Pineapple Upside Down Cupcakes

We have a birthday party for a co-worker of mine today. She loves Pineapple Upside Down Cake, and I volunteered to bake. Well, you know me, can’t do anything NORMAL, so I thought, "how can I make this unique?" The idea of a cupcake came to me, and I found quite a few recipes. I chose this one and it’s YUMMMMY! I’m planning to serve these chilled (because making them fresh isn’t an option), with Blue Bell homemade vanilla ice cream.

This makes 9 full cupcakes, or 12 small ones.

Ingredients for topping:
1 can pineapple rings
Maraschino Cherries
2/3 cup light brown sugar
1/3 cup butter, melted

Ingredients for batter:
1 cup flour
1/2 cup sugar
1/2 teaspoon cinnamon
1-1/2 teaspoons baking powder
1/2 stick butter
1/4 cup pineapple juice
1/4 cup milk
1/2 tsp vanilla
1 egg

Preheat oven to 350 degrees. Grease a non-stick cupcake pan. You won’t need cupcake liners, obviously, because you’ll be inverting these.

Melt butter and brown sugar in a small pot over the stove. Place a large table spoon of this mixture in the bottom of each cupcake cup. Placed pineapples and cherries on top of the sauce. I sliced my pineapple rings into four quarters. Two quarters fit nicely in the bottom of the cup.


In a mixing bowl, mix the flour, sugar, cinnamon and baking powder on low, with an electric mixer. Carefully add in the melted butter, pineapple juice and milk. Then add the egg and the vanilla.

Spoon the batter over the fruit and sugar into each muffin cup, evenly. Bake in the oven for 25-30 minutes, until a toothpick tester comes out clean. (Note: The sugar butter mixture bubbles up from the bottom and made quite a lovely mess in the bottom of my oven (yeah). Next time I’ll lay foil down first!)

When you take them out of the oven, let them rest in the pan for a few minutes making sure the edges are unstuck. Then place a wire rack on TOP of the pan, flipping it over and hopefully…your little cakes will just plop on out, with the pineapple on top. If not, gently tap the bottoms of the cupcake pan with a spoon. You can hear the difference in tone when the cake has released (Steven discovered this). Oh, and be sure to lay wax paper down before flipping these, because they do drip a little.


Aren’t you dying to try one? Marin whined and whined to have one. I KNEW she wouldn’t eat it, but I finally gave in. She grinned, poked it and then pushed it to the side of her highchair tray (typical Marin). She doesn’t appreciated food the way Steven and I do. Aren’t these cupcakes fun?