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I have a Kindle Paperwhite. I also have Calibre, and a goodly number of DRM free ebooks that have nothing to do with Amazon. I'd like to be able to transfer these to the Kindle without the hassle of a USB cable.

I.e. what I'm looking for is to change some setting on the Kindle to make it talk to my Calibre server instead of to Amazon - so that I can disable airplane mode, turn on the wifi and tell Calibre to "send that book to Kindle", and have it appear on the device once it's downloaded.

I don't care about missing out on software updates from Amazon.

Is it possible to do this? If so, how?

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Kindle devices have the ability to receive books via a special email address. Each kindle has a unique address ending in kindle.com. You can use Calibre to send the books via email to your kindle through your own email address. However, if the end goal is to bypass Amazon entirely, this method would not suffice.

Before sending any books to your kindle email address, your sending address will need to be added to your document "whitelist". You can find this list of permitted senders on Amazon by navigating to "Manage my Content and Devices", selecting "Preferences", and scrolling down to "Personal Document Settings". You will then need to configure Calibre to send emails; when doing so Calibre's FAQ recommends sending the email through a known service, as sending the mail directly may lead to it being dropped as spam along the way.

The options for configuring send to email can be found in Calibri's Welcome Wizard.

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