Name: Pineapple Upside Down Cupcakes
Prep time: 15 min
Cook time: PT-485830H17M2S
Total time: 40 min
Cuisine: American
Ingredients: Pineapple slices (canned or fresh) – 12 slices; Maraschino cherries – 12; Brown sugar – 1/2 cup; Butter – 1/4 cup (melted, plus extra for topping); All-purpose flour – 1 1/2 cups; Baking powder – 1 1/2 tsp; Salt – 1/4 tsp; Granulated sugar – 3/4 cup; Eggs – 2 large; Milk – 1/2 cup; Vanilla extract – 1 tsp

Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert. These individual-sized treats combine caramelized pineapple rings, maraschino cherries, and a moist, buttery cake that bakes right on top. They’re perfect for parties, gatherings, or anytime I want a nostalgic, tropical-flavored sweet treat .

Why You’ll Love This Recipe

I love this recipe because it takes the charm of a traditional pineapple upside down cake and makes it perfectly portioned for any occasion. The cupcakes have a beautiful caramelized topping that’s both sweet and tangy, and the cake itself stays moist and tender. They’re easy to make, visually stunning, and always a crowd-pleaser.

Ingredients

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

Pineapple slices (canned or fresh)
Maraschino cherries
Brown sugar
Butter
All-purpose flour
Baking powder
Salt
Granulated sugar
Eggs
Milk
Vanilla extract

Directions

Preheat the oven to 350°F (175°C) and prepare a muffin tin by greasing it or lining it with cupcake liners.
In a small saucepan, melt butter and stir in brown sugar until combined and bubbly. Spoon a little of this mixture into each muffin cup.
Place a pineapple slice and a maraschino cherry in each muffin cup on top of the brown sugar mixture.
In a mixing bowl, whisk together flour, baking powder, and salt.
In another bowl, beat together granulated sugar, eggs, milk, melted butter, and vanilla extract until smooth.
Gradually add the dry ingredients to the wet ingredients, mixing gently until just combined.
Spoon the batter evenly over the pineapple and cherry in each muffin cup.
Bake for 20-25 minutes or until a toothpick inserted into the center comes out clean.
Allow cupcakes to cool for 5 minutes, then invert onto a serving plate so the pineapple topping is visible.

Servings and Timing

This recipe makes about 12 cupcakes. Preparation time is around 15 minutes, and baking takes approximately 20-25 minutes. Overall, I can have these ready in about 40 minutes.

Variations

I sometimes like to add a sprinkle of cinnamon to the brown sugar mixture for extra warmth. Another variation I enjoy is swapping the maraschino cherries for fresh raspberries or blueberries for a slightly different fruity twist. For a richer cake, I might substitute some of the milk with coconut milk to enhance the tropical flavor.

Storage/Reheating

I keep these cupcakes stored in an airtight container at room temperature for up to 2 days. If I want to keep them longer, I refrigerate them for up to 5 days. To reheat, I gently warm them in the microwave for about 10-15 seconds to bring back that soft texture without drying out the cake.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works great! I cut it into rings or small pieces and cook them slightly if needed to soften before adding to the cupcakes.

Can these cupcakes be made gluten-free?

Absolutely. I substitute the all-purpose flour with a gluten-free flour blend that works well for baking.

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

Greasing the muffin tin well or using silicone liners helps a lot. Also, letting the cupcakes cool briefly before flipping them ensures the topping stays intact.

Can I make this recipe dairy-free?

Yes, I use dairy-free butter and plant-based milk like almond or coconut milk as substitutes.

How long can I freeze these cupcakes?

I freeze them in an airtight container for up to 2 months. When ready, I thaw them overnight in the fridge and warm slightly before serving.

Conclusion

Pineapple Upside Down Cupcakes are a fun and tasty way to enjoy a classic dessert in a new format. I love how easy they are to make and how impressive they look when served. Whether for a casual snack or a special occasion, they bring a lovely tropical sweetness that’s sure to please everyone.