I always keep my Kindle Paperwhite in airplane mode because I have no wifi. My Kindle is unregistered, I had to register the Kindle account on the phone. I always transfer books via usb.
It might help if you are consistent in the way you use your Kindle; either always use it in airplane mode and sideload books, or always transfer books via wifi.
It might be worth contacting Amazon via their chat facility. (This can be hard to find: go to 'help' and eventually you'll find a 'contact us' option, choose 'chat' which opens a chat box with an Amazon assistant. If you're lucky, you'll get a techie type who knows what you need.) I've found their service to be excellent, just not easy to find.
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