error occurred while converting the file ".." An unknown error occurred -50

one particular album

Is there any artwork on those songs, Lee? If so, try removing it. Do the songs convert without the -50 now?

*Skipping songs*
The iPod seems to fail to play all of the occasional track that iTunes, and indeed other PMPs, are happy to play. There is probably some minor technical error in the internal structure of the file which is normally ignored by other playback software but causes the Classic to bail out.

You may like to try scanning the files with MP3 Validator which can find & fix some internal MP3 errors.

Some users have also suggested that completely removing all id3 tags and then replacing the information can be a solution. This can be achieved in iTunes by selecting an affected track, right/option clicking and using the option Convert id3 tags > None. Since some files may mistakenly have more than one tag you may need to repeat this action. Once you have confirmed that no tag is present you can replace the tag information using Convert id3 tags > V2.3 (I believe it is recommended to avoid using V2.4).

Personally I have found files for which these solutions don't work. In this case the workaround is either to re-rip the tracks or get iTunes to re-encode the file, e.g. convert AAC to MP3 or vice versa and sync the newly encoded file to the iPod instead. Because transcoding will cause a loss of fidelity you should keep your original file so that if a future iPod firmware resolves this issue you can put your original files back onto the iPod.

tt2

Any time 🙂

tt2

🙂 Once again I learn something interesting and valuable from tt2.

In particular, I really like the way MP3Val can check for multiple tags ... useful to know in case we get another of the periodic pulses of trouble reports associated with multiple tags on songs. (It's been one of those problems I've known about but had nothing constructive to suggest to people by way of checking the issue.)