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Lately I've been having the same issue with my Nano. Sometimes it takes 6 or more tries before it will boot the original firmware. When I first installed Rockbox, I could boot into the original firmware without a problem. *shrugs*
If you need to boot to the Apple firmware often, I'd suggest using the iPL Loader 2 bootloader instead. On bootup you'll be shown a menu and you can choose to bootup whatever you like.
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