Ingredients

1/2 cup unsalted butter, melted

1 cup packed light brown sugar

1 can (20 oz) pineapple slices in juice, drained

10 maraschino cherries

2 (8 oz) blocks cream cheese, softened

1/2 cup granulated sugar

2 large eggs

1 teaspoon vanilla extract

1/2 cup sour cream

2 tablespoons all-purpose flour

1 box (15.25 oz) yellow cake mix (plus ingredients called for on the box)

Instructions

Step 1: Preheat the oven to 325°F (163°C). Spray a 9-inch springform pan with nonstick spray and wrap the bottom with aluminum foil to prevent leaks.

Step 2: Pour the melted butter into the bottom of the pan, then evenly sprinkle the brown sugar over it. Arrange the pineapple slices on top of the sugar and place a maraschino cherry in the center of each slice.

Step 3: In a medium bowl, beat the softened cream cheese until smooth. Add the granulated sugar and continue beating until fluffy.

Step 4: Mix in the eggs one at a time, then add the vanilla extract, sour cream, and all-purpose flour. Blend well.

Step 5: Gently pour the cheesecake mixture over the pineapple layer in the pan, spreading it evenly.

Step 6: Bake for 40–45 minutes, or until the center is just set. Remove from oven and allow to cool completely. Refrigerate for at least 4 hours or overnight to firm up the cheesecake layer.

Step 7: While the cheesecake chills, prepare the yellow cake batter according to the package instructions in a separate bowl.

Step 8: Preheat the oven to 350°F (175°C). Carefully remove the cheesecake from the springform pan and place it pineapple-side down into a greased 9-inch round cake pan.

Step 9: Pour the prepared yellow cake batter evenly over the cheesecake layer.

Step 10: Bake for 35–40 minutes or until a toothpick inserted in the center comes out clean.

Step 11: Cool the cake in the pan for 15 minutes, then invert onto a serving plate. Let cool completely before slicing and serving.

Tips & Variations

Use fresh pineapple slices for a fresher taste, but make sure to pat them dry to avoid excess moisture.

Swap maraschino cherries with fresh or glazed cherries for a less sweet topping.

For a richer cheesecake, add a splash of lemon juice or zest to the cream cheese mixture.

To prevent cracks in the cheesecake, avoid overmixing and do not open the oven during baking.

FAQs

Can I make this cake ahead of time?

Yes, this cake benefits from being made ahead since the cheesecake layer needs time to chill and firm up. You can prepare it a day in advance and refrigerate until ready to assemble and bake the final cake layer.

What type of pan should I use for this recipe?

A 9-inch springform pan is ideal for assembling the pineapple and cheesecake layers because it allows easy removal without disturbing the layers. For the final cake, a greased 9-inch round cake pan works best.