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@Kuliand
It does send it wirelessly to your kindle as long as you're in Wifi range. You do get an email back from Amazon saying your documents are ready but that's just an alternate option so you can do a USB transfer instead.
I transfer all of my stuff to my Kindle this way, even though I have a 3G I don't want to pay for transfers so I do everything via my @free.kindle email. I have mine setup so that every day Calibre collects my favourite newsfeeds/blogs and sends them to my Kindle so when I wake up they're ready to go, no fussing with hooking my kindle up to the PC to transfer it since its all done wirelessly.
You do have to "register" allowed email addresses on your Amazon page so they can send your Kindle documents, even if its to the free version. If you don't have this setup then the documents probably won't make it to your kindle.
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