I know that I used to have a huge problem with this when I was using Amazon to convert my personal documents. I'd email a document to the free kindle address, get a file back, have to correct the metadata and then move it over to the Kindle via USB.
Now I email them to my K3 from Calibre over the WiFi and they show up correctly but I'm not sure why? To tell you the truth I'd forgotten that I used to have that problem.
Is it because I'm emailing a mobi file and it doesn't have to be converted?
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