Purchased an entire season of a show, but newest episodes are requesting payment of $2.99
Submit a Help request thru the iTunes store.  This happened to me for Archer Season 4, Episode 4.  Took about 3-4 days, and then I finally got the email saying it was ready for me to download.  Didn't happen to any of the other shows I buy.

Not sure if the Help ticket helped, but it didn't hurt...