Pineapple Upside Down No-Bake Cheesecake
This retro-inspired dessert gives you the classic charm of a pineapple upside-down cake—without ever making a cake.
Buttery caramelized fruit meets a fluffy no-bake cheesecake filling and a graham cracker crust that flips the script.
Literally.
It’s layered upside-down, chilled until set, then flipped out of the pan for a showstopping square that tastes like summer nostalgia.
So here’s the plan. Roast the pineapple and cherries in the same caramelized sauce, and let it cool. Top it with a simple no-bake cheesecake of cream cheese, cream, powdered sugar, and vanilla. Finally, we’ll pack on the crust, and once it’s chilled, we’ll flip it over.
Skipping the cake and opting for cheesecake keeps this dessert cool and creamy, perfect for a hot summer day.
Pineapple Upside Down No-Bake Cheesecake
Fruit:
2 tablespoons salted butter
½ cup dark brown sugar
1 can pineapple slices (about 9)
12 maraschino cherries without the stems
Filling:
2 (8 oz) pkgs cream cheese, softened
2 cups powdered sugar
1 cup heavy whipping cream
1 teaspoon vanilla extract
Crust:
6 tablespoons salted butter
2 tablespoons dark brown sugar
1 cup graham cracker crumbs
Preheat the oven to 350 degrees. Line a 9-inch square pan with parchment, drop the butter in the pan, and pop it in the oven until it is melted (just a minute or two). Sprinkle the brown sugar over the top. Arrange the pineapple over the sugar, and place cherries in the gaps. Bake for 20-30 minutes until the pineapple is caramelized and softened. Allow to cool and refrigerate until chilled.
Beat the cream cheese in a stand mixer fitted with a paddle attachment until no lumps remain. Add the sugar and mix until the mixture is smooth. Add the cream and vanilla and beat until thoroughly combined. Switch to the whisk attachment and whip until the mixture is thick and fluffy. Spread it over the cooled pineapple using an offset spatula.
Mix the butter, brown sugar, and graham cracker crumbs. Spread the crust in an even layer over the filling and use the back of a measuring cup to press it into a firm layer. Chill in the fridge for at least an hour.
Place a piece of parchment or a serving platter upside down on the crust. Quickly flip the dessert over. Remove the pan and the piece of parchment. Cut into squares and serve. Store the leftovers covered in the refrigerator.