Can't Play Purchased Song

I have bought a lot of songs on iTunes over the years.

However, I purchased a song a few hours ago and cannot get it to play in iTunes. Each time I try playing this new song, I receive a dialogue box saying "This computer is not authorized" and I get prompted to input my iTunes email address and password.

So I type in my email address and password and a new dialogue box says "This computer had previously been authorized, it has been re-authorized". So I try to play the song which brings the login box back up where I'm asked to input my email address and password. Wash, rinse, repeat. The song never plays!

The weird part is items purchased previously in iTunes play like normal. There are no problems with playing songs/movies/TV shows/whatever purchased before today. Only this new song is exhibiting this problem.

iTunes Version: 12.9.0.167

OS: Windows 10

Authorized Computers: One (which is the computer I'm using right now)