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Classic Cozy Old-Fashioned Pineapple Upside Down Cake

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A nostalgic and comforting pineapple upside down cake featuring caramelized brown sugar and buttery tender crumb, perfect for cozy nights and family gatherings.

Ingredients

Scale
  • 3/4 cup (150g) brown sugar (light or dark)
  • 1/4 cup (56g) unsalted butter, softened
  • 7–8 pineapple rings, fresh or canned in juice
  • 7–8 maraschino cherries (optional)
  • 1 1/2 cups (190g) all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 3/4 cup (150g) granulated sugar
  • 2 large eggs, room temperature
  • 1 teaspoon vanilla extract
  • 1/2 cup (120ml) whole milk or dairy-free substitute

Instructions

  1. Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan thoroughly with butter and set aside.
  2. In the cake pan, evenly sprinkle the brown sugar. Dot with softened butter, pressing and spreading into an even layer.
  3. Arrange pineapple rings on top of the caramel mixture, fitting as many as possible without overlapping. Place a maraschino cherry in the center of each ring if desired.
  4. In a medium bowl, whisk together flour, baking powder, and salt. Set aside.
  5. In a large bowl, cream granulated sugar and softened butter with an electric mixer or whisk until light and fluffy, about 2-3 minutes.
  6. Add eggs one at a time, beating well after each addition. Stir in vanilla extract.
  7. Alternate adding dry ingredients and milk to the butter mixture, beginning and ending with dry ingredients. Mix just until combined.
  8. Pour batter carefully over pineapple and caramel in the pan, spreading evenly with a spatula.
  9. Bake for 40-45 minutes or until a toothpick inserted in the center comes out clean and edges are golden.
  10. Cool cake on a wire rack for 10 minutes. Run a knife around edges to loosen, then invert onto a serving plate.
  11. Let cake cool slightly before slicing to allow caramel sauce to soak in.

Notes

Grease the pan thoroughly with softened butter for easy release. Cream butter and sugar until fluffy to trap air for a tender crumb. Alternate wet and dry ingredients to avoid overmixing. Let the cake rest 10 minutes before flipping to prevent sticking. Tent with foil if browning too fast.

Nutrition

Keywords: pineapple upside down cake, old-fashioned cake, caramelized pineapple, classic dessert, easy cake recipe, cozy dessert

Find it online: https://shimmersnack.com/classic-cozy-old-fashioned-pineapple-upside-down-cake-recipe-easy-and-perfect/