I use my 3G nano to listen to audiobooks (from Audible) during my commute. It should hold a bookmark. Sometimes it does; but sometimes, when I go to the book, it opens partway, then slides back to a page listing chapters. Going back to the book just starts the book all over again. I can scrub to where I was (I usually jot down the time when I stop it to make this easier), but that's time consuming and annoying. I haven't found any pattern. It happens more frequently after I synch, but not consistently so. Sometimes I synch and all is fine; sometimes I don't and I lose the bookmark. My 2G nano held a bookmark perfectly.