Pineapple Upside Down Inspired Cupcakes

I was challenged to a cupcake bake-off at work recently.  Another coworker and myself enjoy cooking and baking and occasionally bring in treats for everyone to enjoy.  Someone at work suggested that we go head-to-head with our baking skills, leading to this baking challenge.  We are each to bake two different flavors of mini cupcakes and bring them to work.  This is one of my flavors.  It was the favorite at home, but not the winner at work.

I have always enjoyed a good pineapple upside down cake.  Believe it or not, I'm not a big frosting fan, so it used to be my birthday cake of choice.  These cupcakes are not exactly like a pineapple upside down cake, but they definitely take their inspiration from them. I made a brown sugar frosting, but found the flavor was a littler overpowering for the cakes, so I mixed it half-and-half with a butter cream frosting.

Ingredients

Cupcake

2 cups cake flour

1 + 1/4 cup sugar
1 tablespoon bking powder
1 teaspoon salt
1/2 cup butter, softened
1 cup buttermilk
1 teaspoon vanilla extract

2 eggs, at room temperature (I put mine in a small bowl with warm water)
1 (10 oz) can crushed pineapple, drained
1 (16 oz) jar maraschino cherries, drained and dried (halved if making mini cupcakes)


Brown Sugar Frosting
1/4 cup butter
1/2 cup brown sugar, packed
1/8 cup milk
1 cup powdered sugar

Butter Cream Frosting

1/4 cup butter, softened
1 cup powdered sugar
1-2 tablespoons milk

Directions

1. Preheat oven to 350°F. Line cupcake tin with cupcake liners. I made one pan of mini cupcakes and one pan of regular sized ones.

2. In a large mixing bowl, mix cake flour, sugar, baking powder and salt.

3. Add softened butter, butter milk and vanilla. Beat with a hand mixer on medium speed for 2 minutes, occasionally scraping sides of bowl.

4. Add eggs, beat for 2 more minutes.

5. Fold in drained pineapple.

6. Pour batter into cupcake lined pans. For mini cupcakes, fill with a tablespoon. For regular cupcakes, fill with 1/4 cup. Place half of a maraschino cherry on top of mini cupcakes or a whole cherry on top of regular cupcakes. Bake 10-12 minutes for mini cupcakes and 13-15 minutes for regular cupcakes.

7. Cool in pans for 10 minutes. Remove from pans to finish cooling (at least 1 hour before frosting).

I prepare my frosting while the cupcakes are cooling.  You'll want to make the brown sugar frosting first:

1. Melt butter in saucepan.

2. Add brown sugar and bring to a boil. Lower to medium-low heat and continue boiling for 2 minutes, stirring constantly.

3. Add the milk and return to a boil, stirring constantly.

4. Remove from heat and let cool until lukewarm.

5. After cooled, add powdered sugar gradually and stir until combined. The frosting should be thick enough to stand up, but not so thick that it can't be spread.  If it's is too thin, add more powdered sugar. If it is too thick, add some hot water.

6. Prepare the butter cream frosting.  Beat the softened butter and powdered sugar together until combined. Add milk until it reaches the desired consistency.

7. Mix the two frostings until combined.  You could certainly use the brown sugar frosting or butter cream frosting on their own; just double the ingredients for whichever you are using.

8. Frost cupcakes after they have cooled completely.

The pineapple flavor on these came through wonderfully! And the frosting tastes a lot like the glaze you would find on a pineapple upside down cake.
  

The maraschino cherry!

I'll post my other flavor for you. It was the overall winner at work!