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This is how I managed to have Calibre on my Pixelbook recognize my Kindle device.
As kovidgoyal mentioned, one solution is to use the 'Connect to Folder' method. This is how I do it:
Step 1: Connect your Kindle to your Chromebook. Open the ‘Files’ app. You should see your Kindle listed on the left column. If not, check your cable; ChromeOs should detect your Kindle.
Step 2: Share your Kindle with Linux. For this, right click on the Kindle on the left column in the Files app, and select ‘Share with Linux’. Your Kindle will be shared in /mnt/chromeos/removable/Kindle/documents/Downloads
Step 3: Start Calibre (from the Linux App folder). In the ‘Connect/Share’ drop down menu, select ‘Connect to Folder’ and select the /mnt/chromeos/removable/Kindle/documents/Downloads folder.
A new ‘Device’ menu will appear in Calibre.
Step 4: Configure the device. In the ‘Device’ drop down menu, select ‘Configure this device’. You will have only select mobi, azw, azw1, azw2, azw3.
At this point, you should be able to Select books in your library, and click on ‘Send to device’. They will be converted to the right format and copied to your Kindle. Make sure to properly eject your kindle when done, in ‘Eject your device’ in the ‘Device’ drop down menu, as well as in the ChromeOs Files app.
One remaining issue is that the cover.jpg are not copied, so the books appear without a cover on the Kindle.
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