Recently Played Not Always Catching

[tinka]

So I have History enabled and there are no tracking control restrictions.
I have Recently Played enabled with no tracking control restrictions.

When I go to History in my Media Library, everything is fine. All plays are listed there. But when I go to Recently Played or just sort by Recently Played in Audio or Local Library... days or weeks of plays are randomly missing. Is this a known thing? Is there a setting I'm not seeing?

Thanks