IPOD Classic chokes on only certain MP3 files


I have an odd problem that I'm hoping someone can here can shed some light on. I have certain MP3 files that play fine in foobar, winamp, itunes, and my 5G and 3G IPODS but will NOT play on the new IPOD Classic 160GB. I've narrowed the problem down to something about the IPOD firmware on the Classic that "chokes" on certain files only. A person in another forum has suggested that the problem in his case is that somehow a ID3v2 tag shows up twice in the file and this causes the problem.

Can't tell much from looking at my problem files with a hex editor and was hoping someone here that is more knowledgeable about the file contents could take a look at one of my problem files (I can email or post somewhere).

The behavior is that these "bad" files will start playing in the IPOD (showing correct album art, song title, album name, etc.) but after 2 to 4 seconds will skip to next song. If I move later in the song and hit play, it will also almost immediately skip forward to next song. When a song is "bad" almost every song on that album is also bad (but not all, maybe 90% won't play).

A few specifics:

  1. IPOD Classic 160GB with updated firmware to latest (1.0.3) and ITUNES with latest version (, all running on Windows XP (with all updates, etc.).
  2. I have over 50,000 mp3 files and only a handful exhibit this problem (at least so far, but I have randomly played 1000s of these files and only a few have been bad).
  3. "Bad" files play fine on old IPOD (5 gen and 3 gen), and on ITUNES, WINAMP, FOOBAR.
  4. Encspot and Foobar "verify integrity" do not find any problems with files.
  5. Files that are bad are older MP3 encodes from fhg codec, CBR 192 (done with old MusicMatch 7.5). All files had replaygain info added by fb2k.
  6. tags are both ID3v2.3 and ID3v1.1
  7. I have used "rebuild mp3 stream" and stripped out tags and added new tags (with both fb2k and mp3tag), and problem files remain problem files.
  8. Removing files from ipod and itunes, and restoring ipod and adding files back to itunes and ipod does not help...bad files remain bad.

Of course I have solved the problem on the files I've discovered by reripping (which I now encode to FLAC for archiving and then create vbr lame mp3 files for the IPOD, all using dbpoweramp). But I'd really like to determine what it is about these files that makes the IPOD choke on these particular files. And for a few files I have where I no longer have original to rerip, I'd like to figure out a strategy to "repair" the bad files. Thanks in advance for any help on this odd problem.