Originally Posted by
KingBuick If it doesn't update automatically that's ok. It'll still update but some of the information will be out of sync.
I'm sure the Watch will update to
some current information. What I'm not sure of is if messages that have been sent while the Watch is
off, will be updated.
I believe apps will update when the Watch starts up. Recently I was watching an update for an installed app, and it didn't until I uninstalled it in the Watch app and reinstalled it. This was quicker than rebooting the Watch.
iCloud based stuff like your Calendar should be updated. Let us know if your Messages get updated and what doesn't.