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Pineapple Upside-Down Cupcakes

Pineapple Upside-Down Cupcakes

Pineapple Upside-Down Cupcakes are a delightful tropical twist on the classic upside-down cake, featuring moist, tender cupcakes topped with caramelized pineapple rings and maraschino cherries. Enveloped in a buttery brown sugar glaze, these cupcakes offer a juicy, flavorful, and visually stunning treat perfect for any occasion, from casual gatherings to elegant celebrations.

Ingredients

Topping

  • Fresh Pineapple Rings (one per cupcake)
  • Maraschino Cherries (one per pineapple ring)
  • Brown Sugar (about 1/2 cup for glaze)
  • Unsalted Butter (about 1/4 cup for glaze)

Cake Batter

  • All-Purpose Flour (1 1/2 cups)
  • Baking Powder (1 1/2 teaspoons)
  • Salt (a pinch)
  • Eggs (2 large)
  • Granulated Sugar (3/4 cup)
  • Vanilla Extract (1 teaspoon)
  • Milk (1/2 cup)

Instructions

  1. Prepare the Topping: Melt the butter in a small saucepan and stir in the brown sugar until the mixture is smooth and bubbly. Pour an equal amount of this caramelized mixture into the bottom of each cupcake liner. Place a fresh pineapple ring on top of the glaze, then place a maraschino cherry at the center of each pineapple ring. This layer will caramelize as the cupcakes bake.
  2. Mix the Cake Batter: In a mixing bowl, whisk together the flour, baking powder, and a pinch of salt. In another bowl, beat the eggs, granulated sugar, vanilla extract, and milk until smooth. Gradually add the dry ingredients to the wet ingredients and stir gently until just combined to avoid overmixing and tough cupcakes.
  3. Assemble the Cupcakes: Spoon the batter carefully over the pineapple rings in each cupcake liner, filling each about two-thirds full. Take care to keep the topping in place so the cherries don’t move during baking.
  4. Bake: Place the cupcake pan in a preheated oven at 350°F (175°C) and bake for 18 to 22 minutes, or until a toothpick inserted in the center comes out clean. The batter will rise, and the topping will bubble into a sticky, caramelized glaze.
  5. Cool and Flip: Allow cupcakes to cool in the pan for about 10 minutes. Then, carefully invert each cupcake onto a plate or wire rack so the pineapple and cherry topping faces up, showcasing the glossy, colorful caramelized topping.

Notes

  • Use room temperature eggs, butter, and milk for the best batter consistency and texture.
  • Fill cupcake liners only two-thirds full to prevent overflow and maintain cupcake shape.
  • Fresh pineapple caramelizes better and tastes brighter than canned pineapple.
  • Let cupcakes cool 10 minutes before flipping to avoid the topping sticking.
  • Customize by adding chopped nuts or a sprinkle of cinnamon on top for extra flavor and texture.

Nutrition

Keywords: pineapple upside-down cupcakes, tropical cupcakes, caramelized pineapple, brown sugar glaze, easy cupcakes, tropical dessert