I absolutely hate these sorts of nagging popups and I’m happy that a vendor I already have to trust doesn’t pop them up when I acquire a new product and sign it into my Apple account.
Imo, if this were to happen, it should happen by allowing devices like the pebble watch to sign into an Apple account and acquire permissions through that process rather than nagging on my phone on pairing.
I think I was pretty clear. You setup your pebble watch via openid connect/oauth like any other API client. No nag popups, manual Bluetooth pairing, etc.