Description

This Copycat Pineapple Upside Down Cheesecake is an elegant and delicious dessert combining a creamy pineapple-flavored cheesecake with classic pineapple upside down cake layers and cherry accents. It features a rich, smooth cheesecake baked in a water bath for a perfect texture, topped with caramelized pineapple rings and maraschino cherries baked in a brown sugar and butter glaze, then layered with soft and moist pineapple cake. Ideal for special occasions or when you want a tropical twist on traditional cheesecake.

Ingredients

Scale

Pineapple Cheesecake

16 ounces cream cheese room temp
1/2 cup granulated sugar
2 large eggs
1/2 cup sour cream
2 tablespoons pineapple juice
1 teaspoon vanilla extract

Pineapple Upside-Down Cake Topping

1/2 cup unsalted butter melted
1 cup packed light brown sugar
14 slices canned or fresh pineapple rings
14 maraschino cherries

Pineapple Upside-Down Cake Batter

1 1/2 cup + 3 tablespoons all-purpose flour sifted
1/2 teaspoon baking powder
1/4 teaspoon baking soda
1/2 teaspoon salt
1/2 cup unsalted butter melted
3/4 cup light brown sugar packed
1/4 cup granulated sugar
1 large egg
1/4 cup sour cream
1/2 cup milk
1/4 cup pineapple juice
1 tablespoon vanilla extract

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Instructions

Prepare Cheesecake Batter: Preheat the oven to 325°F. Grease a 9-inch springform pan, wrap the outside in heavy-duty foil, and set aside. In a large bowl, whip the cream cheese and granulated sugar using an electric hand mixer until smooth. Mix in eggs one at a time until fully combined, scraping down the sides as needed. Add sour cream, pineapple juice, and vanilla extract and mix until completely smooth.
Bake Cheesecake: Pour the cheesecake batter into the prepared pan and place it into a larger roasting pan. Reduce oven temperature to 300°F. Fill the roasting pan with hot water halfway up the sides of the springform pan to create a water bath. Bake for 45 minutes. Then turn off the heat and leave the cheesecake in the oven for an additional 20 minutes to set. Remove from oven and water bath, cool to room temperature on the counter, then cover and refrigerate for at least 8 hours or overnight.
Prepare Upside-Down Cake Topping: Divide melted butter equally between two 9-inch cake pans. Sprinkle 1/2 cup of light brown sugar in each pan evenly. Arrange pineapple slices on top of the sugar in each pan, then place a maraschino cherry in the center of each pineapple ring. Set aside.
Make Cake Batter: Preheat oven to 350°F. In a large bowl, whisk together sifted all-purpose flour, baking powder, baking soda, and salt. In another medium bowl, whisk together melted butter, light brown sugar, and granulated sugar until smooth. Whisk in egg, sour cream, milk, pineapple juice, and vanilla extract until fully combined.
Combine and Bake Cake: Add the wet ingredients to the dry ingredients and stir until combined with no dry spots or lumps. Evenly divide the batter between the two prepared pans on top of the pineapple and cherries. Smooth the tops carefully. Bake for 30 minutes until golden brown and a toothpick inserted into the center comes out clean. Cool cakes in pans on wire racks for 10 minutes.
Assemble Cake Layers: Invert one pineapple upside-down cake layer onto a flat surface such as a cutting board. Carefully invert the second cake layer onto the serving plate so the pineapple and cherries are facing up.
Assemble Final Cheesecake: Remove the cheesecake from the springform pan carefully using an offset spatula if needed, and lift it off the pan bottom. Place the cheesecake on top of the first cake layer. Then place the second upside-down cake layer on top of the cheesecake, pineapple side up. Serve immediately or refrigerate until ready to serve. Optionally garnish with whipped cream.

Notes

Room Temperature Ingredients: Ensure cream cheese, eggs, and sour cream are at room temperature to achieve a smooth cheesecake filling.
Water Bath: Baking the cheesecake in a water bath prevents cracks and keeps the texture creamy and tender.
Proper Mixing: Mix cheesecake filling on low speed to avoid incorporating excessive air which can cause cracking.
Cool Completely: Allow cheesecake to cool to room temperature before refrigerating to help it set properly.
Invert Carefully: Gently invert the pineapple upside-down cakes to keep the pineapple rings and cherries intact and well positioned.
Chill Time: Refrigerate the assembled cheesecake for several hours or overnight for the best texture and flavor melding.

Nutrition

Serving Size: 1 slice
Calories: 450 kcal
Sugar: 35 g
Sodium: 280 mg
Fat: 28 g
Saturated Fat: 17 g
Unsaturated Fat: 9 g
Trans Fat: 0 g
Carbohydrates: 40 g
Fiber: 1 g
Protein: 6 g
Cholesterol: 120 mg