Step 1

Preheat oven to 350F and lightly spray a 12-count cupcake tin with baking spray.

Step 2

Evenly divide butter into the bottom of each cupcake well.

Step 3

Sprinkle each well with 1 Tablespoon of brown sugar.

Step 4

Rim the bottom of each pan by laying 4 pineapple chunks in a flower pattern over the butter and brown sugar.

Step 5

Press a Maraschino cherry into the center of each "flower". Set aside.

Step 6

Prepare your cupcakes by beating together butter and sugar in a medium-sized bowl until creamy and well-combined.

Step 7

Add eggs, beating one at a time until combined.

Step 8

Stir in vanilla extract.

Step 9

In a separate bowl, whisk together flour, baking powder, and salt.

Step 10

Alternate adding flour and buttermilk, starting and ending with flour and mixing until just combined after each addition (I prefer to do this part by hand with a spatula to be sure not to over-mix).

Step 11

Evenly divide the cupcake batter into your prepared pan. The batter will be thick, so use a spoon to spread it evenly into each cupcake well. Fill each cupcake well all the way to the top.

Step 12

Bake on 350F for 22-25 minutes.

Step 13

Remove, allow to cool for 5 minutes, and then place a wire cooling rack over the cupcake tin, covering each cupcake.

Step 14

Carefully, using potholders as the tin will be very hot, keep the cooling rack pressed against the tin and invert. Lift the muffin tin, the cupcakes should release easily.

Step 15

Allow to cool before serving. These pineapple upside down cupcakes taste great served warm with vanilla ice cream!