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@danwdoo: It's always been a bit tricky. At one point, the sorting was based on the publication date set in the metadata (IIRC), but I'm not quite sure it works like that anymore on FW 5.X.
I *think* it follows the sorting you choose? i.e. date, author or title?
It's been a while since I bothered checking, I personally just kinda live with it, but I do know that a popular solution is a Calibre plugboard tweaking the title on "Send To Device", ir order to prepend the volume number to the title. Sorting by title on the Kindle then take scare of the rest.
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