These Pineapple Upside-Down Cupcakes are a delightful twist on the classic dessert, perfect for parties and individual servings. Each cupcake features a sweet, sticky pineapple topping with a maraschino cherry in the center, sitting atop a moist and buttery vanilla cake. The tropical flavors combined with a rich caramel glaze make these bite-sized treats irresistible!

Ingredients

For the topping

• ½ cup (113 g) unsalted butter, melted
• ¾ cup (150 g) brown sugar
• 12 pineapple slices (canned or fresh)
• 12 maraschino cherries

For the cupcake batter

• 1 ½ cups (190 g) all-purpose flour
• 1 ½ teaspoons baking powder
• ¼ teaspoon salt
• ½ cup (113 g) unsalted butter, softened
• ¾ cup (150 g) granulated sugar
• 2 large eggs
• 1 teaspoon vanilla extract
• ½ cup (120 ml) whole milk

Directions

Prepare the topping

1. Preheat the oven to 350°F (175°C). Grease a 12-cup muffin pan generously.
2. In a small bowl, mix the melted butter and brown sugar until well combined.
3. Spoon about 1 tablespoon of the butter-sugar mixture into the bottom of each muffin cup.
4. Place a pineapple slice on top of the sugar mixture, trimming it if necessary to fit. Add a maraschino cherry in the center of each pineapple slice.

Make the batter

5. In a medium bowl, whisk together the flour, baking powder, and salt.
6. In a large bowl, cream the softened butter and granulated sugar until light and fluffy. Add the eggs, one at a time, beating well after each addition. Stir in the vanilla extract.
7. Gradually add the dry ingredients to the wet mixture, alternating with the milk, beginning and ending with the flour mixture. Mix until just combined.
8. Spoon the batter over the pineapple slices, filling each cup about ¾ full.

Bake and cool

9. Bake in the preheated oven for 20-25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
10. Let the cupcakes cool in the pan for 5-10 minutes. Run a knife around the edges to loosen, then carefully invert the pan onto a large baking sheet to release the cupcakes.

Notes

• Pineapple options: Canned pineapple rings work best for this recipe, but fresh pineapple slices can be used for a more vibrant flavor.
• Cherry alternatives: If you’re not a fan of maraschino cherries, you can substitute with fresh berries or omit them altogether.
• Serving suggestion: These cupcakes are best enjoyed warm but can be stored in an airtight container at room temperature for up to 2 days.

Conclusion

These Pineapple Upside-Down Cupcakes are a fun and delicious way to enjoy a classic dessert in portable portions. Whether it’s for a picnic, a party, or just a sweet indulgence, these cupcakes are guaranteed to bring a taste of the tropics to any occasion. Give them a try, and you’ll be hooked on their sweet, buttery goodness!