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UPDATE: This solved it for me: https://stackoverflow.com/questions/55213319/xcode-error-launching-watchkit-extension/61216907#61216907I'm having a similar issue. XCode won't deploy a simple Hello World standalone WatchOS app to Apple Watch 2 paired with iPhone 7 Plus. When I do 'Product > Run' I get errors saying the device is not ready/paired and I should connect it again. I've connected it many times and it shows as paired perfecty in XCode. Sometimes the iPhone asks `trust this computer?`. I say yes and enter my passcode. The Apple Watch does not show the 'trust this computer?' dialogue. It seems that the Watch should be showing this dialogue according the the error message. Rebooting iPhone and Watch fixed this issue and I got asked to trust the computer on the iPhone and on the Apple Watch. Note you need to enter a passcode after the trust screen, which was quite slow to appear on the Watch. After doing all this and then 'Product > Run' again it seemed to get further with the deployment, but then stopped with a new error 'Device doesn’t support wireless sync'. Both error logs are shown below. I'm wondering if Apple Watch 2 is supported?Error logs below:DetailsUnable to install "HelloWatchOS WatchKit App"Domain: com.apple.dt.MobileDeviceErrorDomainCode: -402653147--The host is not paired with the device.Domain: com.apple.dt.MobileDeviceErrorDomainCode: -402653147User Info: { DVTRadarComponentKey = 261622; MobileDeviceErrorCode = "(0xE8000025)"; "com.apple.dtdevicekit.stacktrace" = ( 0 DTDeviceKitBase 0x000000011ee7181a DTDKCreateNSErrorFromAMDErrorCode + 233 1 DTDeviceKitBase 0x000000011eeb2f70 __90-[DTDKMobileDeviceToken installApplicationBundleAtPath:withOptions:andError:withCallback:]_block_invoke + 155 2 DVTFoundation 0x0000000104850385 DVTInvokeWithStrongOwnership + 73 3 DTDeviceKitBase 0x000000011eeb2ca8 -[DTDKMobileDeviceToken installApplicationBundleAtPath:withOptions:andError:withCallback:] + 1654 4 IDEiOSSupportCore 0x000000011ed29e91 __118-[DVTiOSDevice(DVTiPhoneApplicationInstallation) processAppInstallSet:appUninstallSet:installOptions:completionBlock:]_block_invoke.352 + 4165 5 DVTFoundation 0x0000000104983a10 __DVT_CALLING_CLIENT_BLOCK__ + 7 6 DVTFoundation 0x0000000104985652 __DVTDispatchAsync_block_invoke + 1194 7 libdispatch.dylib 0x00007fff6b03a6c4 _dispatch_call_block_and_release + 12 8 libdispatch.dylib 0x00007fff6b03b658 _dispatch_client_callout + 8 9 libdispatch.dylib 0x00007fff6b040c44 _dispatch_lane_serial_drain + 597 10 libdispatch.dylib 0x00007fff6b0415d6 _dispatch_lane_invoke + 363 11 libdispatch.dylib 0x00007fff6b04ac09 _dispatch_workloop_worker_thread + 596 12 libsystem_pthread.dylib 0x00007fff6b295a3d _pthread_wqthread + 290 13 libsystem_pthread.dylib 0x00007fff6b294b77 start_wqthread + 15);}--System InformationmacOS Version 10.15.4 (Build 19E266)Xcode 11.4 (16134)Second error log:DetailsUnable to install "HelloWatchOS WatchKit App"Domain: com.apple.dt.MobileDeviceErrorDomainCode: -402653057--Device doesn’t support wireless sync.Domain: com.apple.dt.MobileDeviceErrorDomainCode: -402653057User Info: { DVTRadarComponentKey = 261622; MobileDeviceErrorCode = "(0xE800007F)"; "com.apple.dtdevicekit.stacktrace" = ( 0 DTDeviceKitBase 0x0000000121d9681a DTDKCreateNSErrorFromAMDErrorCode + 233 1 DTDeviceKitBase 0x0000000121dd7f70 __90-[DTDKMobileDeviceToken installApplicationBundleAtPath:withOptions:andError:withCallback:]_block_invoke + 155 2 DVTFoundation 0x0000000107823385 DVTInvokeWithStrongOwnership + 73 3 DTDeviceKitBase 0x0000000121dd7ca8 -[DTDKMobileDeviceToken installApplicationBundleAtPath:withOptions:andError:withCallback:] + 1654 4 IDEiOSSupportCore 0x0000000121c4ee91 __118-[DVTiOSDevice(DVTiPhoneApplicationInstallation) processAppInstallSet:appUninstallSet:installOptions:completionBlock:]_block_invoke.352 + 4165 5 DVTFoundation 0x0000000107956a10 __DVT_CALLING_CLIENT_BLOCK__ + 7 6 DVTFoundation 0x0000000107958652 __DVTDispatchAsync_block_invoke + 1194 7 libdispatch.dylib 0x00007fff6b03a6c4 _dispatch_call_block_and_release + 12 8 libdispatch.dylib 0x00007fff6b03b658 _dispatch_client_callout + 8 9 libdispatch.dylib 0x00007fff6b040c44 _dispatch_lane_serial_drain + 597 10 libdispatch.dylib 0x00007fff6b0415d6 _dispatch_lane_invoke + 363 11 libdispatch.dylib 0x00007fff6b04ac09 _dispatch_workloop_worker_thread + 596 12 libsystem_pthread.dylib 0x00007fff6b295a3d _pthread_wqthread + 290 13 libsystem_pthread.dylib 0x00007fff6b294b77 start_wqthread + 15);}--System InformationmacOS Version 10.15.4 (Build 19E266)Xcode 11.4 (16134)