I'm having the exact same issue, but after coming back to a project after awhile, so I wasn't sure it was related the the upgrade. Thanks for confirming. In my case, I am using OTA install from a companion iPhone app,. but using a normal developer acction (not enterprise) with develop provisioning profiles. Was working great before, but now when I try to install teh app from the phone it hangs for about a minute and displays the "App cannot be installed at this time" error. The Console shows: 0x16f1e3000 -[ACXCompanionSyncConnection _installQueuedOrCompletedForWatchBundleID:companionAppBundleID:withName:userInitiated:withError:withCompletion:]_block_invoke: Failed to install app com.parax.desek.watch : Error Domain=ACXErrorDomain Code=8 "Failed to create socket" UserInfo={NSUnderlyingError=0xa97209aa0 {Error Domain=com.apple.identityservices.error Code=20 "Socket open timed out" UserInfo={NSLocalizedDescription=Socket open timed out}}, FunctionName=-[ACXServerInstallOperation _onQueue_prepForTransferAndInstall]_block_invoke, SourceFileLine=370, NSLocalizedDescription=Failed to create socket} I have tried resetting the watch twice with no success. Definitely seems to be something broken in 26.5. Too bad I can't try to downgrade to verify.