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Originally Posted by BaenSidhe
Did you drag to the books directory in your library or your ipad? Because when I tried to drag and drop, itunes would crash right away. I think I was dragging to ipad and not to the library, though, since I didn't want my books in yet another location.
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You need to drag it into the library first, and then transfer it to the iPad from within iTunes. If you just want to drag-n-drop to the iPad from within iTunes, you may have to check "Manually manage music and videos" under Options when the iPad is hooked up; I'm not sure how it handles books (I just use the Books tab to choose what to sync).
If you don't want iTunes storing a copy of books in its media folder when you add them to the library, you can go into Preferences->Advanced and uncheck "Copy files to iTunes Media folder when adding to the library." From then on, iTunes will just keep a pointer to the location of files you add to the library.
However, be aware that this applies to everything (movies, music, audiobooks), and if the original file is moved/deleted, iTunes won't be able to find it unless you go in and point it to the new location.
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When you add a file to the library, does it add it to a folder location like Calibre does? I just did a quick look through my itunes folder and didn't see it, but I didn't look that hard.
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If you're using the standard iTunes organization (and haven't followed the instructions above to prevent files from being copied into the iTunes folder), books will be stored in a "Books" folder in your iTunes Media folder, organized in folders by author name.