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Pineapple Upside Down Cake

A nostalgic dessert featuring caramelized pineapple and cherries atop a moist, buttery cake. Perfect for special occasions or everyday treats.
Prep Time 20 minutes
Cook Time 50 minutes
Total Time 1 hour 10 minutes
Course Breakfast, Dessert
Cuisine American
Servings 8 servings
Calories 350 kcal

Ingredients
  

For the topping

  • ½ cup brown sugar (packed) Essential for the gooey caramel topping.
  • ¼ cup salted butter (melted) Can use unsalted but add a pinch of salt.
  • 1 can (20-ounce) sliced pineapple (drained, juice reserved) Choose pineapple in juice, not syrup.
  • 12 pieces maraschino cherries Provides color and nostalgia.

For the cake

  • 1 ⅓ cups all-purpose flour Can use a gluten-free blend if needed.
  • 1 teaspoon baking powder Check for freshness for best results.
  • ½ teaspoon salt Enhances sweetness.
  • ¼ cup unsalted butter (softened) Should cream well with sugars.
  • ½ cup granulated sugar Adds straightforward sweetness.
  • ¼ cup brown sugar (packed) Incorporated into the cake batter.
  • 1 large egg (room temperature) Room temperature helps better emulsification.
  • ¼ cup sour cream Adds richness and moisture.
  • ¼ cup milk Keeps the cake tender.
  • ¼ cup pineapple juice (from reserved juice) Adds fruity moisture to the cake.

Instructions
 

Preparation

  • Preheat your oven to 350°F (175°C) and spray a 9-inch cake pan with pan spray.
  • In a small bowl, mix together ½ cup brown sugar and ¼ cup melted salted butter; spread this into the bottom of the cake pan.
  • Press pineapple slices between paper towels to remove excess moisture. Arrange them in the pan with cherries nestled among them.

Mixing

  • In a small bowl, whisk flour, baking powder, and salt together.
  • In a large bowl, beat softened unsalted butter with granulated and brown sugars until light and fluffy.
  • Add the egg, sour cream, milk, and ¼ cup of reserved pineapple juice, mixing until just combined.
  • Gradually fold in the dry ingredients until just combined—be careful not to overmix.

Baking

  • Spread the batter evenly over the arranged pineapple and cherries.
  • Bake for 45-50 minutes or until golden brown and a toothpick inserted in the center comes out clean.
  • Cool for 10-15 minutes before inverting onto a plate or cake stand.

Notes

Consider serving with whipped cream or vanilla ice cream. For added texture, sprinkle with toasted coconut or chopped nuts. Store leftovers covered at room temperature for up to three days.
Keyword Dessert Recipe, Family Recipe, Nostalgic Cake, Pineapple Cake, Upside Down Cake