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If the issue is another program such as windows media Calibre would not eject and would report something about another program keeping it open. This happens to me when I am too quick to eject after a task.
When Calibre is successful the device icon disappears but Kobo still reports a connection. Never had a problem disconnecting the Kobo after the icon disappears from Calibre.
I use Calibre on my Linux computer and rarely on the Windows 7 computer. I am not a Python expert but wouldn't Calibre just use a system call to eject the usb device? The same call ejecting from a file browser or the task bar in windows would use?
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