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Originally Posted by Kuram
Is there any kind of wifi/internet push feature for sending books to my device? On my Paperwhite I was able to setup Calibre to send the book as an email to the @kindle.com email address Amazon provides which then had my Kindle download it automatically if it was connected to Wifi. I'm hoping there's something similar for the Kobo.
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No, there isn't. Kobo will sync copies of books you bought from them. You can use the browser to download books, but otherwise, you need to sideload them via the USB cable,
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Also I pre-ordered Oathbringer on Amazon a couple weeks ago, will I be able to load that book on my device (or really any of my previously purchased Amazon books), or will I need to cancel and re-order through the Kobo store (and suck it up & use my PW1 for my old books if I ever re-read)?
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As long as you can get a copy of the book from Amazon and convert it to a format suitable for the Kobo, you will be OK. Just add the book to calibre and when you sent it to the Kobo it will be converted to epub and then sent to the device.