http://www.logitech.com/assets/30072/documentation.pdf

This has a section on iTunes and may help.  

You could also post at the Official Forum but this forum sees more
activity.

http://forums.logitech.com/t5/Wi-Fi-Music-Players-Squeezebox/ct-p/squeezebox

I do not use iTunes so am probably not of much help. I am sure there are
many who do use it, hopefully some will chime in with ideas.
My guess is that it is at least partially a tagging issue.

Good luck


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