How do I update my checked-songs playlist to reflect songs i unchecked and checked in my library

I have a checked-songs playlist with 50 songs in it. It matches the rule 50 songs limit and only checked items.

Today I went in to refresh those items, so in my library I unchecked some songs and checked new ones, but the new ones were not added to my checked-songs playlist.

How do I update my checked-songs playlist to reflect songs i unchecked and checked in my library