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What about building in a button or setting to delete the documents/{book}.sdr/EndActions.data.{ASIN}.asc file? At least on my KT if I delete these it no longer pester me. This file DOES hold the data for that popup and I guess when it is gone, the Kindle's endaction software think it is a sideloaded book. (Which after calibre, it technically is.) I don't actually have a KPW to see if it works the same there, but I definitely am not getting ANY popups on the KT.
Right now I just do "rm /media/Kindle/documents/*.sdr/EndActions.data.*.asc"
Just make a button/shortcut to run "rm /mnt/us/documents/*.sdr/EndActions.data.*.asc".
This won't be as good as just turning off the EndActions altogether, but if you can't get that working...
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