Don't you just love when someone shows you something that makes you realize you've been doing whatever it is you've been doing bass-ackwards? Yeah. So, Calibre and iTunes. I had been doing it the hard way, pulling my Calibre library over to iTunes from within iTunes which was causing all kinds of problems. Some books (not all, just a few select scalawags) would always repeat and cause doubling of books for reason beyond my ken. I would have to either dig down through the file structure of the Calibre library and pluck books individually or erase all the doubled books, and... tedious! Here's how to make it happen neat and happy. First, make sure you have the latest Calibre (0.7.27 as of this posting) Quick start: 'Connect to iTunes' mode Launch iTunes with no connected iDevices. Launch Calibre, set Preferences: Preferences|General|Preferred output format to EPUB and while you're there, make sure you also check the No SVG Cover box otherwise your book covers wont show up and if you are as picky as I am about covers and artwork.... Preferences|Conversion|Page Setup|Output profile to iPad Preferences|Plugins|Device Interface plugins|Apple device interface - click Enable/Disable plugin so that driver is disabled (Yes, disabled. Grayed out) Restart Calibre. Select Connect/Share↓ and from the drop down select Connect to iTunes to connect iTunes as a Reader. Now when you add a book to Calibre, you can simply send the one or two or three book(s) directly to iTunes (Send to Device)without any muss or fuss. It works simply, cleanly, and intuitively in a very Apple kind of way. All of the settings will remain as you have chosen from there onward save for one. Whenever you open Calibre, you have to do the Connect/Share and then Connect to iTunes bit. A big (and I mean BIG) thank you to Mickey 330 (Marilyn) for pointing me in the direction of this information!