I'm a fairly frequent poster/reader over on the forums at Head-fi.org and asked this question over there. I got a few helpful suggestions to ask "the experts" over here so here I am hoping that you'll be able to assist.

Today I purchased myself a 5.5G 80Gb iPod to replace a 30Gb X5L that was stolen. In preparation for moving from file tree to ID3 tag browsing I encoded all my music to MP3 format - I have my entire CD collection archived in FLAC which I use foobar to listen to. I got hold of the latest version of LAME (3.97) and encoded everything into MP3 from foobar. I installed iTunes and imported in all my MP3 files and was able to get hold of all the album art (most of it anyway)

I did notice that every single text field in the tags has a strange character at the end of the data. It looks like a little square a bit like [] but joined together and about half the height and it's at the end of the artist, album & track title fields. This character doesn't show up in foobar at all and even in WindowsXP the data shows up correctly.

Then when I came to sync problems started. After a while (about 10-20 mins) iTunes would crash and any audio files that had been being transferred were unviewable on the iPod. When reconnected with iTunes whatever amount of data that had been copied over was now classified under "Other". I've tried getting it working many times (including Restoring the iPod 3 times) but so far have had no success.

I'm currently attempting a uninstall, reinstall and using a different USB port to sync and (so far) it seems to be working. But does anyone know what the strange character is that's popping up in iTunes and is there any quick and easy way of removing it without having to manually alter every single tag?

Thank you for any assistance that you can provide and thank you for reading this post.

The simple solution is to set foobar2000 to use its "ID3v2 compatability mode" (a.k.a. ID3v2.3), instead of the default ID3v2.4, for tag writing (and rewrite the tags of the concerned files). The "teach a man to fish" variation is to use the forum's search function to find more discussion and information on this topic.

I agree with dv1989, you seem to have run into the bug in iTunes for Windows regarding ID3v2.4. I'd recommend you to change the ID3v2.4 tags to ID3v2.3 tags.

Oh, and please let Apple know you've encountered this bug: http://www.apple.com/feedback/itunesapp.html

Thanks very much. As it happens altering the USB port I was syncing from has allowed it to sync which is great.

As for searching - I did try a bit (admittedly not as much as I could've for which I apologise) but I wasn't sure what terms to search for to narrow down the results to enough topics that I could check.

Thanks again for the answers - I'll update the tags on the files.

It should be as simple as to activate the compatibility mode, enqueue and select all concerned files and then use Tagging > Rewrite File Tags, and shouldn't take too long.