[jscarbo]

If you're a Calibre user, my advice is to forget about using "Send to Kindle" and "Manage Your Kindle". They're awkward, slow and unnecessary.

With Calibre, the best and easiest way to transfer books to your Kindle is to open Calibre, connect your Kindle by usb, highlight the title(s) you want to transfer, and click "Send To Device". The entire process is automated and you can transfer multiple titles at the same time. You can also delete multiple titles by reversing the process. Look for the green checkmark by titles on your device, highlight them, then click "Remove From Device". Be careful to remove them only from the device, not from your Calibre library as well.