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If you only had one device plugged in then check that you have the Kindle 2/3 device driver enabled under Preferences->advanced->Plugins->Device Interface Plugins. However that is only required if you are going to use USB as the way of transfering books from Calibre to your Kindle.
In terms of push wireless transfer to the Kindle, this is normally done by emailing the books (via Amazon) to your Kindle. There should be information about how to do this in the Calibre User Guide. It should also be possible to pull books off the calibre Content server via the browser built into the Kindle - but I guess a response from soneone with a Kindle is required to know if that will work.
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