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Using USB cable is a hassle, so I am curious if there could be an easy way to transfer mobi documents wirelessly to Kindle directly excluding Amazon servers? My device is already jail-breaked.
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Yes, it is possible. Look at the usbnetwork hack, specifically its SSH abilities. Basically, the idea is that you turn an SSH server on the Kindle on and send anything to your Kindle directly via SSH. On the client side (ie your computer), you can either use a command line (Linux and Mac OS families typically come with built-in CLI SSH and RSYNC client), a graphical SSH/RSYNC (I believe it is available for any platform instantly by a Google search) or an SSH Calibre plugin (here on MR in Calibre plugins section), depending on your skills and preferences.
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And as WiFi has to be enabled in this situation, how could I make sure that the device is not reporting back to Amazon about my activities. I am a kind of a person who hates when someone is looking over my shoulder to see what I am reading.
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I am not sure but I guess this thread is pretty much what is known about this...