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Pineapple Upside Down Cake

This classic pineapple upside down cake features a caramelized sugar base topped with juicy pineapple rings, baked into a tender, moist crumb. The process involves caramelizing the sugar and butter directly in the skillet, then flipping the cake onto a plate to reveal a shiny, golden topping with vibrant pineapple slices. The final texture is soft and buttery with a glossy, caramelized finish that’s visually stunning.
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Prep Time 20 minutes
Cook Time 40 minutes
Total Time 1 hour
Servings: 8
Course: Main Course
Cuisine: American
Calories: 350
Ingredients Equipment Method Notes

Ingredients
  

  • 1/2 cup dark brown sugar for caramel
  • 1/4 cup unsalted butter plus extra for greasing
  • 1 can pineapple rings preferably fresh or high-quality canned
  • 1 1/2 cups all-purpose flour sifted
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 3 large eggs fresh and at room temperature
  • 1 teaspoon vanilla extract
  • 1/2 cup milk whole or 2%

Equipment

  • Skillet or ovenproof frying pan
  • Mixing bowl
  • Whisk
  • Measuring cups and spoons
  • Cake pan or ovenproof dish

Method
 

  1. Start by preheating your oven to 350°F (175°C). Grease your cake pan or ovenproof dish with a little butter to prevent sticking.
  2. In a skillet or ovenproof pan, melt the butter over medium heat. Once melted and bubbling, sprinkle the dark brown sugar evenly over the butter. Stir gently until the mixture is smooth and starts to bubble, releasing a sweet, caramel smell.
  3. Arrange the pineapple rings over the caramel, placing them in a single layer and spacing them evenly. Let them cook in the caramel for a minute or two until they start to soften and absorb the caramel aroma.
  4. In a mixing bowl, whisk together the eggs, vanilla extract, and milk until well combined and slightly frothy.
  5. In another bowl, sift together the flour, baking powder, and salt. Gradually add this to the wet ingredients, folding gently until just combined, creating a smooth batter.
  6. Pour the batter evenly over the pineapple and caramel in the skillet, spreading gently to cover all the pineapple slices.
  7. Place the skillet in the preheated oven and bake for about 35-40 minutes. The cake is done when a toothpick inserted into the center comes out clean and the top is golden.
  8. Remove the skillet from the oven and let it sit for 5 minutes. Carefully run a knife around the edges to loosen the cake.
  9. Place a serving plate over the skillet and quickly invert the cake, flipping it onto the plate. The caramelized pineapple should now be on top, shiny and golden.
  10. Gently lift the skillet away, revealing the beautiful caramel pineapple topping. Let the cake cool slightly before slicing and serving.

Notes

For an extra touch, garnish with maraschino cherries or toasted coconut flakes before serving. Ensure the caramel is not overcooked to prevent bitterness, and allow the cake to cool slightly for cleaner slices.