I have exactly the same problem, transferFile does not seem to work at all in simulators for watchOS 6 and iOS 13 but does work on actual physical devices.Interestingly the same code works without problems for a watchOS 5 and iOS 12 simulator combination, so you could try and older watchOS / iOS simulator combination in case you want to test on simulators.
Onranym
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Can confirm same situation in Xcode 12 beta 2 - I updated my feedback with new sysdiagnose files, hopefully this will be fixed soon.
Same for me on beta 3, updated my feedback reports with new sysdiagnose files. Hope this critical bug gets fixed soon.
Same for me on beta 4 😢, updated my feedback reports with new sysdiagnose files. Hope this critical bug gets fixed soon.
Yes, I updated my reports again, I guess WatchConnectivity unfortunately doesn't get any priority 🙁
WCSession.default.updateApplicationContext(...)
is now fixed in beta 6 🎉 Thanks a lot 😊
WCSession.default.transferFile(...)
is unfortunately still not working as expected. I've updated FB7812526 with new diagnose files 🤞
WCSession.default.transferFile(...)
is unfortunately still not working as expected neither in Xcode 12 release no in Xcode 12.2 beta 2. I've updated FB7812526 with new diagnose files for Xcode 12.2 beta 2.
Sadly WCSession.default.updateApplicationContext(...) is again broken in a simulator context for watchOS versions after 7.2, and also for all watchOS 8 beta versions so far.
FB9547733 includes some detailed information about the situation with Xcode 13 / watchOS 8 beta.