Name: Pineapple Upside-Down Cupcakes
Cook time: P0Y0M0DT0H55M0.000S
Total time: P0Y0M0DT2H25M0.000S
Yield: 12 servings
Ingredients: Nonstick cooking spray, for the muffin pan; 9 slices canned pineapple (from one 20-ounce can, juice reserved); 4 tablespoons unsalted butter; 3/4 cup firmly packed light brown sugar; 1/4 teaspoon kosher salt (see Cook’s Note); 1 teaspoon vanilla extract; 3/4 cup unsalted butter, at room temperature; 3/4 cup granulated sugar; 2 large eggs; 3/4 cup all-purpose flour; 1 1/2 teaspoons baking powder; 1/4 teaspoon kosher salt (see Cook’s Note); 1/2 cup sour cream; 2 tablespoons pineapple juice (from the canned pineapple); 1 teaspoon vanilla extract; 4 ounces cream cheese, at room temperature; 1/2 cup powdered sugar; 2 teaspoons vanilla extract; Pinch of kosher salt (see Cook’s Note); 1 cup heavy cream; 12 maraschino cherries with stems

Directions

Special equipment:

a 12-cup muffin pan; a large pastry bag; a round or fluted piping tip

Preheat the oven to 350 degrees F. Coat the cavities of a 12-cup muffin pan with the cooking spray.
For the pineapple topping: Finely chop 5 of the pineapple slices. Melt 2 tablespoons of the butter in a large skillet over medium heat. Add the chopped pineapple and cook until the liquid almost evaporates, and the pineapple is tender and falling apart, about 5 minutes. Stir in the remaining 2 tablespoons butter until melted. Stir in the brown sugar and salt and cook until the sugar melts and mixture is thick, 3 to 5 minutes. Remove the skillet from the heat and stir in the vanilla. Divide the pineapple mixture evenly into the bottoms of the prepared muffin cups. Set aside.
For the cupcakes: Finely dice the remaining 4 pineapple slices and set aside. Beat the butter and granulated sugar in a heavy-duty stand mixer fitted with the paddle attachment at medium speed until fluffy, 2 to 3 minutes. Add the eggs, one at a time, beating just until the yellow disappears.
Whisk together the flour, baking powder and salt in a medium bowl. Whisk together the sour cream, pineapple juice and vanilla in another medium bowl. Set the mixer on slow speed and add 1/3 of the flour mixture to the butter mixture then add half the sour cream mixture. Continue to alternate beginning and ending with the flour mixture. Stir in the reserved diced pineapple.
Divide the batter evenly between the muffin cups. Bake until a toothpick inserted in the centers comes out clean, 18 to 21 minutes. Remove the cupcakes from the oven and let cool in the pan for 10 minutes. Run a knife around the edges and turn out the cakes onto a parchment paper-lined rimmed baking sheet to cool completely, about 1 hour.
For the frosting: Beat the cream cheese, powdered sugar, vanilla and salt in a heavy-duty stand mixer fitted with the paddle attachment at medium speed until creamy, 2 minutes. Transfer the cream cheese mixture to a large bowl.
Wash and dry the stand mixer bowl and fit the stand mixer with the whisk attachment. Add the heavy cream to the stand mixer and beat until soft peaks form, 3 to 5 minutes. Add the cream cheese mixture to the whipped cream and beat until fluffy, 1 to 2 minutes longer.
Transfer the frosting to a large pastry bag fitted with a round or fluted piping tip. Pipe the frosting onto the cooled cupcakes and garnish with the maraschino cherries.

Cook’s Note

We use Diamond Crystal kosher salt, which is less dense than Morton. If you use Morton, just use a little less.

Pineapple Upside-Down Cupcakes

Ingredients

Pineapple Topping:

Cupcakes:

Frosting:

Directions

Special equipment:

Cook’s Note

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