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Homemade pineapple upside-down cupcakes recipe with caramelized pineapple rings and cherries on a white kitchen counter, overhead shot.

Pineapple Upside-Down Cupcakes Recipe

Moist and buttery pineapple upside-down cupcakes recipe with caramelized pineapple rings, cherries, and a fluffy vanilla base. Perfect for parties, potlucks, or a tropical homemade treat.
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Course: Cupcakes, Dessert
Cuisine: American, Tropical
Prep Time: 20 minutes
Cook Time: 25 minutes
Cooling/Flip: 5 minutes
Total Time: 50 minutes
Servings: 12 cupcakes
Calories: 240kcal
Cost: $8

Equipment

  • 1 12-cup muffin tin Heavy-duty, non-stick
  • 1 Stand or hand mixer For fluffy batter
  • 1 Large cutting board For the flip
  • 1 Small Ice Cream Scoop 2-tbsp size for even batter
  • 1 Mixing bowls Separate wet/dry ingredients

Ingredients

Topping

  • ¼ cup Butter, melted For topping
  • ½ cup Brown sugar, packed Light or dark
  • 12 whole Pineapple rings Canned or fresh
  • 12 whole Maraschino cherries Center garnish

Cupcake Batter

  • 2 tablespoon Pineapple juice From can or fresh
  • 1 ⅓ cups All-purpose flour Sifted
  • 1 cup Granulated sugar
  • cup Butter, softened For batter
  • 1 ½ teaspoon Baking powder
  • ½ teaspoon Salt
  • cup Whole milk Room temp
  • 1 large Egg Room temp
  • 1 teaspoon Vanilla extract Pure preferred

Instructions

  • Preheat oven to 350°F (175°C) and grease muffin tin.
  • Mix melted butter and brown sugar, add to cups with pineapple ring + cherry.
  • Cream butter and sugar, add egg + vanilla.
  • Combine dry ingredients, alternate with milk.
  • Fill cups ⅔ with batter, bake 20–25 min until golden.
  • Cool 5 min, loosen edges, flip onto board.

Notes

  • Nutrition information is automatically calculated, so should only be used as an approximation.

Nutrition

Serving: 85g | Calories: 240kcal | Carbohydrates: 38g | Protein: 2g | Fat: 9g | Saturated Fat: 5g | Polyunsaturated Fat: 0.5g | Monounsaturated Fat: 2g | Cholesterol: 35mg | Sodium: 180mg | Potassium: 95mg | Fiber: 1g | Sugar: 27g | Vitamin A: 250IU | Vitamin C: 2mg | Calcium: 40mg | Iron: 1mg