The classic (pre-Touch) iPods from Apple are pretty good portable jukeboxes, but they have a critical flaw in how they handle certain database problems; rather than try to fix the error, they just reboot immediately, getting stuck in a boot loop. I have seen this happen on several generation of iPod, including the 5G, the 6G/Classic, and several revisions of the iPod Nano.
There are a number of things that can cause this problem, such as the COMM
(comment) field exceeding the iTunes hard limit of 254 characters, or due to invalid UTF-8 byte sequences in ID3 tags (which are pretty common in the wild since ID3’s encoding standard is a bit ad-hoc and nobody can even agree on what it’s supposed to be).
Sometimes you can find the culprit by exporting your iTunes library as XML and then running an XML validator on it – this will find the most egregious encoding issues – but often you simply have to search through your library to find the files which are causing your iPod to reboot constantly. Here is a simple procedure for that.
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