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pineapple upside-down cupcakes

How to Make the Best Pineapple Upside-Down Cupcakes

These Pineapple Upside-Down Cupcakes are a mini twist on the classic dessert, featuring buttery caramelized pineapple and cherries over a soft, fluffy vanilla cake. They’re easy to make, perfectly portioned, and a tropical delight for any occasion!
Prep Time 15 minutes
Cook Time 20 minutes
Total Time 35 minutes
Course Dessert
Cuisine American
Servings 12 Cupcakes
Calories 220 kcal

Ingredients
  

  • For the Topping:
  • ¼ cup unsalted butter melted
  • ½ cup light brown sugar packed
  • 12 maraschino cherries
  • 1 20 oz can pineapple slices, drained and cut into small pieces
  • For the Cupcake Batter:
  • 1 ¼ cups all-purpose flour
  • 1 ½ tsp baking powder
  • ¼ tsp salt
  • ½ cup unsalted butter softened
  • ¾ cup granulated sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • ½ cup pineapple juice from the canned pineapple
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Instructions
 

  • Preheat & Prepare the Cupcake Pan:
  • Preheat oven to 350°F (175°C).
  • Grease a 12-cup muffin tin or line with paper liners.
  • Make the Topping:
  • In a small bowl, mix melted butter and brown sugar.
  • Spoon 1 teaspoon of the mixture into the bottom of each cupcake well.
  • Place a cherry in the center and arrange pineapple pieces around it.
  • Make the Cupcake Batter:
  • In a medium bowl, whisk together flour, baking powder, and salt.
  • In a large bowl, beat butter and sugar until fluffy.
  • Add eggs one at a time, beating well. Stir in vanilla extract.
  • Alternate adding dry ingredients and pineapple juice, mixing until smooth.
  • Assemble And Bake:
  • Spoon batter over the pineapple topping, filling each cup about ¾ full.
  • Bake for 18-22 minutes, or until a toothpick comes out clean.
  • Flip And Serve:
  • Let cool for 5 minutes, then invert the cupcakes onto a baking sheet or plate while still warm.
  • Serve warm or at room temperature!

Notes

  • For Extra Moisture: Add 2 tbsp sour cream to the batter.
  • Make It Boozy: Brush cupcakes with a rum glaze after baking!
  • Storage: Store in an airtight container at room temperature for up to 2 days or refrigerate for 5 days.

Nutrition

Calories: 220kcalCarbohydrates: 30gProtein: 2gFat: 10g