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I have been trying to figure this out for hours to no avail.

I have a Kobo Forma that I basically exclusively use to read sideloaded books. I have been trying to organize my library and streamline my book transfer process by using KoboUtilities and Kobo Touch Extended.

Everything seems to work fine; I send a book to my Kobo using Calibre, read a bit, and then everything is fine when I plug it back into my computer. However, the problem starts as soon as I try to read a second book on my Kobo; I plug it back into my computer and Calibre suddenly doesn't recognize the second book as being on the device. This problem also causes my Kobo database to corrupt fairly often.

This only happens when I try to read two or more books; I can download as many as I please without issue as long as their status all remain as unread. As soon as I have more than one of them set as "reading", the problems start.

I don't understand; I feel like there is some small setting in one of these plugins that I'm overlooking. Could it be a metadata problem? I have tried a variety of books (some with tidier metadata than others), and they all cause this same issue. I have also tried using different USB cables in case that was causing the corrupt database. Any help is appreciated!