Did you know that if you attempt to configure your pebble from your phone, that requires a connection to some server hosted under a domain name that as far as I can tell has nothing to do with pebble?
Use a MITM proxy and see for yourself.
My firewall blocks outbound requests by default so when I found I wasn't able to configure my pebble without allowing this traffic, I just said fuckit and left my pebble unconfigured. If I knew about this before I bought it I never would have agreed to the purchase.
Edit: Pulled the host that it wants to talk to from DNS logs, zalew.net.pl. If I don't allow traffic to that domain, I can't configure my pebble.
Edit: This is from an Android phone, I can't speak for the iOS app.