Hello, I came across the same problem as you. I googled my problem and i found the answer, when you create a playlist, it is 'only' an IITPlaylist. In opposition with the IITUserPlaylist, you are unable to use the method "Addtrack(the_track)". This is why you need to 'populate' it, using the instance "win32com.client.CastTo(the_playlist, 'IITUserPlaylist')"
Here is my test code, in case I was unclear ^^ import win32com.client iTunes = win32com.client.gencache.EnsureDispatch("iTunes.Application") library = iTunes.LibraryPlaylist tracks = library.Tracks nouvelle_playlist = iTunes.CreatePlaylist('test') nouvelle_playlist = iTunes.CreatePlaylist('Deselected Albums') nouvelle_playlist = win32com.client.CastTo(nouvelle_playlist, 'IITUserPlaylist') third_track=tracks[100] nouvelle_playlist.AddTrack(third_track) nouvelle_playlist.PlayFirstTrack() Glad I helped.
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