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Personally, I either use the SmartEject plugin for calibre or the eject right click menu option in File Explorer. Using the eject option from the USB icon in the systray has not worked reliably for me for close to a decade. The one time I looked at what was happening (I had an oscilloscope handy and time on my hands), it seems as if the time that the power was removed from the device was not long enough when using the USB icon to trigger the device into realizing that it was disconnected. However, that eject does finish flushing any unwritten data before the attempted disconnect so simply unplugging the device allowed it to finish the disconnect.
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