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Troubleshooting Kindle doesn't read sideloaded books via USB

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As the title says, it seems that my Kindle doesn't recognize my books that are sideloaded via USB. Send-to-kindle works just fine, but when I sideload books via Calibre or drag and drop, it doesn't show up on my library. Even books downloaded directly from Amazon's website using the Download and Transfer option.

I thought I just had too many books in my Kindle, so I deleted most of them. But it still won't read sideloaded books.

Any idea what's happening? Or has this happened to anyone else?

I'm using Kindle Basic 10th, on 5.15.1.1

Edit: I have tried restarting, and still nothing. I'm hoping someone has an insight before I proceed with a reset (even though most of my books have already been deleted).

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