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Group Steps Challenges continuously say "Please sync your watch", but the watch IS sync'd!

This has been happening for 2 months now, for my son's Instinct and using Connect IOS.

It's working fine on my Android Connect app / Fenix, and his mother's IOS Connect app and her Venu 2. But my son's starting having this issue 2 months ago (after working just fine for a year) and we have not been able to resolve it.

What happens is, he opens his Connect app, and his watch syncs just fine. His daily steps show up on the main screen and everything. But when he opens any Group Steps Challenge, his steps are shown as 0, and it displays a message that he needs to sync his watch to have his steps added to the challenge. The message also includes a "sync now" button, but when you press it, it does nothing.

We've completely uninstalled Connect from his phone and reinstalled it, added the watch again, and the same thing is happening still. It's frustrating for him because the Steps Challenges are his favorite thing to do with the watch. I'm quite certain it isn't an issue with his watch, because as I said, it sync's just fine on the daily overview page in the Connect app, but for whatever reason it's just not adding any data to his challenges. It's almost for sure a Connect IOS app issue, but I don't know what else to do besides reinstalling it, which I've already tried.