So I just activated this feature on my PC/iTunes, and all Playlists that I’ve had set within my iTunes Library uploaded to iCloud Music Library without problem. However, if I attempt to add a single new song from my PC to an existing Playlist - that entire Playlist gets removed from iCloud Music Library. Why is that? I figured it may work if I create a brand new Playlist, add new songs - nope, that Playlist will not upload to iCloud Music Library. The only method that works is by dragging new content into the standard ‘Songs’ directory within iTunes, which uploads new content without issue, and then on my phone I can select the newly uploaded content and manually assign it to an existing Playlist manually one by one. Well, cool. But how about when I have a Playlist in mind of say 100 songs, when my existing library is over 10,000 - 1) I will never find the newly uploaded songs in that mess 2) adding each song one by one would be extremely time consuming. I have to be missing something, surely there has to be an easy way to drag over entire Playlists into iCloud Music Library. Any help would be so much appreciated.