ITunes – Sorting issue. Song names that start with ‘the’ or ‘a’

iTunes will put any songs that aren't compatible into a Not Added folder (underneath Automatically Add). If your music wasn't compatible then you would find them in the Not Added folder. So it seems that they are compatible, just not getting deleted.

I would check the permissions on these files and see if iTunes has permission to delete them. Command-i on the files and folder concerned and ensure your use can read and write them.

Another solution is to open the Console.app application (found in the utility folder in Applications) and observe the output of that whilst iTunes is adding the music and see if there are any specific error messages that may point to why it isn't deleting the files.

Here's what finally worked.

1. Copy the file "iTunes Music Library.xml" from Windows to somewhere on your Mac, like your desktop.
2. Change all references to network location of the audio files to something the Mac can understand. For example, all of my MP3 files started with file://localhost//192.168.1.6/music/ So I did a Find & Replace and changed them to the path the Mac mounted my remote music folder: file://localhost/Volumes/Media/music/
3. Clear out the iTunes directory in ~/Music.
4. In iTunes > Preferences > Advanced, uncheck "Copy files to iTunes Meida folder when adding to library".
5. Then import the XML file from step 1 into iTunes by File > Library > Import Playlist.

The "Re-creating the iTunes Library file" section near the bottom of this article helped.