Pineapple Upside-Down Cake Cupcakes

A coworker of mine was interested in placing an order for her husband's birthday and told me he loved pineapple upside-down cake.  When she asked me if I could turn it into a cupcake, I of course said yes!  I'm always up for a challenge.  I've never eaten pineapple upside-down cake so I did some research to prepare for this challenge.  I also looked up some pineapple upside-down cupcakes, but all I found were pineapple upside-down cakes baked in a muffin pan and called "cupcakes."  Now some may beg to differ, but to me it's not a cupcake if it doesn't have frosting!  So instead of putting the pineapple on the bottom (or the top depending on how you want to look at it), I decided to fill the cupcakes with it, so I would be able to frost them.  I baked the pineapple brown sugar mixture just as you would if you were making a real pineapple upside-down cake, just minus the cake batter.  It turned out just as I had imagined it, and the flavors all work together nicely!

Pineapple Upside-Down Cake Cupcakes
Cake:
1/4 cup water
1/2 cup buttermilk
1/2 cup vegetable oil
1 1/2 tsp vanilla extract
1 cup sour cream
2 eggs
1 box Yellow Cake Mix (I used Duncan Hines)


Filling:
1/2 cup butter
1 can crushed pineapples (20 oz)

1 cup brown sugar

Frosting:
1/2 cup butter, softened
8 oz cream cheese, softened
1 1/2 tsp vanilla
1/4 cup of caramel sauce
4-5 cups powdered sugar


1.  Preheat oven to 350 degrees and line muffin tins with cupcake liners.
2.  In a large bowl, whisk together water, buttermilk, oil, sour cream, and vanilla extract.
3.  Add eggs, one at a time, whisking to combine after each addition.
4.  Slowly add the yellow cake mix while stirring.
5.  Fill cupcake liners about 3/4 full and bake for 14-18 minutes, or until toothpick inserted in center comes out clean.  Remove from pans and cool on wire racks completely.

6.  When cupcakes come out of oven, increase oven temperature to 400 degrees.  To make filling, melt 1/2 cup butter in cake pan in oven.  Remove pan from oven and stir in brown sugar.  Spread brown sugar mixture evenly on bottom of pan.  Strain crushed pineapple and spread evenly over brown sugar.  Bake for 45-60 minutes until mixture is thick and caramelized.  Set aside to cool.

7.  Using an apple corer, core out center of cupcake. 

 8.  Strain filling to remove excess butter and spoon filling into center of cupcake.

9.  To make frosting:  Beat butter and cream cheese until light and fluffy.  Add vanilla and caramel sauce, and beat until combined.  Add powdered sugar until desired consistency is reached.

10.  Pipe onto cooled cupcakes.