Pineapple Upside Down Cheesecake
Indulge in a delicious pineapple upside down cheesecake that's perfect for any occasion. It's moist, sweet and fruity - a wonderful choice.
Servings: 8
Equipment
- Roasting Pan Large
- 2 Cake Pans 9-Inch
- Stand Mixer with Paddle or Roller Attachment
Ingredients
For the Cheesecake Filling:
- 16 Ounces cream cheese at room temperature
- ⅔ Cup granulated sugar
- 2 eggs
- ⅓ Cup sour cream
- ⅓ Cup heavy cream
- 1 Tablespoon pineapple juice from the can
- 2 Teaspoons maraschino cherry juice from the jar
For the Cake Batter:
- 1½ Cups all-purpose flour
- ½ Teaspoon baking powder
- ¼ Teaspoon baking soda
- ½ Teaspoon salt
- ½ Cup butter 1 Stick at room temperature
- 1 Cup granulated sugar
- 1 egg at room temperature
- 2 Teaspoons vanilla extract
- ¼ Cup pineapple juice reserved from the sliced pineapple, plus water if necessary to fill to ¼ Cup
- ½ Cup whole milk
Additional Ingredients:
- ½ Cup butter melted
- ⅔ Cup light brown sugar
- 1 Teaspoon ground cinnamon
- 14 maraschino cherries stems removed
- 2 Cans sliced pineapple 20-Ounce Cans, drained (you need a total of 14 slices for the cake)
- nonstick cooking spray as needed
Instructions
Make the Cheesecake Layer:
- Preheat the oven to 325°F and put a large roasting pan in the lower ⅓ of the oven. Fill the pan with a gallon of warm or hot water.
- Put the second oven rack in the middle of the oven.
- Grease with shortening or spray a 9-inch springform pan well with nonstick spray and line the bottom with parchment paper.
- In a large mixing bowl of a stand mixer, combine the cream cheese and sugar fitted with the paddle/roller attachment until smooth, scraping down the sides as necessary.
- Add the eggs one at a time, blending each into the cream cheese.
- Add the sour cream, heavy cream and pineapple juice. Mix until smooth and combined.
- Pour the cheesecake batter into the prepared springform pan.
- Pour the maraschino cherry juice into a circle in the center of the batter and swirl using the dull end of a butter knife.
- Put the springform pan on the oven rack above the water-filled large roasting pan.
Bake the Cheesecake Layer:
- Bake for 55 to 60 minutes or until the cheesecake is set to the touch and not jiggling.
- Remove it from the oven and cool it for 1 hour.
- Remove the collar from the springform pan and put the cheesecake in the freezer for at least 3 hours while you make the cake.
Make the Cake Layers:
- Turn up the oven to 350°F.
- Grease and flour a pair of 9-inch cake pans and set aside. Use bake even fabric wrap strips around the cakes to ensure even, flat baking - soak them in a bowl of warm water while you prepare the cake batter.
- In a mixing bowl, mix the flour, baking powder, baking soda, and salt together.
- In a large mixing bowl, add the butter and sugar and with a handheld electric mixer beat on a high speed until the texture is sandy and color is pale yellow.
- Add the egg and blend to combine.
- Add the vanilla and pineapple juice and mix until combined.
- Add half the flour mixture to the egg mixture and mix on low until combined.
- Add all the milk and mix again.
- Finally, add the rest of the flour mixture and mix until combined.
- Set the cake batter aside while you prepare the cake pans.
Prepare the Cake Pans:
- Remove the fabric cake slings from the water, gently wringing out some water (not all of it).
- Fit them around the prepared cake pans and set aside.
- In a small bowl, mix the brown sugar and cinnamon together.
- Divide the melted butter between the bottom of 2 x 9-inch round cake pans, then divide the brown sugar cinnamon mixture into each pan on top of the melted butter.
- Arrange the slices of pineapple in each cake pan and add a cherry in the center of each pineapple slice.
- Divide the batter evenly between the 2 pans and smooth out the top.
Bake the Cake Layers:
- Bake on the center rack for 28 to 30 minutes, until a toothpick inserted in the center comes out clean.
- Remove the cakes from the oven and let them cool for 10 minutes.
- Invert the first cake onto a plate or cake stand with the pineapple/cherry topping facing up.
- Invert the second cake onto parchment paper on a baking tray.
- Allow to cool at room temperature, then wrap and refrigerate until cold. Note: It’s possible 1 or 2 pineapple slices will not release when inverted out of the cake pan - this happens. But it's easily placed back to its space while warm as the brown sugar will provide caramelization to hold the toppings while it cools.
Assemble the Cake:
- Remove the cheesecake from the springform pan plate and put it on top of the cake on the cake stand.
- Carefully top the cheesecake with the second cake, with the pineapple/cherry design facing up. Tip: Now that the second pineapple cake is cooled, use parchment paper to flip the cake over onto a board which then allows it to be flipped onto the cheesecake layer.
- Refrigerate until you are ready to serve.
- Garnish with homemade whipped cream or dust with powdered sugar, then slice and serve.
Notes
Don't let the layers sink or shift: Ensure all layers are fully cooled or chilled before assembling.
Cutting neat slices: Cut slowly with a back and forth motion to prevent the middle layer squishing out.
Great garnishes: Fresh whipped cream with a cherry on top or maybe dusting with some powdered sugar are both good garnish options.
Cutting neat slices: Cut slowly with a back and forth motion to prevent the middle layer squishing out.
Great garnishes: Fresh whipped cream with a cherry on top or maybe dusting with some powdered sugar are both good garnish options.
Nutrition
Calories: 726kcal | Carbohydrates: 111g | Protein: 11g | Fat: 29g | Saturated Fat: 16g | Polyunsaturated Fat: 2g | Monounsaturated Fat: 7g | Trans Fat: 0.01g | Cholesterol: 141mg | Sodium: 459mg | Potassium: 425mg | Fiber: 3g | Sugar: 89g | Vitamin A: 1206IU | Vitamin C: 14mg | Calcium: 199mg | Iron: 2mg
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