Open Radar

 
iTunes 12.3.0.44 Mac
iOS 9.0.1
Watch OS2

Performed the Watch OS update from 1.0.1 to 2, when the iPhone app showed complete, it said watchOS was 1.0.1 (and up to date) after the update for a while, then it showed watchOS was 2.0 (and up to date.)  The watch always said watchOS 2 in the setup screen.

When I looked at the watch I found that none of my non-apple apps had been installed on the watch, and the iPhone watch app showed them as 'installing'.  I left the watch for about 30 minutes, and neither of those things changed.

I wasn't sure what to do at that point, as the iPhone watch app showed everything was done.  So I tried powering down the iPhone and restarting it. I let it go for several minutes then checked the watch.  3 of the non-apple apps had started to install and showed progress circles on the apple watch app display.  After allowing them to finish and allowing extra time for more to install, no more installed, and only those 3 no longer showed 'installing' in the apple watch app.  Several other apps still showed 'installing' but no activity could be seen.  I rebooted the iPhone again, and a couple more installed.  I noticed at this point that Dark Sky no longer showed as 'installing', but it also did not appear on the apple watch.  At this point I powered down the watch, and restarted it.  After restart, the Dark Sky app icon was visible on the watch.

At this point, all apps where installed on the watch, and when I tried to run them, I found they worked.  I noticed, however, that they were all watchOS 1.0.1 apps, as indicated by the launch behavior of the spinning circle with the app name in the center of the screen.  In particular, Dark Sky behaved this way.

I then used iTunes on the Mac to sync again with the iPhone.  I had already installed all these apps the same day, because I also updated the iPhone to 9.0.1, however, iTunes then synced 17 apps to the iPhone again, including Dark Sky.

At this point, the apple watch showed the Dark Sky icon, but the app would not launch.  Oddly, the iPhone watch app showed Dark Sky was not installed (slider for app was off) even though the icon was visible on the watch.

Changing the slider to off, waiting a short period, then back to on, installed the Dark Sky app again.  On running the app on watch, it now launched, and the app name was in the upper left at launch as seems to indicate a native watch OS2 app.  The only remaining problem for Dark Sky was that location services were enabled on the iPhone for Dark Sky, but Dark Sky reported that it could not access location.  Toggling location services on the phone off and on for Dark Sky resolved the problem a short time later.