Sadly, this has been an on-and-off again issue for iTunes for at least 2 years (probably more but I've had it for that long). Apple seems not to care since it's never been addressed or corrected.
It also is a bit random - sometimes it updates in full, sometimes only a few songs played update and others nothing's updated. It doesn't even tie to purchase-type since you get both iTunes purchased songs both updating and not as well as CD burned songs or songs imported from another source.
And, as I noted, since Apple in no way seems to care.. easily seen if you search and see the vast number of threads on this over the years without Apple response, it'll keep on happening.