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Originally Posted by ownedbycats
I disconnect, let the book import, then re-connect.
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I misread your steps and didn't see the eject/reconnect. Rereading your steps now, try closing ADE before ejecting the device.
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Would copying the book directly even work? It's DRM'd.
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I wasn't asking you to manually copy a DRM'd book. I was asking you to copy anything. The point was to use the connection to the device by some other method than ADE or calibre and see what happened.
But, you don't need to use ADE to put DRM protected books on the device. You can manually copy them so long as the books are for the same Adobe account that the device has been authorized for.