If you're talking about cover thumbnails Kindle expects those image files to be located at "/.system/thumbnails" (or something like that, hidden "system" folder part I'm certain about) on Kindle drive (so that would be "/mnt/us/.system/" when using SSH) and to use a certain filename template.
When you transfer books using Calibre's "Send to Device" button Calibre takes care of that, but since you're doing thing manually over SSH you would need to take care of that job.
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