We have an Apple Watch app and companion iPhone app that we distribute via Enterprise Distribution using OTA manual installation. (We are on an Apple Enterprise Developer Team) With WatchOS 26.4 and earlier, the app would install fine on both the phone and the watch. However, after updating to WatchOS 26.5 (and iOS 26.5), the app will not install on the watch. It will install on the phone and we can trust the developer/run the phone app. However, when we go into the Apple Watch app on the phone and choose "Install" for the app, it tries to install for a minute and then returns an error "The app could not be installed at this time". We have tried the following remedies: Restarting both watch and phone, and reinstalling the app on phone Factory resetting both the watch and the phone, then reinstalling app Generating a new Distribution Certificate and new manual profiles for the app in Apple Developer Looking through console logs from both the phone and the watch Confirmed that we can install other (non-Enterprise) apps on the watch Try installing a basic example app (the default Xcode watch + companion app project) There does not seem to be anything obviously amiss about the app or its packaging, it seems to be something to do with the update to WatchOS 26.5. The closest related errors we have found seems to be these: appconduitd 0x16d43f000 -[ACXInstallQueue _onQueue_deQueueNextOperation]_block_invoke_3: Failed to install app .EnterpriseInstallTest.watchkitapp (p = Y, ui = Y) : Error Domain=ACXErrorDomain Code=8 "Failed to create socket" UserInfo={NSUnderlyingError=0xcf9138e10 {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} appconduitd 0x16d89f000 -[ACXCompanionSyncConnection _installQueuedOrCompletedForWatchBundleID:companionAppBundleID:withName:userInitiated:withError:withCompletion:]_block_invoke: Failed to install app .EnterpriseInstallTest.watchkitapp : Error Domain=ACXErrorDomain Code=8 "Failed to create socket" UserInfo={NSUnderlyingError=0xcf9138e10 {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}