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Using Calibre and (and 4.23 if DeDRM is needed) is more reliable.
Import to Calibre Library and then Transfer to new device.
Books with DRM won't work by copying without DeDRM plug in for Calibre. Obviously if the two Kindles are on the same account, then:
1) Make sure new Kindle is the default in My Devices
2) Re-download, but using "To PC for USB Transfer". Make sure target is newer Kindle.
Now you can copy from PC to new Kindle without DRM removal, or else install DeDRM and the new Kindle's serial number in Calibre (4.23 as I write as the DeDRM are not yet fully ported to Python 3 for Calibre 5.x or later).
Just copying stuff between Kindles is problematic.
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