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Perfect Pineapple Upside Down Cake Recipe Easy Homemade Caramelized Pineapple Dessert

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A quick and easy pineapple upside down cake featuring caramelized fresh pineapple rings and a moist, tender crumb with hints of vanilla and cinnamon. Perfect for gatherings or a comforting dessert with a tropical twist.

Ingredients

Scale
  • 4 tablespoons unsalted butter (softened, for caramel base)
  • 3/4 cup packed brown sugar (preferably dark brown sugar)
  • 1 medium fresh pineapple, peeled and sliced into rings (can substitute canned pineapple)
  • Maraschino cherries (optional, for garnish)
  • 1 1/2 cups all-purpose flour (about 190 grams)
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 3/4 cup granulated sugar
  • 1/2 cup (1 stick) unsalted butter, softened
  • 2 large eggs (room temperature)
  • 1/2 cup whole milk (120 ml, can substitute plant-based milk)
  • 1 teaspoon vanilla extract
  • 1/2 teaspoon ground cinnamon (optional)

Instructions

  1. Preheat oven to 350°F (175°C). In your cake pan or skillet, melt 4 tablespoons of butter over medium heat.
  2. Stir in the brown sugar until it dissolves and the mixture bubbles gently, about 3-5 minutes, forming a rich caramel.
  3. Arrange pineapple rings over the caramel in a single layer. Optionally, place maraschino cherries in the center of each ring. Set aside.
  4. In a medium bowl, whisk together flour, baking powder, salt, and cinnamon (if using).
  5. In a large bowl, beat softened butter with granulated sugar until light and fluffy, about 3-4 minutes.
  6. Beat in eggs one at a time, mixing well after each addition, then stir in vanilla extract.
  7. Alternately add dry ingredients and milk to the butter mixture, starting and ending with dry ingredients. Mix just until combined.
  8. Pour batter evenly over the pineapple layer in the pan.
  9. Bake for 40-45 minutes or until a toothpick inserted in the center comes out clean and the top is golden and springy.
  10. Cool cake in the pan for about 10 minutes. Run a knife around edges to loosen, then carefully invert onto a serving plate.
  11. Serve warm or at room temperature, optionally with vanilla ice cream or whipped cream.

Notes

Use fresh pineapple for best caramelization and brightness; pat dry pineapple rings to avoid soggy bottom. Avoid overmixing batter to keep cake tender. Cool cake about 10 minutes before inverting to prevent sticking. Cast iron skillet preferred for even caramelization. For gluten-free, substitute flour with 1:1 gluten-free blend; for dairy-free, use plant-based milk and butter substitutes.

Nutrition

Keywords: pineapple upside down cake, caramelized pineapple, easy dessert, homemade cake, tropical dessert, quick cake recipe

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