I've been searching around for a while now and I'm hoping for some help here. About a month ago I ripped a CD and it wouldn't sync to my iPhone.
I am using:
Windows 7, iTunes 22.214.171.124, iPhone 5 64GB, Toshiba M700 if that helps.
My library and associated files are kept on a NAS drive.
Over the last month I have restored my iPhone, rebuilt my library, restored my iPhone again after more issues with syncing playlists and music and even installed iTunes on another computer to see if that would make a difference (it didn't).
Now, new songs (unless bought from iTunes and downloaded direct to my phone) don't sync across. Changes to artwork don't sync across. New or adjusted playlists don't sync to my phone.
I would check two things, one create an new file by right click and convert song. Then try to sync and see if it moves the newly created song go over. You can also enable manually mange music to drag and drop the songs you want to your iPhone.
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