Lowlander wrote: ↑Sun Mar 15, 2020 11:48 am Start with File > Maintain Library with complete optimization checked.

I'll try it.

Also, I was able to solve it by:
a) creating a new autoplaylist with the same criteria,
b) in the existing faulty autoplaylist, changing a criteria, changing it back, then hitting OK. This must have refreshed it and now the original autoplaylist is working again.

Start with File > Maintain Library with complete optimization checked.

MM v4.1.27.1897 Portable Mode
Windows 10
iPod 5G, 160GB

I've had the same autoplaylists for years and across many versions of MM. However, I noticed that one autoplaylist is populating improperly now. It seems to be ignoring all the criteria set for it.

For example, the autplaylist "My Autoplaylist" has the following criteria:
- Match [All] of the following criteria
- Genre - contains - MyGenre
- Occasion - is - MyOccassion
- Rating - >= - 4.5 Stars

That autoplaylist is completely ignoring all the criteria (genre, occassion, rating) and including roughly 99% of the total music library. However, another autoplaylist I have works perfectly.

This is also a big problem because I can no longer sync my iPod. It has run out of room since it is trying to sync my entire library which is much bigger than the iPods capacity.