Yeah, I can confirm that Calibre doesn't see the new Kobo as a device (yet).
A workaround is after processing the file to Epub in Calibre, choose "save to disk" and point it to the Kobo reader. It saves the files to a folder in the root directory of the KOBO and does basically the same thing as what Calibre would.
Eject the device (using windows USB safe remove), unplug it from the computer and the Kobo will update and show your new addition in the "I'm Reading" section.
btw.. I save all my processed files to a monthly folder and normally just drag and drop the saved folders into the Kobo or onto an SD card. One of the best features of the Kobo is how quickly you can add or remove files since added content is just folders on the root directory of the device.
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