When dragging and dropping, the files are put at the end of the playlist and there's no indicator showing where they will be dropped, like when dragging files around within a playlist.
This is currently related to a limitation of the SDL2 library. Once Tauon is ported to the future major release of SDL3, this bug will likely become fixable. But for now it isn't easily fixable.
When dragging and dropping, the files are put at the end of the playlist and there's no indicator showing where they will be dropped, like when dragging files around within a playlist.