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–+ servings
Pineapple upside down cupcakes on parchment paper.
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Pineapple Upside Down Cupcakes

These Pineapple Upside Down Cupcakes are the perfect dessert for any party, potluck, or holiday gathering. Made with a box of cake mix and ready in about 35 minutes, just flip them out of the pan, and that gorgeous caramelized topping does all the work for you.
Author: Nikki Lee
Servings: 24 cupcakes
Prep Time 15 minutes
Cook Time 20 minutes
Total Time 35 minutes

Equipment

  • 2 muffin pans (or make in 2 batches)

Ingredients 

Cake batter

  • 1 box pineapple cake mix or yellow
  • 3 large eggs
  • ½ cup vegetable oil
  • 1 cup pineapple juice

Topping (per cupcake amounts)

  • 1 cup butter melted (about 1 tsp per cup)
  • 24 maraschino cherries patted dry (1 each)
  • 1½ cups brown sugar about 2 tsp per cup
  • 4 cups crushed pineapple well-drained (about 1 TBSP per cup) - reserve the juice. You will need 2 - 20 ounce cans.

Instructions

  • Preheat the oven to 350℉ degrees.
  • Spray two 12 count cupcake or muffin pans with non-stick cooking spray.
  • Mix cake mix, oil, eggs and pineapple juice on low speed of mixer until combined. Switch to medium speed and mix for about 2 min.
  • Spoon 1 teaspoon melted butter in the bottom of each muffin cup.
  • Add 2 teaspoons of brown sugar to each cup. Slightly press it down with the measuring spoon so it is evenly distributed in the bottom of each muffin cup.
  • Place a cherry in the center of the brown sugar and lightly press it into the brown sugar.
  • Add 1 tablespoon of the crushed pineapple to each cup and use a spoon to evenly distribute it in the bottom of each muffin cup.
  • Scoop the cake batter into each muffin cup, fill about ¾ the way full.
  • Bake on the center rack of the oven for 20 minutes or until a toothpick inserted in the center comes out clean. (Only push the toothpick part way into the cupcake so you don’t reach it into the pineapple mixture.)
  • Remove from the oven and allow the cupcakes to cool for about 5-10 minutes.
  • Place parchment or wax paper on the counter surface.
  • Then use a knife to gently loosen the cupcake from the edges of the pan before inverting. Place a wire cooling rack over the cupcake tin and, carefully, using potholders, keep the cooling rack pressed securely against the tin, and invert cupcakes onto the cooling rack. Lay the cooling rack on the parchment paper (you could also use a baking sheet) Lift the tin, the cupcakes should release easily. Be sure each cupcake is right side up.

Notes

  • Do not use cupcake liners. The brown sugar and butter need direct contact with the metal pan to caramelize properly.
  • Drain the crushed pineapple really well before using. Press it between paper towels if it still seems wet. Too much moisture and you will lose that caramelized topping.
  • Pat the maraschino cherries dry before placing them in the cups. They hold more liquid than you think.
  • When testing for doneness, insert the toothpick only partway into the cupcake. You want to stay in the cake layer and not hit the pineapple topping underneath.
  • Let the cupcakes rest in the pan for 5 to 10 minutes after baking before flipping them out. Too soon, and they fall apart. Too long and the topping sticks.

Nutrition

Serving: 1 cupcake | Calories: 165 kcal | Carbohydrates: 23 g | Protein: 1 g | Fat: 8 g | Saturated Fat: 5 g | Polyunsaturated Fat: 0.4 g | Monounsaturated Fat: 2 g | Trans Fat: 0.3 g | Cholesterol: 41 mg | Sodium: 73 mg | Potassium: 91 mg | Fiber: 1 g | Sugar: 22 g | Vitamin A: 289 IU | Vitamin C: 5 mg | Calcium: 27 mg | Iron: 0.4 mg

Find it online:

www.soulfullymade.com/pineapple-upside-down-cupcakes/