Pineapple Upside Down Cupcake Bliss

Name: Pineapple Upside Down Cupcake Bliss
Prep time: 20 min
Cook time: 20 min
Total time: 40 min
Yield: 12 cupcakes
Ingredients: 1 cup all-purpose flour; 1 tsp baking powder; 1/2 tsp baking soda; 1/4 tsp salt; 1/2 cup unsalted butter, softened; 1 cup granulated sugar; 2 large eggs; 1 tsp vanilla extract; 1/2 cup buttermilk; 1/4 cup unsalted butter; 1/2 cup packed brown sugar; 1 can of pineapple rings, drained; 12 maraschino cherries

Highlighted under: Easy Baking Recipes

I absolutely adore these Pineapple Upside Down Cupcakes! Each bite takes me back to sunny afternoons, where the sweet and tangy flavors of pineapple paired delightfully with buttery cake. The caramelized brown sugar and butter topping creates a warm, inviting aroma that fills the kitchen as they bake. With a crown of maraschino cherries for that nostalgic touch, these cupcakes are not just a treat; they are a celebration of flavor! Perfect for gatherings or a special dessert, these cupcakes will surely impress your guests.

Created by

Emily

Last updated on 2026-02-07T20:42:28.261Z

When I first attempted to make Pineapple Upside Down Cupcakes, I was nervous about getting the caramelization just right. After several tries, I discovered that melting the butter with brown sugar in the muffin tins before adding the pineapple and cupcake batter made all the difference. The result was a perfectly sticky, sweet topping that layered beautifully onto the fluffy cupcakes.

I love experimenting with flavors, and I found that using fresh pineapple instead of canned fruit enhanced the overall taste. The fresh fruit provides a burst of juiciness, making each cupcake moist and delicious. Trust me, using fresh pineapple is a game changer!

Why You'll Love These Cupcakes
A delightful twist on a classic dessert
Moist and fluffy texture complemented by caramelized sweetness
Perfect for parties, gatherings, or a sweet treat to share

The Perfect Cupcake Technique

When making the cupcake batter, ensuring the butter is at room temperature is crucial for achieving the desired fluffiness. It should feel soft but not melted—think of the consistency of a thick cream. Creaming the butter and sugar together until the mixture is light and airy will incorporate air pockets, which contribute to that lovely rise in your cupcakes as they bake. If the butter is too cold or too warm, your cupcakes may turn out dense or overly oily.

Another key point during mixing is to avoid overworking the batter once you add the dry ingredients. Stirring just until combined will ensure that your cupcakes remain tender. If you overmix, the gluten develops too much, leading to a tough texture. When you scoop the batter into the muffin tin, aim for an even distribution to promote uniform baking.

Topping Tips

The caramelized topping of butter and brown sugar is what makes this recipe stand out. When melting these in the muffin tin, keep a close eye on them—watch for bubbling, which indicates they are just right. If they start to darken too quickly, this means the heat is too high, which could lead to burnt sugar. A well-controlled temperature allows for the right amount of caramelization, creating a beautifully gooey topping for your cupcakes.

If you can’t find fresh pineapple rings, canned pineapple is a great substitution. Just be sure to drain them well so the excess juice doesn't affect the batter or sog up the topping. Using fresh fruit adds a vibrant flavor, while canned offers convenience. Regardless of your choice, remember to place the pineapple rings and maraschino cherries carefully; they should sit nicely on top of the molten sugar without being submerged.

Ingredients

For the Cupcakes

1 cup all-purpose flour
1 tsp baking powder
1/2 tsp baking soda
1/4 tsp salt
1/2 cup unsalted butter, softened
1 cup granulated sugar
2 large eggs
1 tsp vanilla extract
1/2 cup buttermilk

For the Topping

1/4 cup unsalted butter
1/2 cup packed brown sugar
1 can of pineapple rings, drained
12 maraschino cherries

Instructions

Prepare the Topping

Preheat your oven to 350°F (175°C). In a muffin tin, melt the butter and brown sugar together until bubbly, approximately 5 minutes. Remove from oven and gently place a pineapple ring in each cup, adding a cherry in the center.

Make the Cupcake Batter

In a bowl, whisk together flour, baking powder, baking soda, and salt. In another bowl, cream the softened butter and granulated sugar until fluffy. Beat in the eggs one at a time, then add the vanilla and buttermilk, mixing well.

Combine and Bake

Gradually add the dry ingredients to the wet ingredients until just combined. Spoon the batter over the pineapple and cherries in the muffin tin, filling each cup about 2/3 full. Bake for 20 minutes or until a toothpick comes out clean.

Cool and Serve

Allow the cupcakes to cool in the tin for 5 minutes before inverting onto a serving plate. Enjoy warm or at room temperature for the best flavor.

Pro Tips

For an extra flavor boost, consider adding a pinch of cinnamon to the cupcake batter or garnishing with shredded coconut before baking.

Storage and Make-Ahead Tips

These Pineapple Upside Down Cupcakes can be made a day in advance. After baking, allow them to cool completely before storing them in an airtight container at room temperature. This helps maintain their moisture and keeps the topping from hardening. If you need to store them longer, consider refrigerating them, but be sure to bring them back to room temperature before serving to allow the flavors to bloom.

If you plan to freeze them, prepare the cupcakes without topping them. Once cooled, wrap them individually in plastic wrap, followed by a layer of foil. They can be frozen for up to three months. To serve, thaw them overnight in the fridge, then reheat in the microwave for a few seconds to refresh the texture.

Flavor Variations

To enhance the flavor profile of your cupcakes, consider adding spices like cinnamon or nutmeg to the batter. A half teaspoon of vanilla bean paste instead of traditional vanilla extract can add depth and elevate the taste. You may also try incorporating shredded coconut into the cupcake mix for an added tropical twist, which complements the pineapple beautifully.

If you're looking to switch things up even further, consider using a different fruit for the topping. Peaches, cherries, or pears can create delightful alternatives while adding their unique flavors. Just remember to adjust the cooking time slightly, as different fruits have varying moisture contents.

Questions About Recipes

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple gives a more vibrant flavor and better texture.

→ How do I store the leftovers?

Store in an airtight container at room temperature for up to 3 days.

→ Can I make the batter ahead of time?

It's best to bake the cupcakes right after mixing the batter for the fluffiest results.

→ What can I substitute for buttermilk?

You can use regular milk mixed with a tablespoon of vinegar as a buttermilk substitute.