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@Scarlet - just to back Nyn up on this. The workflow that I recommended to my Dad that I use also is simply "Plug it in" and "Send to device", then "Create collections" (plugin), "Eject", and finally restart the Kindle. Every time he puts the latest batch of books onto it.
We only use plugin generated collections, with any Kindle only ones like ~Reading~ just marked as an exemption in the plugin configuration and only managed on the Kindle itself. Keeps things simple once it is setup.
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