Mini Pineapple Upside Down Cakes


Is it opposites day? Because we are baking cakes backwards and flipping them upside down, and doing all kinds of crazy stuff. But more on that later. You know how some things are too sweet in a good way? Like puppies nuzzling babies, a full night’s sleep when you have a child, or an 80 degree day in Michigan in April (wishful thinking)? Well, these little cakes are right up there with all that good stuff.


I like a good old-fashioned dessert as much as any nostalgic foodie, however, I love a fun twist. And anything miniature. Pineapple Upside Down Cake (named because you flip it over after baking, so no, it is not opposites day – sorry!) is yellow cake doused with caramel sauce and dotted with pineapple pieces and maraschino cherries. It leads you to beg questions such as why isn’t everything doused with caramel sauce? Or is there any better way to pretend to eat fruit?

Sugar sauce and pineapple

Batter ready for the oven

These mini versions of the original are really just a safety mechanism to ensure everyone gets a cherry. Take a deep breath; you will get a cherry. Glossy and sparkly, perfectly sized and sweet, they are sure to brighten even sunny afternoons a notch more.


Mini Pineapple Upside Down Cakes


for the topping

  • a few rings from a can of pineapple, diced, or 1/2 a medium pineapple – purchase fresh at the grocery in a plastic container cored and sliced, if possible, and dice
  • 6 tablespoons unsalted butter
  • 3/4 cup packed brown sugar

for the batter

  • 1 1/2 cups flour
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 6 tablespoons unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla
  • 1/2 cup pineapple juice (use from the can or what is in the bottom of the plastic container)

How To:

Preheat oven to 350° degrees. Grease 2 cupcake pans with non-stick spray.

Melt the butter in a heavy-bottomed medium pot. Add the brown sugar and stir over medium heat for 2 minutes. Remove from heat. Drop 2 to 3 teaspoons of sugar mixture into each cupcake section, making sure the bottom is just covered. Place a few pieces pineapple and one cherry in each section on top of caramel. Set aside.

In a small bowl, sift together flour, baking powder and salt. In a large bowl, beat the butter with an electric mixer. Gradually add the sugar and beat until light and fluffy. Add in eggs one at a time, beating well after each addition. Add vanilla and mix until combined. Add half of the flour mixture and beat on low until blended. Do not overbeat. Add in pineapple juice, then remaining flour and mix until just blended. Divide into cupcake pans on top of sugar mixture. It is easiest to use a tablespoon and go sparingly first, to make sure you have enough to go around. You may come up 2 or 3 cupcakes short.

Bake for 20 minutes or until a cake tester comes out clean. Let cakes stand in pans 3 minutes before inverting onto a large platter or cookie sheet. Serve warm or at room temperature.

Save any remaining cakes in the refrigerator but bring to room temperature before serving.