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Easy Pineapple Upside Down Cupcakes Recipe! Soft, buttery sweet cupcakes with a moist top, tender pineapple pieces, and cherry on top. 

Pineapple Upside Down Cupcakes

Easy Pineapple Upside Down Cupcakes Recipe! Soft moist cupcakes with tender pineapple pieces and cherry on top. 
Servings: 21 cupcakes
4.80 from 5 votes
Prep Time 20 minutes
Cook Time 17 minutes
Total Time 37 minutes


  • 2 muffin pans
  • small and large mixing bowls
  • Whisk


  • ½ cup butter, melted 
  • ½ cup brown sugar, packed 
  • 1 can (20 ounces) pineapple slices or chunks with juice, divided 
  • 21 maraschino cherries, stemless 
  • 2 cups all-purpose flour 
  • 2 teaspoons baking powder 
  • ½ teaspoon salt 
  • ½ teaspoon baking soda 
  • ¼ cup canola oil 
  • ¾ cup granulated sugar 
  • 2 large eggs, room temperature 


  • Preheat the oven to 350°F
  • Divide the pineapple and juice.
  • Cut the pineapple into small pieces that are about 1/2 an inch square.
  • Spoon 1 teaspoon of melted buFer into the muffin pans. Sprinkle about 1 teaspoon of brown sugar over the buFer. Pl
  • Place 4 pieces of pineapple into a flower or cross shape in each cup, and place 1 cherry in the middle of the pieces. Set the pan aside. 
  • In a small bowl, whisk together the "dry ingredients" (flour, baking powder, salt, and baking soda).
  • In a separate large mixing bowl, whisk the oil and sugar together then beat in the eggs until just combined. Mix in the "dry ingredients" with a spatula.
  • When the batter starts to get too thick and dry, pour in the pineapple juice. Continue mixing until the batter is wet and thick. 
  • Spoon the batter over the pineapple pieces, about 2 tablespoons into each cup. The cups will be almost full.
  • Bake the cupcakes, one batch at a time for 15-17 minutes or until the edges are golden brown and a toothpick inserted into the middle cupcakes comes out clean. It’s okay if some of the butter has seeped out of the top. 
  • Let the cupcakes cool for 30 minutes, then run a thin, small knife around the edge of each cupcake to help release them from the pan.
  • Carefully remove each cupcake and place it “upside-down” on a cooling rack.


  • You can use salted butter instead of unsalted butter. 
  • Dark brown sugar and light brown sugar work the same in this recipe.
  • Use vegetable oil instead of canola oil.


Calories: 161kcalCarbohydrates: 28gProtein: 2gFat: 5gSaturated Fat: 3gPolyunsaturated Fat: 0.3gMonounsaturated Fat: 1gTrans Fat: 0.2gCholesterol: 27mgSodium: 165mgPotassium: 61mgFiber: 1gSugar: 18gVitamin A: 173IUVitamin C: 3mgCalcium: 39mgIron: 1mg