I bring you a delightful twist on a classic dessert—Pineapple Upside Down Cupcakes. These individual treats capture the essence of the traditional cake, featuring caramelized brown sugar, juicy pineapple rings, and a moist, buttery crumb. Perfect for any occasion, they offer a nostalgic taste in a convenient, single-serving form.

Why You’ll Love This Recipe

Perfect Portions: I find these cupcakes ideal for serving—no slicing required.
Tropical Touch: The pineapple adds natural sweetness and moisture that I adore.
Quick Bakes: I appreciate that they're ready from bowl to oven in under 30 minutes.
No Fancy Tools Needed: I only need a muffin tin and canned pineapple—simple and pantry-friendly.
Freezer-Friendly: I can make them ahead and freeze; they reheat beautifully.

Ingredients

(Here's a tip: Check out the full list of ingredients and measurements in the recipe card below.)

For the Topping:

¼ cup unsalted butter, melted
½ cup light brown sugar
4–5 canned pineapple rings, drained
12 maraschino cherries

For the Cake Batter:

1 cup all-purpose flour
¾ cup granulated sugar
1 teaspoon baking powder
½ teaspoon salt
¼ cup vegetable oil
1 large egg, lightly beaten
½ cup milk
¼ cup pineapple juice (reserved from the canned pineapple)

Directions

Preheat Oven & Prepare Muffin Tin: I preheat my oven to 350°F (175°C) and grease a 12-cup muffin tin with cooking spray or butter.
Make the Caramelized Topping: In a small bowl, I mix the melted butter and brown sugar. I spoon about 1 tablespoon of this mixture into each muffin cup, then place a pineapple ring and a maraschino cherry in the center.
Mix the Cake Batter: In a mixing bowl, I whisk together the flour, granulated sugar, baking powder, and salt. In another bowl, I combine the vegetable oil, egg, milk, and pineapple juice. I then gradually add the dry ingredients to the wet, stirring gently until just combined.
Fill & Bake the Cupcakes: I fill each muffin cup two-thirds full with the batter, ensuring not to overflow the pineapple layer. I bake them for 20–25 minutes, or until a toothpick inserted comes out clean.
Cool & Serve: After baking, I let the cupcakes cool in the pan for 5 minutes, then carefully invert them onto a wire rack to cool completely. I enjoy them warm or at room temperature.

Servings and Timing

Servings: 12 cupcakes
Prep Time: 15 minutes
Cook Time: 20–25 minutes
Total Time: 35–40 minutes

Variations

Coconut Twist: I add ½ cup of shredded coconut to the batter for a tropical flair.
Rum-Infused: For an adult version, I mix a tablespoon of dark rum into the butter and brown sugar topping.
Mini Cupcakes: Using a mini muffin tin, I make bite-sized versions and reduce the baking time to 12–15 minutes.
Nutty Addition: I sprinkle chopped pecans or walnuts over the brown sugar before adding the pineapple for added crunch.

Storage/Reheating

Storage: I store the cooled cupcakes in an airtight container at room temperature for up to 2 days or refrigerate for up to 5 days.
Freezing: I freeze them individually wrapped for up to 3 months. To reheat, I thaw at room temperature and warm in the microwave for 10–15 seconds.

FAQs

What type of pineapple is best for this recipe?

I prefer using canned pineapple rings for uniformity and ease, but fresh pineapple slices can also be used if I cut them to fit the muffin cups.

Can I use a different type of flour?

Yes, I can substitute all-purpose flour with a gluten-free blend if needed, though the texture may vary slightly.

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

I ensure to grease the muffin tin thoroughly and let the cupcakes cool for 5 minutes before inverting them onto a wire rack.

Can I make these cupcakes ahead of time?

Absolutely, I often bake them a day in advance and store them in an airtight container. They taste just as delicious the next day.

Is it necessary to use maraschino cherries?

While not essential, I find that maraschino cherries add a classic touch and a pop of color. I can omit them or substitute with another fruit if I prefer.

Conclusion

I find Pineapple Upside Down Cupcakes to be a delightful and convenient way to enjoy a classic dessert. Their individual servings make them perfect for gatherings, and the combination of caramelized pineapple and moist cake is simply irresistible. I hope you enjoy baking and savoring these tropical treats as much as I do.

Pineapple Upside Down Cupcakes

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Author: Sue
Prep Time: 15 minutes
Cook Time: 25 minutes
Total Time: 40 minutes
Yield: 12 cupcakes
Category: Dessert
Method: Baking
Cuisine: American
Diet: Vegetarian

Print Recipe

Description

Pineapple Upside Down Cupcakes are a delightful twist on the classic cake, featuring caramelized brown sugar, juicy pineapple, and moist cake in individual servings—perfect for any occasion.

Instructions

Preheat oven to 350°F (175°C) and grease a 12-cup muffin tin.
Mix melted butter and brown sugar in a small bowl. Spoon 1 tablespoon into each muffin cup. Place a pineapple ring and a maraschino cherry in the center.
In a bowl, whisk flour, granulated sugar, baking powder, and salt. In another bowl, combine vegetable oil, egg, milk, and pineapple juice.
Gradually mix dry ingredients into the wet until just combined.
Fill muffin cups two-thirds full with batter. Bake for 20–25 minutes or until a toothpick inserted comes out clean.
Cool in pan for 5 minutes, then invert onto a wire rack to cool completely.