Pineapple Upside-Down Cheesecake

By Sprig Originals ✓ · cooked up in Sprig

A tall, dense New York-style cheesecake wearing a thin buttery pineapple upside-down cake as a hat. The trick that makes this restaurant-dessert-plate showpiece actually work at home: the brown-sugar caramel and pineapple rings are baked in a separate cake pan and inverted onto the chilled cheesecake only at the end, so the crust stays crisp and the caramel stays glossy instead of bleeding into the filling. Plan on baking a day ahead — the cheesecake needs a long, cold rest.

Ingredients

• 1 1/2 cups graham cracker crumbs (about 11 full sheets)
• 2 tbsp granulated sugar
• 1/4 tsp kosher salt
• 6 tbsp unsalted butter, melted

• 32 oz full-fat block cream cheese, room temperature
• 1 1/4 cups granulated sugar
• 2 tbsp all-purpose flour
• 1/2 tsp kosher salt
• 2/3 cup sour cream, room temperature
• 4 large eggs, room temperature
• 2 tsp vanilla extract
• 2 tbsp dark rum (or 1 tbsp pineapple juice)
• 1 tsp finely grated lime zest

• 1 20-oz can pineapple rings in juice (8-10 rings), drained, juice reserved
• 9 maraschino cherries, stemmed, patted very dry
• 4 tbsp unsalted butter (for the caramel)
• 1/2 cup packed dark brown sugar
• 1/8 tsp kosher salt
• 1 cup all-purpose flour
• 1 tsp baking powder
• 1/4 tsp kosher salt
• 6 tbsp unsalted butter, softened (for the batter)
• 1/2 cup granulated sugar
• 1 large egg, room temperature
• 1/2 tsp vanilla extract
• 1/3 cup reserved pineapple juice

• 3/4 cup reserved pineapple juice
• 2 tbsp packed dark brown sugar
• 1 tbsp unsalted butter
• 1 pinch kosher salt

Instructions

1. Heat the oven to 350°F. Wrap the outside bottom and sides of a 9-inch springform pan in two layers of heavy-duty foil, sealing tightly. Stir the graham crumbs, 2 tbsp sugar, 1/4 tsp salt, and 6 tbsp melted butter until the crumbs look like wet sand, then press firmly into the bottom and 1/2 inch up the sides using a flat-bottomed glass. Bake 10 minutes, then cool on a rack. Reduce the oven to 325°F.
2. Drain the pineapple rings in a colander for at least 20 minutes, then blot both sides dry on paper towels and refrigerate until needed. Reserve all the juice (you need about 1 cup total for the batter and glaze).
3. Make the filling: beat the cream cheese with a paddle attachment (or hand mixer) on medium-low for 2 minutes until completely smooth, scraping the bowl twice. Add the 1 1/4 cups sugar, flour, and 1/2 tsp salt and beat 1 minute more. Beat in the sour cream, vanilla, rum, and lime zest.
4. Add the 4 eggs one at a time on the lowest speed, mixing just until each disappears — about 15 seconds each. Stop mixing the moment the last egg is incorporated; overbeating whips in air that causes cracks. Scrape the batter into the cooled crust and smooth the top.
5. Set the springform in a roasting pan and pour boiling water into the roasting pan to come 1 inch up the sides. Bake at 325°F for 70 to 80 minutes, until the outer 2 inches are set and the center 3 inches still jiggle as one soft unit (center reads 150°F). Turn the oven off, prop the door open with a wooden spoon, and let the cake sit 45 minutes.
6. Lift the pan from the water bath, remove the foil, and cool to room temperature on a rack, about 2 hours. Cover loosely and refrigerate at least 6 hours, ideally overnight. Do not unmold yet.
7. Bake the pineapple layer (up to a day ahead): heat the oven to 350°F. Line the bottom of a 9-inch round cake pan with a parchment circle. Melt 4 tbsp butter with the 1/2 cup brown sugar and 1/8 tsp salt in a small saucepan over medium heat, whisking 1 minute until smooth and bubbling. Pour into the lined pan and tilt to coat evenly.
8. Arrange the dried pineapple rings in a single snug layer over the caramel — 8 around the edge with 1 in the center, trimming to fit — and tuck a dry maraschino cherry into each ring hole, cut side up.
9. Whisk the 1 cup flour, baking powder, and 1/4 tsp salt together. In another bowl, beat the 6 tbsp softened butter with the 1/2 cup granulated sugar for 3 minutes until light, then beat in the egg and vanilla. Add the flour mixture in two additions alternating with the 1/3 cup pineapple juice, mixing just until smooth. Dollop the thick batter over the pineapple and spread gently to the edges with an offset spatula.
10. Bake at 350°F for 28 to 33 minutes, until golden and a toothpick in the center comes out clean. Cool in the pan exactly 10 minutes, then run a thin knife around the edge, invert onto a parchment-lined flat plate or tart-pan base, peel off the parchment, and cool completely — at least 1 hour. It will be about 3/4 inch tall.
11. For the glaze, simmer 3/4 cup pineapple juice with 2 tbsp brown sugar over medium heat until reduced to about 3 tablespoons and syrupy, 8 to 10 minutes. Off heat, whisk in 1 tbsp butter and a pinch of salt. Cool to warm.
12. Assemble: run a thin knife dipped in hot water around the chilled cheesecake, release the springform ring, and slide the cheesecake (still on its base) onto a serving plate. Slide the cooled cake layer, pineapple side up, off its parchment and onto the cheesecake, centering it. If the cake overhangs anywhere, trim the edge with a serrated knife.
13. Brush or drizzle the warm glaze over the pineapple, then chill the assembled cake 30 minutes to set. Slice with a long thin knife wiped clean and dipped in hot water between cuts; serve cold, with lightly whipped cream if you like.

Chef's tips

Nutrition (per serving, estimated)

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