be greatly appreciated.
srayhunter
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I have run into the same issue on Xcode 11.6 with the watch simulator 6.2.1 and the iphone 13.6 simulator. It was working at one time and the communication was working fine - than something happened.
The session is created and the connection made and the watch will send a message to the phone; however, the message will timeout. The code has not changed at all. I have deleted the simulators and recreated them. I have uninstalled/installed xcode numerous times; yet, nothing seems to fix the issue. The code works properly on real devices and can communicate.