These Pineapple Upside Down Cupcakes are a fun and delicious twist on the classic retro dessert. Each cupcake features sweet caramelized pineapple, juicy cherries, and moist vanilla cake baked into perfectly portioned treats. They’re buttery, fruity, and perfect for parties, potlucks, or anytime you want a nostalgic dessert everyone will love.
Prep Time
- Prep Time: 20 minutes
- Cook Time: 22 minutes
- Cooling Time: 10 minutes
- Total Time: 52 minutes
- Servings: 12 cupcakes
Equipment
- Muffin tin
- Cupcake liners or nonstick spray
- Mixing bowls
- Electric mixer or whisk
- Measuring cups and spoons
- Spatula
- Cooling rack
Ingredients
Topping
- 1/4 cup melted butter
- 1/2 cup brown sugar
- 6 pineapple rings, cut in halves
- 12 maraschino cherries
Cupcake Batter
- 1 1/2 cups all-purpose flour
- 1 teaspoon baking powder
- 1/4 teaspoon salt
- 1/2 cup unsalted butter, softened
- 3/4 cup granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 1/2 cup pineapple juice
- 1/4 cup milk
Ingredient Notes
- Pineapple: Canned pineapple rings work best and are easy to use.
- Cherries: Maraschino cherries add classic sweetness and color.
- Pineapple Juice: Enhances the tropical flavor and keeps cupcakes moist.
- Butter: Use real butter for rich flavor and caramelization.
Instructions
- Preheat oven to 350°F (175°C). Grease a 12-cup muffin tin well.
- Pour about 1 teaspoon melted butter into each muffin cup.
- Sprinkle brown sugar evenly over the butter.
- Place a pineapple half inside each cup and add a cherry in the center.
- In a bowl, whisk flour, baking powder, and salt together.
- In another bowl, beat softened butter and sugar until light and fluffy.
- Add eggs one at a time, then mix in vanilla extract.
- Alternate adding dry ingredients with pineapple juice and milk, mixing until smooth.
- Spoon batter evenly into muffin cups, filling about 3/4 full.
- Bake for 20–22 minutes or until a toothpick inserted comes out clean.
- Cool for 5–10 minutes, then carefully invert cupcakes onto a tray or cooling rack.
- Serve warm or at room temperature.
Nutrition Facts
(Approximate per cupcake)
- Calories: 240
- Carbohydrates: 33g
- Protein: 3g
- Fat: 11g
- Saturated Fat: 6g
- Sugar: 22g
- Sodium: 140mg
Tips
- Don’t let the cupcakes cool too long before inverting or the topping may stick.
- Pat pineapple slices dry to prevent excess moisture.
- Use silicone muffin pans for easier release.
- Serve with whipped cream or vanilla ice cream for extra indulgence.
Variations
- Coconut Version: Add shredded coconut to the batter.
- Rum Flavor: Mix a splash of rum extract into the batter for tropical flavor.
- Mini Cupcakes: Make bite-sized versions using a mini muffin tin.
- Cherry-Free: Skip cherries and add chopped pecans instead for crunch.