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When playing the currently playing song is not at the the top and the playlist is scrolled down to show some of the previously played songs.

I'd rather see the upcoming songs than any of the previously played songs.

How do I get it to show the currently playing song at the top of the currently viewed playlist at all times during playback?

A representation of how I'd like the playlist to behave.

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No, unfortunately you can't do that.

According to the wiki, the field %isplaying%, which would be needed for this is

only usable in playlist display formatting (i.e., the column title formatting patterns) http://wiki.hydrogenaud.io/index.php?title=Foobar2000:Title_Formatting_Reference#Playlist-only_fields

I did some testing and can now safely say that you can't do that, you can't even sort by a column configured to use this field

I have never used Columns UI, but it maybe it can help you

Also, in the default UI, you can still highlight the currently playing Song, using the methods described in this answer

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