I also tried re-installing on the watch, still no luck. What is the expected result? A) remainingComplicationUserInfoTransfers will always be set to a positive number OR B) Even if remainingComplicationUserInfoTransfers is 0, transferCurrentComplicationUserInfo(_:) will still function instead of falling back to transferUserInfo(_:)

I also power cycled both iPhone and watch, with no luck.

It would be awesome if it did. This is as close to an answer as I've found, so thanks for that. However, when I log remainingComplicationUserInfoTransfers I still get 0 after using up the allotment earlier today. Is there another step I need to follow? I uninstalled and reinstalled the app from Xcode after toggling this setting.