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Cheesecake Filled Pineapple Upside Down Cake

This delightful dessert combines the sweet, caramel-y goodness of a traditional upside-down cake with the creamy, rich flavors of cheesecake. Perfect for summer gatherings!
Print Recipe
Prep Time 30 minutes
Cook Time 45 minutes
Total Time 1 hour 15 minutes
Servings: 8 servings
Course: Cake, Dessert
Cuisine: American, Tropical
Calories: 350
Ingredients Method Notes

Ingredients
  

For the Topping
  • 1/4 cup unsalted butter melted
  • 3/4 cup brown sugar packed
  • 1 can pineapple rings 20 oz, in juice
  • Maraschino cherries optional, for garnish
For the Cake
  • 1 1/2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1 cup sour cream
For the Cheesecake Filling
  • 8 oz cream cheese softened
  • 1/2 cup granulated sugar
  • 1 teaspoon vanilla extract
  • 1 large egg

Method
 

Preparation
  1. Preheat your oven to 350°F (175°C) and grease a 9-inch round cake pan or a springform pan.
  2. In a small saucepan, melt 1/4 cup of butter over medium heat. Stir in the brown sugar until smooth and pour this mixture into the bottom of your prepared cake pan. Arrange the pineapple rings on top and place a cherry in the center of each ring.
Mixing Cake Batter
  1. In a mixing bowl, whisk together the flour, baking powder, baking soda, and salt.
  2. In another large bowl, cream the softened butter and granulated sugar together until light and fluffy. Beat in the eggs, one at a time, followed by the vanilla extract and sour cream. Gradually add the flour mixture until just combined.
Prepare Cheesecake Filling
  1. In a separate bowl, beat together the cream cheese, sugar, vanilla, and egg until smooth and creamy.
Assembling the Cake
  1. Pour half of the cake batter over the pineapple layer. Gently spread the cheesecake filling over this layer, then top with the remaining cake batter.
Baking
  1. Bake for 40-45 minutes, or until a toothpick inserted into the center comes out clean.
Cooling and Serving
  1. Once baked, let the cake cool in the pan for about 10 minutes before inverting it onto a serving plate. Carefully remove the pan and serve.
  2. Slice it up and serve with whipped cream if desired.

Notes

Make it your own by adding coconut milk to the batter for a tropical twist. Chill the cheesecake filling for about 30 minutes to set it properly. Store leftovers in an airtight container in the fridge for up to 3-4 days.