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I am seeing the problem with the simulator..but not when running on a real iPad..
Simulator
Version 14.0 (986.3)
SimulatorKit 624
CoreSimulator 857.7
Post not yet marked as solved
Let me join the chorus..I am now having the same problem. After months of everything seeming to work and synch, now the watch never gets 'prepped for development', even though nothing has changed for the watch app portion. Just a useless message box, that provides no update information or status. Apple get on it..it is destroying the development process.
My experience with the M1 MacMini vs my 2015 MacBook Pro Quad I7 was concerning. Building an identical project on both (an IOS, Objective-C iPad app) was FASTER on the 2015 MacBook Pro vs M1 Mac mini.
2015 MacBook Pro i7 - 11.9 seconds
2020 M1 MacMini - 16.5 seconds ...???
I had 32 GB of space left on the 16GB M1 MacMini with 256GB Hard Drive
and about 660GB on my 16GB MacBook Pro (2015 laptop)
My solution/fix ....though I don't understand why this was an issue ...I had 'only' 32 GB of clear space on the M1 SSD hard drive.
But the project is only about 420 MB of files, assets, etc.
I suspected it may have something to do with the disk caching ( the major hangup on the M1 MacMini build was an extremely long time to build the asset catalogue data. After running a disk cleanup utility on the M1 MacMini and cleared up a good 3 GB more space, the build time went from 16 seconds to around 3.7 seconds. Where it was taking just under 12 seconds on the 2015 MacBook Pro.
I used Disk Doctor (from the App Store).. on a whim, and it resulted in a big performance boost...still not sure why.
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Had the same problem with IOS 14.6, Xcode 12.5.1 and the project designed to support IOS 14.1. My fix was to shutdown Xcode, reboot the iPAD, reconnect the iPad. All other steps failed to clear the inability to load the project on the test iPad. Hope this helps.
I had this problem: (MacBook Pro 2015, iPhone 7s, Watch Series 6 44mm), Xcode 12.4, IOS 14.4, Watch OS 7.3 + slow internet)
My solution (as described in another reply) was to Be sure the watch and iPhone work..connect..communicate
de-power the watch (by holding the side button until it reboots)
Then reconnect the iPhone to the computer
Re-power the watch
Wait for the 'trust this computer' to appear ON THE WATCH!
...
Then ..after 2 days of trying everything else..from trying to find folders (that don't exists), reinstalling Xcode, re-pairing the watch, shutting down and restarting Xcode, deleting 'Derived Data', clean builds, etc etc ..and machines..etc..all to no frustrating avail.
...
Hope this helps someone else..maybe?
Post not yet marked as solved
I had similar problem...solution, in Build Settings/Deployment set Skip Install>No ...it was set to yes and it failed as described
Note: Build Settings for the 'watch extension'
..and now it doesn't work again...no a solution (9/26/20)
