Pineapple Upside Down Cupcakes

It's been forever since I wrote a dessert recipe.  This is mostly because I eat so much already that the last thing my waistline needs is dessert lingering around the house.  But the inspiration for this dish came when I was trying to think of a dessert to take to an outdoor summer picnic.  I wanted something that could stand up to the heat and that screamed summer.  As my mind was churning, it just came to me! Pineapple upside down cake is tropical and colorful and there's no icing! So no melting and no mess.  And honestly, I got the idea to turn them into cupcakes because I've been putting everything in cupcake pans lately.  Some of you may remember my Mini-Meatloves and I learned then that when food is cooked in a cupcake pan, it cooks faster and the results are individualized, elegant and fun at the same time.

So here's my recipe for Pineapple Upside Down Cupcakes! After I posted the pictures a while back, I've gotten a few requests for this recipe.  I hope someone out there tries it and sends me pictures! :-)

Ingredients (Makes 24 cupcakes):

Non-Stick Cooking Spray

1 Can Diced Pineapples

12 Maraschino Cherries

1 Box Golden Cake Mix

2 Sticks Butter, divided

1 cup Whole Milk, at room temperature

2 Eggs, at room temperature

4 tbsp Rum, divided (preferably a spiced rum i.e. Captain Morgan or Myers)

1 cup Light Brown Sugar

Special Tools: 2 Cupcake Pans

Directions:

Preheat oven to 350 degrees.  Spray cupcake pans with non-stick cooking spray and set aside. First prep your fruit by cutting the cherries in half to make 24 halves.  Then (depending on the brand of canned pineapple you use) halve the pineapple cubes so that they are about the same width as the cherries. 

Next prepare your cake batter.  Begin by melting and cooling 1 stick of butter.  Then in a bowl, combine the cake mix, melted butter, milk, eggs, and rum.  Mix with an electric mixer for 2-3 minutes until all ingredients are combined, being sure to scrape the sides and get any ingredients lingering at the bottom of the bowl.  Set batter to the side while you make your caramel sauce.

In a small frying pan, melt the remaining stick of butter over medium heat.  Once it’s completely melted, add the brown sugar and stir until sugar is completely combined.  Increase the heat slightly, and stir the mixture constantly until it begins to bubble.  When the mix begins to get lighter in color, almost frothy, remove the pan from the heat, add the remaining 2 tablespoons of rum, and stir to combine.

Spoon about 1 teaspoon caramel sauce into each cupcake round.  Then press a cherry in the center and 2 pineapple chunks around the cherry.  Lastly pour the cake batter evenly into the cupcake pan, trying to only fill each round ¾ of the way full (if you pour too much your tops will round and remember your tops become your bottom!)

Place the cupcakes in the oven and bake until golden brown 25-30 minutes or until a toothpick comes out clean when inserted into the center of a cupcake. Once cooked, take cupcakes out of the oven and place on a wire rack to cool for 15 minutes.  Once cooled slightly, invert cupcake pan over a large cookie sheet.  Tap the tops of each cupcake round to ensure that the cupcakes come out.  Gently lift the cupcake pan and you should be left with your upside down pineapple cupcakes on the sheet. 

Place cupcakes on a nice plate or platter and serve with vanilla ice cream.  If some fall apart, it’s ok, simply piece them back together or use the crumbles as an ice cream topping.