Specific song not showing on Replay playlist

I have been listening to a specific song for a really long time, but it isn't showing up on my '26 Replay playlist. I know I've listened to it more than another song that shows up on the playlist I started listening to around the same time. So I know it should be on the playlist, but it just isn't. I have Sync Library on and listening history enabled, so that isn't the problem. I'm afraid of turning off and on the sync since I don't want all my stuff deleted just to fix my issue.