Pretty sure this is an intended MS "feature" which just doesn't work! Lots of workarounds have been suggested elsewhere in these fora - but I think you'll find that none work satisfactorily.
I have a workaround which does work! - install AIMP2
- get ripping, converting, recording anything which goes thru your sound card (eg radio), nice skins, works with any Winamp plugins - and its free.
Not as integrated as WMP but a good substitute while they "fix" their feature.
I suggest you send feedback to MS too (Feedback tool