I ran into this same issue as well. If you update your project to migrate to a single WatchKit target, you should be able to force immediate updates again. Be warned though, the migration introduced a bunch of build errors into my project that took a couple hours for me to fix, and there are other bugs that you will run into that are specific to a single target watch app: ClockKit complications will break and need to be reinstalled, and location updates will fail if you delete then reinstall your watch app. Quite a mess.