Pineapple Upside-Down Cupcakes

Here’s a detailed recipe for Pineapple Upside-Down Cupcakes—sweet, moist, and full of tropical flavor. 🍍

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Pineapple Upside-Down Cupcakes

Ingredients

For the Topping:

• 1/4 cup (60 g) unsalted butter, melted

• 1/2 cup (100 g) brown sugar, packed

• Pineapple slices (fresh or canned), cut to fit cupcake tins

• Maraschino cherries (optional), halved

For the Cupcake Batter:

• 1 1/2 cups (190 g) all-purpose flour

• 1 teaspoon baking powder

• 1/4 teaspoon baking soda

• 1/4 teaspoon salt

• 1/2 cup (115 g) unsalted butter, softened

• 3/4 cup (150 g) granulated sugar

• 2 large eggs, room temperature

• 1 teaspoon vanilla extract

• 1/2 cup (120 ml) buttermilk (or milk + 1 tsp vinegar)

• 1/2 cup crushed pineapple, drained

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Instructions

Step 1: Prepare the Topping

1. Preheat the oven to 350°F (175°C).

2. In a small bowl, mix melted butter and brown sugar.

3. Spoon about 1 tablespoon of this mixture into the bottom of each cupcake liner.

4. Place a pineapple slice (or smaller piece) on top of the brown sugar, and add a cherry in the center if desired.

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Step 2: Make the Cupcake Batter

1. In a medium bowl, whisk together flour, baking powder, baking soda, and salt.

2. In a large bowl, beat softened butter and sugar until light and fluffy.

3. Add eggs, one at a time, beating well after each addition.

4. Mix in vanilla extract.

5. Alternately add the dry ingredients and buttermilk to the butter mixture, starting and ending with dry ingredients. Mix until just combined.

6. Fold in the crushed pineapple.

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Step 3: Assemble the Cupcakes

1. Spoon the batter over the pineapple and brown sugar in each cupcake liner, filling about 2/3 full.

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Step 4: Bake

1. Bake for 18–22 minutes, or until a toothpick inserted into the center comes out clean.

2. Let the cupcakes cool in the pan for 5–10 minutes.

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Step 5: Invert and Serve

1. Carefully run a knife around the edges of the cupcakes.

2. Place a cooling rack or plate over the cupcake tin and invert to release the cupcakes.

3. The pineapple and brown sugar topping should now be on top, caramelized and glossy.

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Tips for Perfect Pineapple Upside-Down Cupcakes

• Use fresh pineapple if possible—it gives a brighter flavor than canned.

• Don’t overbake; the brown sugar topping can burn quickly.

• If your cupcakes stick when inverting, gently tap the bottom or use a small spatula to help release.

• For extra tropical flavor, add a teaspoon of coconut extract to the batter.