Best way to look at it, there are two ways to label your MP3s. The first way is just to change the title of the file. The second way is to change the tag which is what most programs read.
Try this tool out, pretty handy.
Download the tagger and CD lookup tool.
I also doubt its an OS issue, most of the time it boils down to user error. Make sure you've updated the software you're using.
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