Pineapple Upside-Down Cupcakes
Pineapple Cupcakes
Tender vanilla cupcakes baked over buttery brown sugar pineapple and cherries, then turned out glossy and caramelized for a playful individual dessert.
Pineapple upside-down cupcakes keep the charm of the classic skillet cake but turn it into neat little servings with golden edges and a glossy fruit topping. Each muffin cup gets melted butter, brown sugar, pineapple, and a cherry before the vanilla batter goes in, so the topping caramelizes directly against the pan.
The key is cutting the pineapple rings into tidy pieces that fit the bottom of each cup without crowding. A standard muffin pan works well, and a light coating of baking spray helps the cupcakes release cleanly after a short rest. Turn them out while they are still warm so the brown sugar syrup stays fluid and coats the fruit.
These cupcakes are best the day they are baked, when the cake is soft and the topping tastes bright and buttery. Serve them as they are, or add a small spoonful of whipped cream once they have cooled to room temperature.
Nutrition (per serving)
Directions
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1
Heat the oven to 350°F and coat a 12-cup standard muffin pan well with baking spray.
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2
Spoon 1 teaspoon melted butter into each muffin cup, then sprinkle about 1 tablespoon brown sugar over the butter.
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3
Cut each pineapple ring into 4 pieces and arrange 2 pieces in each muffin cup with 1 cherry in the center.
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4
Whisk the flour, baking powder, and salt in a medium bowl until evenly combined.
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5
In a separate bowl, whisk the remaining melted butter with the granulated sugar, eggs, and vanilla until smooth.
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6
Stir the milk and pineapple juice into the wet ingredients, then fold in the flour mixture just until no dry streaks remain.
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7
Divide the batter over the pineapple, filling each cup about three-quarters full and smoothing the tops gently.
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8
Bake for 20 to 25 minutes, until the cupcakes are golden and a toothpick inserted into the cake portion comes out clean.
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9
Cool in the pan for 5 minutes, then run a thin knife around each cupcake and invert the pan onto a rimmed tray.
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10
Lift off the pan carefully and spoon any syrup left behind over the warm cupcakes before serving.
Ingredients
- Unsalted butter, melted:6 tbsp
- Packed light brown sugar:2/3 cup
- Pineapple rings in juice, drained:6
- Maraschino cherries, drained and patted dry:12
- All-purpose flour:1 1/4 cups
- Baking powder:1 1/2 tsp
- Fine salt:1/4 tsp
- Granulated sugar:1/2 cup
- Large eggs:2
- Vanilla extract:1 1/2 tsp
- Whole milk:1/2 cup
- Reserved pineapple juice:2 tbsp
Tips & Notes
- Pat the cherries dry so their color stays bright without bleeding too much into the cake.
- Use pineapple packed in juice rather than heavy syrup to keep the topping sweet but balanced.
- Set the muffin pan on a rimmed baking sheet if the cups are very full, since the brown sugar syrup can bubble.
