I've recently upgraded to iTunes 5.0 on both my Mac and my PC. The Mac version works just like it should; however, my PC version seems to have lost the ability to keep the music folder organized. Regardless of whether or not the box is ticked in the preferences, there doesn't seem to be any effect on the file structure. Changing the tags on files (for example, renaming a track, changing the artist or album name, etc.) leads to no change in where the files are located. Moreover, when removing files from the library, iTunes no longer asks me if I would like to remove them from the disk (all of my songs are located in iTunes' music directory). I tried uninstalling it, deleting all the preference files in "Documents and Settings", deleting the library files, deleting all instances of iTunes out of my system registry, then reinstalling it. I even set my music directory to my second hard disk and let iTunes copy all my files into that directory and it still will not keep the directory organized after the original copy. Has anyone else encountered this? I'm out of ideas here.