Pineapple Upside Down Cupcakes
These delightful Pineapple Upside Down Cupcakes feature moist vanilla cake topped with caramelized brown sugar, juicy pineapple rings, and maraschino cherries. Each bite delivers the perfect balance of buttery sweetness and tropical tang in individual servings.
Ingredients
For the Topping
- 4 tablespoons unsalted butter melted
- 1/2 cup brown sugar packed
- 12 pineapple rings from a 20 oz can, drained and patted dry
- 12 maraschino cherries stems removed and patted dry
For the Cake Batter
- 1 1/2 cups all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/4 teaspoon salt
- 1/2 cup unsalted butter softened to room temperature
- 3/4 cup granulated sugar
- 2 large eggs at room temperature
- 1 teaspoon vanilla extract
- 1/4 cup pineapple juice reserved from the canned pineapple
- 1/4 cup buttermilk or substitute with regular milk mixed with 1/4 teaspoon lemon juice
Instructions
- Preheat your oven to 350°F (175°C) and line a standard 12-cup muffin tin with paper liners. Spray the liners lightly with non-stick cooking spray to prevent sticking.
- Prepare the caramel base by mixing melted butter and brown sugar in a small bowl until well combined. Distribute about 2 teaspoons of this mixture into the bottom of each cupcake liner, spreading it evenly.
- Arrange one pineapple ring on top of the caramel mixture in each liner. You may need to trim the rings slightly to fit. Place a maraschino cherry in the center of each pineapple ring.
- Whisk together the dry ingredients in a medium bowl – flour, baking powder, and salt – then set aside. This ensures even distribution of leavening agents throughout your batter.
- Cream the butter and sugar in a large bowl using an electric mixer on medium-high speed for about 3 minutes, until light and fluffy. This incorporates air into the batter for a lighter texture.
- Add eggs one at a time, beating well after each addition. Then mix in the vanilla extract until fully incorporated.
- Combine the pineapple juice and buttermilk in a small measuring cup and stir briefly.
- Alternate adding the dry ingredients and wet mixture to the butter mixture, beginning and ending with the dry ingredients (three additions of dry, two of wet). Mix on low speed just until combined after each addition, being careful not to overmix.
- Spoon the batter carefully over the pineapple arrangement in each liner, filling each cup about 3/4 full. The batter should come to just below the top of each liner.
- Bake for 22-25 minutes or until a toothpick inserted in the center comes out clean and the tops spring back when lightly touched.
- Cool the cupcakes in the pan for exactly 5 minutes – this timing is crucial! If you flip too soon, they’ll fall apart; too late, and the caramel will harden, making them stick.
- Invert each cupcake carefully onto a wire rack by placing the rack on top of the muffin tin and flipping it over in one quick motion. Gently remove the liners while the cupcakes are still warm.
- Allow to cool completely before serving, though these cupcakes are also delicious when served slightly warm.
Notes
- For perfectly sized pineapple rings, look for canned pineapple tidbits or chunks if the rings are too large for your muffin cups. Alternatively, use a small round cookie cutter to trim standard rings.
- These cupcakes are best enjoyed within 24 hours of baking when the caramel topping is at its most luscious texture.
- Store any leftovers in an airtight container at room temperature for up to 2 days, or refrigerate for up to 5 days.
- For a tropical twist, add 1/2 teaspoon of coconut extract to the batter or sprinkle toasted coconut flakes around the edges after inverting.
- If you’re preparing for a party, you can make the batter and prepare the caramel topping a day ahead, but assemble and bake on the day of serving for best results.