The iOS Connect IQ app is not updating apps or installing the newest version in some cases. I've had this happen a few times recently
Example: Garmin's own Retro Digital is showing as v1.2.1 on the web App Store but 1.2 on the app. Installing puts 1.2 on the watch and you get a continual 'update' button which does something but not updating to 1.2.1