I've always had it set up to back up every time connected on that 2nd page. It just doesn't work so I don't know if I'm missing something. (I'm so new to Kobo and barely figuring the basics out so not comfortable diving into whatever NickelMenu is yet. I've made note of it though. Seems so odd one would have to reboot a device before connecting every time. My kindles were always so easy to use. Simpler system than Kobo though of course.)
https://photos.google.com/photo/AF1Q...P0OGen3m_bvEvo