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- Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes
Ingredients
- cooking spray
- ½ cup butter
melted
- 1 ½ cups brown sugar
- 24 maraschino cherries
- 1 can crushed pineapple
20 ounce
- 1 package pineapple cake mix
18.25 ounce
- 1 ⅓ cups pineapple juice
- ⅓ cup vegetable oil
- 3 eggs
- 1 tablespoon confectioners' sugar for dusting
or as needed
Directions
- 1
Preheat the oven to 350 degrees F (175 degrees C). Move an oven rack to the middle of the oven. Spray 24 muffin cups with cooking spray.
- 2
Spoon 1 teaspoon melted butter into the bottom of each sprayed muffin cup. Spoon 1 tablespoon brown sugar into each muffin cup. Press a maraschino cherry into the center of the brown sugar in each muffin cup. Spoon a heaping tablespoon of crushed pineapple on top and compact it with the back of a spoon into an even layer.
- 3
Mix pineapple cake mix, pineapple juice, vegetable oil, and eggs in a large bowl with an electric mixer on low speed until moistened, about 30 seconds. Increase speed to medium; mix for 2 minutes.
- 4
Pour batter into the muffin cups, filling them to the top; do not overfill.
- 5
Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
- 6
Line a work surface with waxed paper. Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the waxed paper; serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with confectioners' sugar before serving.

Pineapple Upside Down Cupcakes
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Based on 285 ratings
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About this Recipe
Bring a touch of nostalgic charm to your next gathering with these delightful Pineapple Upside Down Cupcakes, a simplified classic perfect for any occasion. These individual treats offer all the beloved flavors of the traditional cake in a convenient, portable form.
Why This Recipe Works
This recipe takes the timeless appeal of pineapple upside down cake and makes it incredibly accessible. By starting with a readily available pineapple cake mix, you're set up for success, ensuring a moist, flavorful crumb with minimal fuss. It’s an easy, yummy, and streamlined approach to a dessert that consistently wows.
What to Expect
Prepare for a truly satisfying bite: a wonderfully moist and tender cupcake crowned with a shimmering, caramelized pineapple and a vibrant maraschino cherry. The sweet and tangy notes of the crushed pineapple beautifully complement the rich, buttery brown sugar topping, creating a harmonious burst of flavor. These individual portions are not only charming to look at but also perfectly sized, making them ideal for packing into lunches or serving a crowd at family gatherings.
Customization & Variations
While this recipe is a perfectly delicious simplified version, you can make small adjustments to suit your taste. For a slightly less intense cherry flavor, you can halve the maraschino cherries before placing them in the muffin tins. To ensure a thicker caramelized topping, make sure the crushed pineapple is very well drained before layering it into the cupcake tins.
Serving & Context
These delightful cupcakes are versatile and fitting for a variety of occasions, from potlucks and birthday parties to everyday family dinners. They are best served at room temperature, allowing the flavors to fully meld and the topping to remain soft and inviting.







