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)

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?

Similar problem...my iPhone/iPad auto updated, and now it effectively turned my 27 inch 2013 iMac into a useless development tool. This is beyond frustrating. One expensive OS upgrade just stalled years of work..

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.

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.

Having the same problem with Xcode 13.3, M1 MacBookPro..etc. all latest updates on MacBook Pro, iWatch, Xcode etc.

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.

Same problem now occurring on my MacBook Pro m1...anyone have a 'real' solution. So far everything mentioned always ends up with the same stuck result. Spinning blue installing wheel now going for over an hour...unacceptable Apple

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

I had the same problem after editing the Schema. I inadvertently added a blank environment variable. Deleting the blank entry in the schema fixed my perplexing problem. A real head scratcher..

I have have a Norton VPN..not the problem! Unpair/repair..does NOT solve the problem! Initial Fix: Installing Xcode 16.2 Beta Solved the problem with my iPhone 11Max Also solved the problem with installing on iPad 12.9 (6 generation) Now communication/debugging etc is working and not stalled for 'hours'

I agree with many. For those of us who have great working apps that have a look and feel perfectly designed for the last 17 years+. For Apple designers to suddenly determine their 'new' an d probably inexperienced designer change is a 'value add' are grossly mistaken. Give the developers who have designed great apps for decades some respect and don't break the look and feel and/or generate hours or weeks of 'redesign' to fit some new employees 'vision'.