Pineapple Upside-Down Cupcakes

These Pineapple Upside-Down Cupcakes are a fun, individual-sized version of the traditional cake, packed with tropical flavors. A buttery brown sugar topping, sweet pineapple, and bright maraschino cherries create a delightful caramelized layer that complements the fluffy pineapple cake. With their beautiful presentation and irresistible taste, these cupcakes are perfect for parties or special occasions!

Why You’ll Love This Recipe:

Tropical Flavors: The combination of pineapple, brown sugar, and maraschino cherries gives these cupcakes a classic tropical flavor that feels like a vacation in every bite.
Individual Portions: These cupcakes are perfectly portioned, making them great for sharing or enjoying on-the-go.
Easy to Make: With the help of a cake mix, these cupcakes come together quickly with minimal effort, while still tasting homemade.
Versatile: You can serve them as is or dress them up with a dusting of sugar or a dollop of whipped cream for an extra special touch.

Key Ingredients:

Cake Mix: You can use a yellow cake mix or vanilla cake mix if you can’t find pineapple-flavored cake mix. Add a teaspoon of pineapple extract to boost the flavor.
Maraschino Cherries: If you prefer, you can replace the cherries with fresh or canned pineapple chunks for an all-pineapple topping.
Butter Substitute: You can substitute the butter with margarine or coconut oil for a dairy-free option. Coconut oil will add an extra tropical flair to the cupcakes.
Pineapple Juice: If your canned pineapple doesn’t yield enough juice, you can add a bit of water or extra store-bought pineapple juice to make up the difference.

Complete list of ingredients with quantities and instructions is located in the recipe card below

Step-by-Step Instructions

Step 1: Preheat the Oven

Preheat the Oven: Set your oven to 350°F (175°C) to ensure it’s ready for baking once the cupcakes are assembled.
Prepare the Muffin Cups: Spray 24 muffin cups with cooking spray. This prevents the cupcakes from sticking, making them easy to remove after baking.

Step 2: Prepare the Topping

Melt the Butter: Place 1 teaspoon of melted butter into each muffin cup.
Add Brown Sugar and Cherry: Add 1 tablespoon of brown sugar on top of the butter in each muffin cup, then press a maraschino cherry into the center of the brown sugar.
Add Crushed Pineapple: Spoon a heaping tablespoon of well-drained crushed pineapple over the cherry and brown sugar mixture. Press down gently to create an even layer, ensuring it covers the bottom of each muffin cup.

Step 3: Mix the Cake Batter

Prepare the Batter:

In a large mixing bowl, combine:
1 box of pineapple cake mix
Reserved pineapple juice (from the crushed pineapple)
3 eggs
1/3 cup vegetable oil
Mix: Start mixing on low speed for 30 seconds to moisten the ingredients. Increase the speed to medium and beat for 2 minutes until the batter is smooth and well-combined.

Step 4: Fill the Muffin Cups

Pour the Batter: Pour the prepared cake batter into the muffin cups, filling each one about 2/3 full. This allows room for the cupcakes to rise as they bake.

Step 5: Bake the Cupcakes

Bake: Place the muffin tin into the preheated oven and bake for about 20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
Be Careful: Avoid overbaking to keep the cupcakes moist and tender.

Step 6: Cool and Invert

Cool Slightly: Let the cupcakes cool in the pan for 5 minutes. This allows the topping to set slightly, making it easier to invert without spilling.
Invert the Cupcakes: Run a knife around the edges of each cupcake to loosen them. Carefully invert the muffin tin onto a baking sheet lined with wax paper. The pineapple and brown sugar topping should come out beautifully.

Step 7: Dust with Sugar

Dust with Confectioners’ Sugar: For an extra touch of sweetness and a pretty finish, lightly dust the tops of the cupcakes with confectioners’ sugar before serving.

Serving Suggestions:

These Pineapple Upside-Down Cupcakes are best enjoyed warm, but they’re just as delicious at room temperature. Here are a few ways to serve them:

With Ice Cream: Serve each cupcake with a scoop of vanilla ice cream for a classic pairing. The cold, creamy ice cream is perfect with the warm, caramelized pineapple.
Whipped Cream: Top each cupcake with a dollop of whipped cream for a light, fluffy addition.
Toasted Coconut: Sprinkle some toasted coconut flakes over the cupcakes for a tropical, crunchy finish.

Storage and Reheating Tips:

Refrigerate: Store any leftover cupcakes in an airtight container in the refrigerator for up to 3 days. They can be enjoyed cold or reheated.

Reheat: To reheat, warm the cupcakes in the microwave for 15-20 seconds or place them in a 350°F (175°C) oven for 5 minutes until warm.

Freeze: These cupcakes freeze well! Wrap each cupcake individually in plastic wrap and store them in a freezer-safe container for up to 3 months. Thaw overnight in the fridge before serving.

Recipe Variations:

Pineapple and Coconut Cupcakes: Add 1/2 cup shredded coconut to the cake batter for an extra tropical twist.
Rum-Spiked Topping: For a grown-up version, mix a tablespoon of dark rum into the melted butter and brown sugar mixture for a Pina Colada-inspired dessert.
Mini Pineapple Upside-Down Cupcakes: Use a mini muffin tin to make bite-sized versions of this classic dessert. Just reduce the baking time to about 12-15 minutes.

Conclusion:

These Pineapple Upside-Down Cupcakes bring all the classic flavors of the traditional cake in a fun, individual-sized portion. With a rich, buttery topping and moist pineapple-infused cake, they’re perfect for any occasion—from summer barbecues to holiday desserts. Once you try these, they’re sure to become a regular in your dessert rotation!