Print

Homemade Pineapple Upside Down Cake Recipe

4.6 from 79 reviews

A classic homemade pineapple upside down cake featuring a caramelized brown sugar and butter glaze topped with pineapple rings and maraschino cherries. This moist and flavorful cake is topped with a cream cheese-enriched batter infused with crushed pineapple, delivering a perfect balance of sweetness and tang.

Ingredients

Scale

Pineapple Glaze

  • ¼ cup butter
  • ½ cup brown sugar
  • ½ teaspoon cinnamon
  • 24 ounce can pineapple rings
  • Maraschino cherries

Cake Batter

  • 6 tablespoons butter, softened
  • ¾ cup granulated sugar
  • ⅓ cup softened cream cheese
  • 2 eggs
  • 1 teaspoon vanilla extract
  • ¾ cup crushed pineapple, in juice
  • 1¼ cups all-purpose flour
  • ½ teaspoon baking powder
  • ½ teaspoon salt

Instructions

  1. Preheat Oven: Preheat your oven to 350°F (175°C) and line a 10-inch round cake pan with parchment paper to prevent sticking.
  2. Make Pineapple Glaze: In a saucepan, combine ¼ cup butter, ½ cup brown sugar, and ½ teaspoon cinnamon. Melt together over medium heat for about 5 minutes, stirring until sugar dissolves fully. Pour this melted mixture evenly into the prepared cake pan.
  3. Arrange Pineapple and Cherries: Lay the pineapple rings in a single layer on top of the sugar glaze. Place a maraschino cherry in the center of each pineapple ring. Set the pan aside while preparing the batter.
  4. Cream Butter, Sugar, and Cream Cheese: In a stand mixer fitted with a paddle attachment, cream together 6 tablespoons softened butter, ¾ cup granulated sugar, and ⅓ cup softened cream cheese until the mixture is light and fluffy.
  5. Add Wet Ingredients: With the mixer on low speed, beat in 2 eggs one at a time, ensuring each is incorporated before adding the next. Then add 1 teaspoon vanilla extract and ¾ cup crushed pineapple including juice, mixing until combined.
  6. Mix Dry Ingredients: In a separate medium bowl, whisk together 1¼ cups all-purpose flour, ½ teaspoon baking powder, and ½ teaspoon salt.
  7. Combine Batter: Gradually add the dry ingredients to the wet mixture, mixing slowly until just combined. Avoid overmixing to keep the cake tender.
  8. Pour Batter and Bake: Carefully pour the batter over the pineapple and cherry glaze in the cake pan, spreading evenly. Bake in the preheated oven for 30 to 40 minutes, or until a toothpick inserted into the center comes out clean.
  9. Cool and Invert: Let the cake cool for 5 minutes in the pan. Then place a serving platter over the cake pan and invert it to release the cake, revealing the caramelized pineapple and cherries on top. Serve warm or at room temperature.

Notes

  • Use a sharp knife to loosen edges before inverting the cake to avoid sticking.
  • For best results, use canned pineapple rings packed in juice rather than syrup to reduce extra sweetness.
  • The cake can be served warm or at room temperature; store leftovers covered in the refrigerator for up to 3 days.
  • You can substitute cream cheese with mascarpone for a richer flavor.
  • Ensure the butter and cream cheese are softened to room temperature for easier creaming.

Keywords: pineapple upside down cake, classic dessert, caramelized pineapple cake, homemade pineapple cake, maraschino cherries cake