Why You’ll Love This Recipe

These Pineapple Upside Down Cupcakes offer the familiar, comforting flavors of a classic pineapple upside-down cake but in a fun, individual-sized form. The caramelized pineapple and buttery brown sugar topping are perfectly paired with a soft and fluffy cupcake base. The small, portable size makes them ideal for parties, picnics, or any gathering where you want a tropical-inspired treat that’s both nostalgic and delicious. Plus, they’re simple to make and full of flavor, with the right balance of fruitiness and cake!

Ingredients

1/4 cup unsalted butter, melted
1/4 cup brown sugar, packed
12 pineapple rings (canned or fresh)
12 maraschino cherries
1 1/2 cups all-purpose flour
1/2 cup granulated sugar
1/4 tsp salt
2 tsp baking powder
1/2 cup milk
1/3 cup unsalted butter, softened
1 large egg
1 tsp vanilla extract

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

Directions

Preheat your oven to 350°F (175°C) and line a 12-cup muffin tin with paper liners. Alternatively, you can grease the muffin tin directly.
In a small bowl, mix together the melted butter and brown sugar. Spoon this mixture evenly into the bottom of each muffin cup.
Place one pineapple ring in each muffin cup over the sugar-butter mixture. If the pineapple rings are too large, you can cut them in half to fit. Place a maraschino cherry in the center of each pineapple ring.
In a medium bowl, whisk together the flour, granulated sugar, salt, and baking powder.
In a separate bowl, beat together the softened butter, milk, egg, and vanilla extract until smooth and well combined.
Gradually add the dry ingredients to the wet ingredients, mixing until just combined to form the cupcake batter.
Carefully spoon the batter into each muffin cup over the pineapple and cherry layer, filling each cup about 2/3 full.
Bake for 20-22 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
Remove from the oven and allow the cupcakes to cool in the tin for about 5 minutes. Then, run a knife around the edges of each cupcake to loosen it and invert them onto a serving platter.
Serve the cupcakes warm or at room temperature, garnished with additional pineapple if desired.

Servings and Timing

Servings: 12 cupcakes
Prep time: 15 minutes
Cook time: 20-22 minutes
Total time: 40-45 minutes

Variations

Coconut: Add 1/4 cup shredded coconut to the cupcake batter for a tropical twist. The coconut complements the pineapple flavor beautifully.
Spices: Add a pinch of cinnamon or nutmeg to the batter for a warm, spiced flavor that pairs well with the pineapple.
Caramel Drizzle: Drizzle some homemade caramel sauce over the finished cupcakes for an extra layer of sweetness and richness.
Other Fruit: Swap out the pineapple for other fruits like peaches, cherries, or apricots for a variation on the classic.
Gluten-Free: Use a gluten-free flour blend in place of all-purpose flour to make these cupcakes gluten-free while still maintaining their moist texture.

Storage/Reheating

Storage: Store leftover Pineapple Upside Down Cupcakes in an airtight container at room temperature for up to 2 days. If you want to keep them fresh longer, store them in the fridge for up to 4 days.
Freezing: These cupcakes freeze well! Once completely cooled, wrap them individually in plastic wrap and place them in a freezer-safe container. They can be frozen for up to 1 month. To serve, thaw at room temperature for 30 minutes.
Reheating: To reheat, place the cupcakes in the microwave for 10-15 seconds or warm them in a preheated oven at 300°F (150°C) for about 5 minutes.

FAQs

Can I use fresh pineapple instead of canned pineapple rings?

Yes! Fresh pineapple can be used instead of canned pineapple rings. Just slice the pineapple into rings or small chunks, ensuring they are about the same size as the canned rings to fit in the muffin cups.

How can I make these cupcakes more flavorful?

To enhance the flavor, you can add spices like cinnamon or ginger to the batter. A dash of rum or vanilla extract also gives the cupcakes a deeper flavor profile.

Can I make this recipe into one large cake instead of cupcakes?

Yes, you can bake this recipe as a single cake in a greased 9-inch round or square cake pan. The baking time will be about 35-40 minutes, depending on the size and depth of the pan.

Can I substitute the maraschino cherries with another fruit?

Yes, you can substitute maraschino cherries with other fruits like fresh cherries, diced strawberries, or even other small, tropical fruits for a variation.

Can I make these cupcakes dairy-free?

To make the cupcakes dairy-free, substitute the butter with a dairy-free butter or margarine and use a plant-based milk like almond milk or coconut milk.

How do I prevent the cupcakes from sticking to the pan?

Be sure to grease the muffin tin thoroughly or use paper liners to prevent the cupcakes from sticking. You can also line the bottom of each muffin cup with parchment paper for extra assurance.

How do I know when the cupcakes are done?

The cupcakes are done when a toothpick inserted into the center comes out clean or with a few moist crumbs. If it comes out with wet batter, give them a few more minutes in the oven.

Can I make these cupcakes in advance?

Yes, you can make the cupcakes a day ahead. Just store them in an airtight container and refrigerate them. Allow them to come to room temperature or warm them slightly before serving.

Can I add frosting to these cupcakes?

While these cupcakes are delicious on their own, you can certainly add frosting. A cream cheese frosting would pair wonderfully with the tropical pineapple flavors.

Can I make these cupcakes gluten-free?

Yes, you can make these cupcakes gluten-free by using a gluten-free flour blend instead of all-purpose flour. Just be sure to check the other ingredients, such as baking powder, to ensure they are gluten-free as well.

Conclusion

Pineapple Upside Down Cupcakes are a delightful twist on a classic dessert, offering a perfect balance of sweet, tangy pineapple and a moist, fluffy cupcake base. These mini treats are simple to make, easy to serve, and perfect for any occasion that calls for a tropical-inspired dessert. Whether you’re making them for a special gathering or just to satisfy your sweet tooth, these cupcakes are sure to be a crowd favorite!

Pineapple Upside Down Cupcakes