Hi @Sean_Scott ---- Thank you for the post and sharing your feedback with us. Both are appreciated.
Moving forward, our knowledge base has very good documentation on how our iTunes integration works and the best methods/practices for using iTunes with Roon. I have listed a few articles for you below. Can you please give them a read and let me know what you have tried already in relationship to our instructions?
Additionally, may I very kindly ask you to please provide me with a brief but accurate description of your current setup using this link as guide.
-Eric
Roon Knowledge Base: “iTunes”
Roon Knowledge Base: “Importing Playlists”