This is amazing! I do not know why it is not touted as a feature of iTunes. I do not know if this existed in earlier versions or not, but it is a very nice feature.

I ripped a CSNY boot and of course I get "Track 1" etc, etc. I have the files in a playlist in iTunes 4, and am renaming them in the Finder, thanks to finding a track listing online. When I rename the file names, iTunes 4 makes the ID3 Name the same thing! I imagine you have to have the files open in a iTunes playlist for this to work. But man, what a time saver!

You may have to double click on the track in iTunes, probably to refresh, but it works!

Also, this little trick only works if the file started out life as "Track 1.mp3" etc, etc. If the file name is already named, and you rename it, there is not dynamic rename in iTunes. Now if the file name started as "Track 1.mp3" you can rename it as many times as you want, and iTunes will update the ID3 info. I only wish this worked on renaming files as well. But for what it is, it is a very cool feature.

Originally posted on Breaking Windows.