I’ve often noticed that if you’re in iTunes list view, track ordering is not 
automatically set to either be based on track/disc number or play order but 
often reverts to some other column, usually name for me.  Bloody annoying, 
especially since it works flawlessly on iOS and I spent a long time getting all 
the disc/track information metadata configured.

Try VO-Shift-Backslash when you’re in the songs table.  Go to the status column 
and press VO-space, to sort on that.  Leave the headers again with VO-Shift-\.  
Now you should have what iTunes thinks is the correct play order.  If it’s 
reversed, do it again to turn the list the right way up.

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