In rare cases, your watch may say you are not logged in or your are not a premium member, even though you logged in on phone or upgraded to premium on phone. This is a problem with Apple WatchOS's communication. Apple has asked us to help log the problem so that they can debug and fix.
If you are experiencing this problem, Apple and us would appreciate you follow the procedure here to enable some logging.
First, follow instruction here to download a provision profile, this enables some debug logging for Apple Engineers.
If you do not have a developer account, you can also download the provision profile from our website http://vimo.co/watchOSlogging.mobileconfig
Once the provisioning profile is installed, logout then login (if you have login issues) or restore purchase (if you have premium status issue), Apple should log the event why the status is not sent to the watch. Follow the instruction to copy over the logs, then email them to us. We will file a bug report with Apple so that their engineers can take a look.