File format not supported after syncing from iTunes

So I had made a new playlist folder with sub playlists within iTunes aka Music and moved some new music I had added to iTunes that day into that particular playlist folder/playlists. I opened rekordbox like normal, let itunes sync with it and synced my thumb drive with the new playlist folder. When I got to my gig, none of that new music was in the playlist plus some music that I had copied over from an existing playlist in iTunes. Only music that was there were things that had long since been in other playlists that I’d copied into the new playlist folder/playlists. When I looked in rekordbox today after running OS update and rebooting, I saw the red circle with a line next to all those files that didn’t sync to the thumb drive. When you hover over, it says file not supported, but I ran a test and just created a test playlist directly in rekordbox and dragged one of the same files from my desktop in and it analyzed no problem. So it’s clearly an issue between iTunes and rekordbox. Anyone have this experience recently?