trouble syncing/loading music from macbook catalina to ipod classic

ever since i upgraded my macbook to catalina, i have had so much trouble loading/syncing new music from it to my classic ipod. i will buy a song from amazon or itunes or will load a song from an old cd. when i try to put it on my ipod, it doesn't work by just dragging it to the ipod icon. i find myself dragging it all over, to my desktop & then the icon, clicking it multiple times, deleting it & reloading it, etc. anyone else have this problem? can anyone give me easy instructions for putting new music on my classic ipod via my macbook with catalina?