Pineapple Upside Down Cupcakes

Why You’ll Love This Recipe

These cupcakes deliver the nostalgic flavor of the traditional pineapple upside down cake in a convenient handheld size. They’re easy to make, impressive to serve, and perfectly portioned. The combination of caramelized brown sugar, juicy pineapple, and tender cake makes them irresistible. Plus, they’re festive enough for celebrations yet simple enough for everyday baking.

Ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

• Pineapple rings (canned or fresh, cut to fit the muffin tin)

• Maraschino cherries

• Brown sugar

• Unsalted butter, melted

• All-purpose flour

• Baking powder

• Salt

• Granulated sugar

• Eggs

• Vanilla extract

• Milk or pineapple juice

Directions

1. Preheat oven to 350°F (175°C). Grease a muffin tin well.

2. In each muffin cup, spoon about 1 teaspoon melted butter and 1 teaspoon brown sugar.

3. Place a small pineapple ring (or piece of pineapple) in each cup, then place a cherry in the center.

4. In a mixing bowl, whisk together flour, baking powder, and salt.

5. In another bowl, beat sugar, eggs, and vanilla until fluffy. Add milk (or pineapple juice) and mix well.

6. Stir the dry ingredients into the wet ingredients until just combined.

7. Pour batter over the pineapple in each muffin cup, filling about 2/3 full.

8. Bake for 20–25 minutes, until a toothpick comes out clean.

9. Let cool for 5 minutes, then carefully invert the cupcakes onto a tray or parchment paper.

10. Serve warm or at room temperature.

Servings and timing

This recipe makes 12 cupcakes.
Preparation time: 15 minutes
Cooking time: 20–25 minutes
Total time: 35–40 minutes

Variations

• Use crushed pineapple instead of rings for a different texture.

• Add shredded coconut to the batter for a tropical twist.

• Make mini cupcakes for bite-sized treats.

• Use pineapple juice in the batter for extra pineapple flavor.

• Swap maraschino cherries for fresh cherries or omit them if preferred.

Storage/Reheating

Store cupcakes in an airtight container at room temperature for up to 2 days or in the refrigerator for up to 4 days. To reheat, microwave each cupcake for about 10–15 seconds to bring back its warmth and softness. These cupcakes also freeze well for up to 2 months; thaw overnight in the refrigerator before serving.

FAQs

Can I use fresh pineapple?

Yes, just cut it into small pieces that fit inside the muffin tin.

Do I need to line the muffin tin with paper liners?

No, it’s best to bake directly in a greased muffin tin so the pineapple topping caramelizes properly.

Can I use cake mix for the batter?

Yes, a yellow or vanilla cake mix works great and makes the recipe even easier.

Why did my cupcakes stick to the pan?

Make sure to grease the tin generously and let the cupcakes cool for a few minutes before inverting.

Can I make these ahead of time?

Yes, they can be baked a day in advance and stored in the fridge, then served chilled or gently warmed.

What should I serve with pineapple upside down cupcakes?

They’re delicious on their own, but whipped cream or vanilla ice cream makes a great pairing.

Can I make them gluten-free?

Yes, use a gluten-free flour blend designed for baking.

Can I use mini muffin tins?

Yes, just reduce the baking time to about 12–15 minutes.

How do I keep the pineapple from sinking?

The pineapple should stay on top (once inverted) as long as the batter isn’t too runny. Be sure not to overfill the cups.

Do these taste better warm or cold?

They’re wonderful both ways—warm for a gooey caramel topping, or cold for a firmer, refreshing bite.

Conclusion

Pineapple Upside Down Cupcakes are a delightful, tropical dessert that’s easy to make and always a hit. With their caramelized fruit topping and moist cake base, they bring the charm of a retro classic into a modern, individual serving size. Perfect for parties, potlucks, or family desserts, these cupcakes are sure to brighten any occasion.

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