Description

Delight in these Pineapple Upside-Down Cupcakes, a tropical twist on the classic dessert that combines caramelized brown sugar, juicy pineapple, and maraschino cherries atop moist yellow cake batter. Perfectly portioned as individual cupcakes, they offer a fun and easy way to enjoy the flavors of a traditional pineapple upside-down cake with minimal effort and maximum flavor.

Ingredients

Scale

Topping

1/4 cup unsalted butter (melted)
1/2 cup brown sugar (packed)
1 (20-ounce) can pineapple slices, cut into small chunks
12 maraschino cherries (halved)

Cake Batter

1 box yellow cake mix
Ingredients listed on the cake mix box (usually eggs, oil, and water)

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Instructions

Preheat and Prepare Muffin Tin: Preheat your oven to 350°F (175°C). Lightly grease a 12-cup muffin tin thoroughly; do not use cupcake liners to allow easy inversion later.
Mix Butter and Brown Sugar: In a small bowl, combine the melted unsalted butter with the packed brown sugar, mixing well until combined.
Add Topping to Muffin Cups: Spoon about 1 tablespoon of the butter-brown sugar mixture into the bottom of each muffin cup to create a caramel base.
Place Pineapple and Cherry Pieces: Arrange a few small pineapple chunks on top of the sugar mixture in each cup, then add half a maraschino cherry (with the cut side facing up) over the pineapple to decorate.
Prepare Cake Batter: Following the instructions on the yellow cake mix box, prepare the batter by adding required eggs, oil, and water and mixing until smooth.
Fill Muffin Cups with Batter: Pour the prepared cake batter into each muffin cup, filling approximately three-quarters full to give the cupcakes room to rise.
Bake Cupcakes: Place the muffin tin in the oven, baking for 20 to 25 minutes or until a toothpick inserted into the center of a cupcake comes out clean.
Cool and Invert: Allow the cupcakes to cool in the pan for 5 minutes. Then, carefully run a knife around the edges of each cupcake to loosen them. Invert the cupcakes onto a wire rack or tray so the pineapple topping is on top.
Serve: Serve the cupcakes warm or at room temperature for the best flavor and texture.

Notes

If using pineapple tidbits or crushed pineapple instead of slices, ensure they are well-drained to prevent sogginess in the cupcakes.
These cupcakes are best enjoyed the day they are made for optimum freshness and texture.
You can store leftover cupcakes covered at room temperature for up to 2 days.

Prep Time: 15 minutes
Cook Time: 25 minutes
Category: Dessert
Method: Baking
Cuisine: American

Nutrition

Serving Size: 1 cupcake
Calories: 260
Sugar: 25g
Sodium: 280mg
Fat: 10g
Saturated Fat: 3g
Unsaturated Fat: 6g
Trans Fat: 0g
Carbohydrates: 39g
Fiber: 1g
Protein: 2g
Cholesterol: 35mg