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Pineapple Upside-Down Cupcakes

Pineapple Upside-Down Cupcakes

These Pineapple Upside-Down Cupcakes combine moist, tender cake with a caramelized pineapple and cherry topping for a delightful tropical twist on the classic dessert. Perfectly portioned and easy to share, these cupcakes deliver bright, sweet, and buttery flavors with a hint of nostalgia. Ideal for weekend baking or special occasions, they are customizable, beginner-friendly, and irresistibly tasty.

Ingredients

Scale

Caramel Topping

  • 1/2 cup brown sugar
  • 1/4 cup unsalted butter
  • Pineapple rings or chunks (enough for 5 cupcakes)
  • 5 maraschino cherries

Cake Batter

  • 1 cup all-purpose flour (or gluten-free flour blend)
  • 3/4 cup granulated sugar
  • 1 1/2 tsp baking powder
  • 1/4 tsp salt
  • 1 large egg
  • 1/2 cup milk
  • 1/4 cup unsalted butter, melted
  • 1 tsp vanilla extract

Instructions

  1. Prepare the caramel topping: Melt butter and brown sugar together over medium heat until bubbling and smooth. Spoon about 1 tablespoon of the caramel mixture into each cupcake liner. Place a pineapple ring or chunk on top of the caramel in each liner, then add a maraschino cherry in the center.
  2. Mix the batter: In a bowl, whisk together the dry ingredients: flour, sugar, baking powder, and salt. In another bowl, beat the egg, then add the milk, melted butter, and vanilla extract. Gradually combine the wet ingredients with the dry, mixing gently until the batter is smooth and free of lumps.
  3. Assemble the cupcakes: Pour the batter evenly over the pineapple and caramel mixture in each cupcake liner, filling each about two-thirds full to allow room for rising.
  4. Bake until golden: Place the cupcake pan in a preheated oven at 350°F (175°C) and bake for 18-22 minutes, or until a toothpick inserted into the center comes out clean.
  5. Cool and invert: Let the cupcakes cool in the pan for about 5 minutes. Then carefully invert the cupcakes onto a wire rack to reveal the caramelized pineapple and cherry topping. Allow to cool completely before serving.

Notes

  • Use fresh pineapple for brighter flavor and better caramelization.
  • Resting the batter for 10 minutes before baking improves texture.
  • Grease cupcake liners well or use silicone liners to prevent sticking and preserve topping integrity.
  • Monitor baking time closely to avoid drying out the cupcakes.
  • Invert cupcakes while still warm for a clean release and glossy topping.

Nutrition

Keywords: pineapple upside-down, cupcakes, tropical dessert, caramelized topping, easy baking, gluten-free option, pineapple dessert