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BrooksNYC,
Welcome to the Forum.
When your Kindle is connected to your PC, calibre displays the "On Device" column, and lets you know which books are on your Kindle. When your Kindle is NOT connected to your PC, calibre does not display the "On Device" column.
Looking at your screen image, calibre is saying that "The Fire Next Time" is in your calibre library, but it is NOT on your Kindle.
Post back if you can actually read "The Fire Next Time" on your Kindle, and if you can read it using the calibre E-book viewer.
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