Mini Pineapple Upside-Down Cakes

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Ingredients

For the cake:

  • 4 large eggs, at room temperature
  • 1 and 1/4 cups granulated sugar
  • 1/4 cup dark brown sugar, packed
  • 1/2 cup pineapple juice
  • 2 teaspoons rum (or pure vanilla extract)
  • 1 and 1/2 cups all purpose flour
  • 2 and 1/4 teaspoons baking powder
  • 1/2 teaspoon cinnamon
  • 1/4 teaspoon salt
  • 2 tablespoons cornstarch

For the topping:

  • 6 tablespoons unsalted butter
  • 1 and 1/2 cups dark brown sugar (packed)
  • 1 teaspoon rum (or vanilla extract)
  • 1/8 teaspoon salt
  • 12 pineapple rings
  • 12 maraschino cherries

Instructions

  • Preheat oven to 350 degrees (F). Generously spray a 12-mold JUMBO muffin tin with non-stick cooking spray; set aside.
  • Crack the eggs into a large mixing bowl; whisk smooth. Add in the granulated sugar, brown sugar, and rum (or vanilla), and beat smooth. Stir in pineapple juice and set aside. In a separate bowl, sift together the flour, baking powder, cinnamon, salt, and cornstarch. Gradually add the dry ingredients into the wet ingredients and whisk until just combined. Be sure not to over mix here! Set mixture aside while you make the topping.

For the topping:

  • In a small sauce pan, melt the butter over medium heat. Add in the brown sugar, rum, and salt, and cook for 1 minute, whisking constantly. Remove from heat.
  • Spoon 2 tablespoons of the topping mixture into the bottom of each muffin tin; place a pineapple ring on top, then place a cherry in the middle of each pineapple ring. Divide the cake batter evenly among the prepared tins, fill each muffin tin 3/4 of the way full. Bake for 20-22 minutes, or until the tops are puffed and golden brown, and a toothpick inserted in the center of the cake comes out clean.
  • Remove from the oven and cool in pan for 5 minutes. Gently run a knife around the edge of each cake to help loosen any stuck bits, then gently place a wire cooling rack on top and quickly flip over. You may want to place the cooling rack on a large sheet pan before doing this, to help make it less messy. Serve cakes warm or at room temperature.

NOTES

Rum may be substituted with pure vanilla extract. Cakes are best eaten the day they are made, but may be stored in the fridge, in an airtight container, or on a plate covered tightly with plastic wrap, for up to 3 days.
First things first: to make this recipe you’re going to need a jumbo muffin tin. The pineapple slices won’t fit in a regular muffin tin, and while you could cut them up into tiny pieces, I highly suggest springing for the pan and following the recipe as written. Plus, once you buy a jumbo muffin tin you can make other great recipes
  1. Preheat the oven: Preheat your oven to 350 degrees Fahrenheit (175 degrees Celsius). Generously spray a 12-mold jumbo muffin tin with non-stick cooking spray and set it aside.
  2. Prepare the cake batter: In a large mixing bowl, whisk together the eggs until smooth. Add the granulated sugar, brown sugar, and rum (or vanilla extract), and beat until well combined. Stir in the pineapple juice. In a separate bowl, sift together the flour, baking powder, cinnamon, salt, and cornstarch. Gradually add the dry ingredients to the wet ingredients, whisking until just combined. Be careful not to overmix. Set the batter aside while you prepare the topping.
  3. Make the topping: In a small saucepan, melt the butter over medium heat. Add the dark brown sugar, rum, and salt, and cook for 1 minute, whisking constantly. Remove the mixture from the heat.
  4. Assemble the cupcakes: Spoon 2 tablespoons of the topping mixture into the bottom of each muffin tin. Place a pineapple ring on top of the topping in each tin, then place a maraschino cherry in the center of each pineapple ring.
  5. Bake the cupcakes: Divide the cake batter evenly among the prepared muffin tins, filling each about 3/4 of the way full. Bake for 20-22 minutes, or until the tops are puffed and golden brown, and a toothpick inserted into the center of a cupcake comes out clean.
  6. Cool and serve: Remove the cupcakes from the oven and allow them to cool in the pan for 5 minutes. Gently run a knife around the edge of each cupcake to loosen any stuck bits, then carefully place a wire cooling rack on top and quickly flip over. You may want to place the cooling rack on a large sheet pan before flipping to minimize mess. Serve the cupcakes warm or at room temperature.

Notes:

  • You can substitute rum with pure vanilla extract if desired.
  • These cupcakes are best enjoyed on the day they are made, but can be stored in the fridge in an airtight container or on a plate covered tightly with plastic wrap for up to 3 days.

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