Description
This Pineapple Upside Down Cheesecake Cake is surprisingly doable — make the cheesecake a day ahead, chill it overnight, then whip up the pineapple cake the next day and assemble. Easy, right?
Quick note before you start
Plan ahead: the cheesecake needs long bake + cool time, so begin the day before serving. Bold tip: make the cheesecake the day before so assembly the next day is stress-free.
Ingredients
Crust
- 1½ cups graham cracker crumbs
- 1 Tbsp granulated sugar
- 6 Tbsp melted butter (salted or unsalted)
Cheesecake filling
- 4 (8 oz) packages cream cheese, at room temperature
- 1 2/3 cups granulated sugar
- 1/4 cup cornstarch
- 1 Tbsp vanilla extract
- 2 extra-large eggs
- 3/4 cup heavy cream
Pineapple-upside-down cake & topping
- 1 (20 oz) can pineapple slices, drained
- 1/2 cup packed brown sugar
- 4 Tbsp salted butter (for the topping)
- ~7 maraschino cherries (or more for your layout)
- 5 Tbsp salted butter (for the cake batter)
- 2/3 cup granulated sugar
- 2 large (or extra-large) eggs
- 1/2 cup buttermilk
- 1 tsp baking powder
- 1 tsp vanilla extract
- 1/4 tsp salt
- 1/4 tsp baking soda
- 1 1/4 cups all-purpose flour
To serve (optional)
- Extra cherries and warmed caramel sauce
Instructions
How to make it — day-by-day plan
Day 1 — bake the cheesecake
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Preheat the oven to 350°F. Wrap a 9″ springform pan tightly in heavy-duty foil so no water leaks into it during the water bath. Bold tip: foil the pan thoroughly — don’t skip this.
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Stir the graham crumbs, sugar, and melted butter together. Press the mixture into the bottom (and, if you like, a little way up the sides) of the prepared springform. Bake 8 minutes; cool.
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In a mixer with the paddle or a large bowl and electric mixer, beat one package of cream cheese with 1/3 cup sugar and the cornstarch on low until smooth (about 3 minutes). Scrape the bowl.
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Add the remaining packages of cream cheese one at a time, beating after each addition until smooth.
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Increase speed to medium. Mix in the remaining 1 1/3 cups sugar and the vanilla until combined.
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Add eggs one at a time, mixing well after each.
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Beat in the heavy cream just until the batter looks light and creamy — don’t overmix. Overbeating can introduce air that causes cracks.
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Set the springform inside a roasting pan. Pour the cheesecake batter into the crust. Carefully pour hot water into the roasting pan until it reaches about 1″ up the outside of the springform (watch for splashes).
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Bake until the top turns very faintly golden and the center barely jiggles, about 1 hour 15 minutes. Remove from the oven, lift the springform out of the water bath, and cool on a rack for 2 hours. Cover loosely and refrigerate overnight. Bold tip: chill the cheesecake overnight for best texture and cleaner slices.
Day 2 — make the pineapple cake and finish the cake
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Preheat the oven to 350°F. Spray a 9″ round cake pan with nonstick spray.
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In a small saucepan over low heat, melt 1/2 cup brown sugar with 4 Tbsp butter just until the sugar dissolves — do not boil. Remove from heat and pour into the cake pan, tilting to coat the bottom evenly. Bold tip: stop when sugar dissolves; boiling will harden the topping later.
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Pat the pineapple slices dry with paper towels. Arrange them over the brown sugar layer and tuck cherries into centers or wherever you like for decoration.
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Melt 5 Tbsp butter in a microwave-safe bowl (about 1 minute). Whisk in 2/3 cup sugar, then beat in the eggs. Stir in the buttermilk, baking powder, vanilla, salt, and baking soda. Add the flour and fold until just combined — don’t over-stir.
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Pour the batter evenly over the fruit layer and bake about 30 minutes, or until a toothpick inserted in the center comes out clean. Cool in the pan 1 minute.
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To unmold, place a flat, rimless baking sheet or plate on top of the pan, flip to invert the cake, and remove the pan. Let the pineapple cake cool completely with the caramelized fruit facing up. Bold tip: pat the fruit dry before arranging so the topping stays glossy, not watery.
Assembly
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Remove the chilled cheesecake from the fridge and remove the springform sides; leave the cake on the springform base for stability.
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Center the cooled pineapple-upside-down cake on a flat spatula or cake lifter and gently lower it onto the cheesecake, fruit side up. Slide it into place so both layers sit flush.
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Slice and serve with warmed caramel sauce and extra cherries if desired.
Notes
- Notes, swaps & troubleshooting
- Short on time? Use 1/3–1/2 cup prepared caramel sauce in the bottom of the pan instead of melting brown sugar and butter. It’s a shortcut; IMO homemade tastes better but this saves time.
- If your caramelized sugar hardens, you cooked it too long — start fresh and melt gently on low heat.
- Fresh pineapple works wonderfully here; just slice and pat dry before placing.
- Store the assembled cake in the refrigerator. Components freeze well separately; thaw completely before assembling.
- We used maraschino cherries for the classic look, but fresh or glace cherries work fine.
- Quick tips for success
- Wrap the springform in foil to protect it during the water bath.
- Chill the cheesecake overnight for clean, stable slices.
- Avoid overmixing the cheesecake batter and the cake batter; gentle handling keeps textures tender.
- Pat pineapple dry to keep the topping from getting runny.
- Don’t boil the brown sugar mixture — just melt and combine.
- Serving suggestions
- Serve slices slightly chilled with a warm drizzle of caramel — that hot-cold contrast is addictive. Pair with a bright citrus cocktail or a scoop of vanilla ice cream if you want to go all-out.
- Final thought
- Two recipes, one big reward. Make the cheesecake ahead, relax a little, then bake the pineapple cake the day you serve. Got a helper? Great — hand off the batter stirring and claim the royal candle-blowing duties. Birthday wish, granted. 🎂