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Hello Zod,
Back in the Simple Touch days, the NOOK software would always choose an image labelled "cover.jpg" or "cover.jpeg" to display as the cover and to create the thumbnail. A book with a cover using a different name would get the simple white rectangle showing just the title and author printed.
Early on I got in the habit of changing the name of any image I wanted to use to "cover.jpg". Anything from Project Gutenberg (for example) has some ridiculously long file names for all the images.
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