Did you delete the original book before reloading the one with the calibre metadata? And is calibre you are using the most recent one? Not all of the calibre series could do this. The books on the kindle look exactly the way I change them in calibre. In calibre you can change the order of the series (or rather, put them in correct order) simply by making the first book in a series, the most recent book published. Then it will always appear first.
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