My daugter’s ipod shuffle fell into the dreaded recovery mode loop. Briefly, itunes claims that the ipod is in recovery mode, and must be restored. Restoration and reboot is followed by itunes claiming that the ipod is in recovery mode, and must be restored. The linked discussion on an Apple discussion forum offers various suggestions, most of which either refer to Windows specific issues (no Windows here) or to diagnostic mode (shuffles have no such mode).
I came up with a solution that worked for me. I make no claim it will work for you, but here it is. Fire up the Apple disk utility ( /Applications/Utilities/Disk Utility ). Select the volume corresponding to your ipod, and then select the Erase tab. Yes, the procedure is to erase all data on the ipod. But not just any erase, notice the Security Options button. Click it, and check the Zero Out Data box. The goal is to actually overwrite the data with zeros. In my early tries, simple erase did nothing, but this version did the trick. YMMV. Do keep in mind your music will not survive this process. Don’t try it unless you have a backup or are willing to lose the tunes.
After erasing the data, one more round of itunes restore did the trick. If you try this, leave a comment and let me know whether it worked for you. Good luck.

Posts
Didn’t work for me. I have an iPod 2nd gen shuffle. I’ve tried everything and nothing has worked. I’ve tried this suggestion, I’ve tried the reset utility, I’ve even tried restoring it in Windows and changing the drive number
| January 22, 2009 @ 9:32 pm
Sorry to hear that.
My only other suggestion is to take the shuffle back to an Apple store (assuming it is still under warranty) and ask them to fix it. I did that once. The guy at the genius bar made a few token efforts to fix my ipod, and when the standard approaches did not work, he just exchanged it for a new one.
| January 23, 2009 @ 7:39 am
Unfortunately, mine’s out of warranty, and the real bummer is I only used it about 5 times since I got it. I have an iPod Photo and an iPhone, so I only had the shuffle around for when I needed something really small. My shuffle has never been wet, dropped or abused in any way, and has spent most of its life just sitting on my desk. The recovery loop problem did coincide with an upgrade to 10.5 and a newer version of iTunes, but I don’t think that had anything to do with it.
| February 23, 2009 @ 12:48 pm