[chaley]

CC syncs metadata, but it does not sync changes to the books themselves. No calibre device driver does.

One way to get the books to sync is to use the reading list plugin. Set it up to send some list to the device, then add books to that list when you change the book's contents.

Of course, itimpi's comment is germane. Some reading apps might cache book info, so you might not see changes to the book contents even if you resend the book.