Pulling my hair out (what' left of it). I currently manage my music outside of iTunes, and hold my albums in the format.... Rolling Stones, the - Greatest Hits  ie <album artist> - <album title> [bitrate] I want to add all my music into iTunes, but keep this folder structure. That I know I can do by unticking the boxes on import NOT to let iTunes manage my music, and NOT to copy tracks in. HOWEVER. We know iTunes doesn't have a 'watch this folder' facility. So once I have added all my music in, how do I add future albums ? I prepare music in a temp directory before adding into my structure, so if I add the music from there, then move to my structure, iTunes won't know where it is, as it will have moved from the original adding location. If I move into my structure first, then how will I know which haven't been added into iTunes ? We are also talking a 2tb collection here, so I'm guessing a complete library rebuild every time I add a couple of CDs is also out of the question. Suggestions welcomed !