Pineapple Upside Down Cupcakes

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

PREP TIME:20minutes minutes

COOK TIME:17minutes minutes

TOTAL TIME:37minutes minutes


  • 2 muffin pans
  • small and large mixing bowls
  • Whisk
  • Ingredients
  • ▢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 teaspoon canola oil 
  • ▢¾ cup granulated sugar 
  • ▢2 large eggs, room temperature
  • Instructions 
  • 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.
  • Notes
  • Substitutions
  • 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.

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