Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes are the perfect miniature version of the classic cake with buttery yellow cake, pineapple chunks, and cherries.

This amazing miniature Cake Recipe is the perfect cupcake version of Pineapple Upside Down Cake. Making them into cupcakes makes this classic pineapple dessert easy to serve to a crowd without worrying about slicing the cake into pieces. 

Pineapple Upside Down Cupcakes on serving plate

This recipe takes an iconic dessert and makes them into adorable cupcakes that are the perfect addition to any celebratory dessert table. Bright red and yellow colors from the fruit make the cakes look amazing, and are sure to bring a smile to everyone’s face. 

The sweet and tangy cherry and pineapple flavors go perfectly with the moist yellow cake recipe. The refreshing flavors are the perfect way to end a Summer BBQ or just enjoy it on a hot day. Serve each cake up with a scoop of Vanilla Ice Cream to make the dessert nice and cooling. 

Just like the classic cake, they have a pineapple and cherry layer that’s baked on the bottom but served on top. To accomplish this in the mini version, you simply add the pineapple and cherry topping to the bottom of each muffin cup, then pour the cake batter over top. Once the pineapple cupcakes are baked, simply flip them over to reveal the beautiful fruit topping ready to serve.

Pineapple Upside Down Cupcakes collage

MORE PINEAPPLE DESSERTS

BAKING TIPS

  • Prep time: Preheat the oven to 350 degrees. Then spray a 12-cup muffin tin with nonstick cooking spray. You want to use nonstick spray instead of paper liners so that the cupcakes will easily come out with the pineapple topping. 
  • Topping: Melt the butter and brown sugar in a microwave-safe bowl. Mix the ingredients together and divide it evenly into the muffin cups. Add the pineapple pieces on top, then place cherries in the middle of the pineapples. 
  • Cake batter: Add the butter, granulated sugar, and brown sugar to your electric stand mixer. Mix for 1-2 minutes until light and fluffy. Then add in the egg, vanilla extract, sour cream, and pineapple juice. Turn the electric mixer to low speed until combined. Then sift in the flour, baking powder, and salt. Mix at low speed again until just combined. 
  • Baking time: Spoon the batter from the bowl into the muffin cups over the sliced pineapple. Pop the pan in the preheated oven to bake for 20-22 minutes. Keep the cupcakes in the oven until a toothpick inserted in the center of one comes out clean. Let the cupcakes cool down for 10 minutes while still in the tin. After 10 minutes run a knife around the edge of each cake to loosen them up. Then put a baking sheet on top of the muffin tin, and flip it over so the cupcakes come out with the pineapple slices on top. 
Pineapple Upside Down Cupcakes on cooling rack

VARIATIONS

  • Pineapple rings: Instead of using diced pineapple in the pineapple layer, you can use whole pineapple slices. Put a slice of pineapple at the base of each muffin cup and then put a cherry in the center for a cherry-filled pineapple ring. 
  • Yellow cake mix: Instead of fully making a cake from scratch, you can save time by using a boxed cake mix. To make the boxed cake mix wonderfully moist, add one extra egg to what the back of the box said. You should also exchange the water with milk and the oil with melted butter. 
  • Coconut: Coconut and pineapple make a wonderful tropical flavor together. To incorporate that into this dessert, sprinkle coconut flakes into the pineapple topping. 
  • Different fruits: For some variations in the fruit topping, you can try using different kinds of berries like cranberries, strawberries, or raspberries. 
Pineapple Upside Down Cupcakes on serving plate

MORE CUPCAKE RECIPES

HOW TO STORE

  • Serve: After cooking, you don’t want to leave the Pineapple Cupcakes at room temperature for more than 2 hours. 
  • Store: Cover the cupcakes or put them in an airtight container to store in the fridge for up to 5 days. 
  • Freeze: You can also freeze the pineapple cakes for up to 1 month as long as their kept sealed. Take them out of the freezer and let them thaw in the fridge for a few hours before dessert time. 

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Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes are the perfect miniature version of the classic cake with buttery yellow cake, pineapple chunks, and cherries.
Yield 12 Servings
Prep Time 10 minutes
Cook Time 20 minutes
Total Time 40 minutes
Course Dessert
Cuisine American
Author Sabrina Snyder

Ingredients
 

  • 3 tablespoons unsalted butter , melted
  • 1/2 cup brown sugar , packed
  • 20 ounces pineapple chunks in juice , drained (reserve ¼ cup of juice for cake)
  • 12 maraschino cherries , stems removed
  • 1 1/3 cups flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon kosher salt
  • 1/4 cup unsalted butter , softened
  • 1/2 cup sugar
  • 1/4 cup packed brown sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1/4 cup sour cream

Instructions

  • Preheat the oven to 350 degrees.
  • Spray a 12 cup muffin tin with baking spray.
  • Melt the butter and brown sugar in a microwave-safe bowl then mix together and pour into the muffin tins.
  • Add pineapple chunks to the bottom of muffin tins then place cherries in the middle of the circles.
  • To your stand mixer add butter, sugar, and brown sugar on medium speed until light and fluffy, for 1-2 minutes.
  • Add in the egg, vanilla extract, sour cream, and pineapple juice at low speed until combined.
  • Sift together flour, baking powder and salt then add it into the stand mixer on low speed until just combined.
  • Spoon batter carefully into muffin tin until ¾ full.
  • Bake for 20-22 minutes or until a toothpick comes out clean.
  • Let cool for 10 minutes.
  • Place baking sheet upside down on muffin tin and flip over quickly while still warm.

Nutrition

Calories: 247kcal | Carbohydrates: 42g | Protein: 2g | Fat: 8g | Saturated Fat: 5g | Trans Fat: 1g | Cholesterol: 36mg | Sodium: 113mg | Potassium: 142mg | Fiber: 1g | Sugar: 31g | Vitamin A: 284IU | Vitamin C: 4mg | Calcium: 48mg | Iron: 1mg
Keyword: Pineapple Upside Down Cupcakes
Pineapple Upside Down Cupcakes collage

About the Author: Sabrina Snyder

Sabrina is a professionally trained Private Chef of over 10 years with ServSafe Manager certification in food safety. She creates all the recipes here on Dinner, then Dessert, fueled in no small part by her love for bacon.

Sabrina Snyder is a professionally trained personal and private chef of over 10 years who is the creator and developer of all the recipes on Dinner, then Dessert.

She is also the author of the upcoming cookbook: Dinner, then Dessert – Satisfying Meals Using Only 3, 5 or 7 Ingredients which is being published by Harper Collins.

She started Dinner, then Dessert as a business in her office as a lunch service for her coworkers who admired her lunches before going to culinary school and becoming a full time personal chef and private chef.

As a personal chef Sabrina would cook for families one day a week and cook their entire week of dinners. All grocery shopping, cooking and cleaning was done along with instructions on reheating. As a private chef she cooked for private parties and cooked in family homes in the evenings for families on a nightly basis after working as a personal chef during the day.

Sabrina has been certified as a ServSafe Manager since 2007 and was a longstanding member of the USPCA Personal Chef Association including being on the board of the Washington DC Chapter of Chefs in the US Personal Chef Association when they won Chapter of the year.

As a member of the community of food website creators Sabrina Snyder has spoken at many conferences regarding her experiences as a food writer including the Indulge Food Conference, Everything Food Conference, Haven Food Conference and IACP Annual Food Professionals Conference.

Sabrina lives with her family in sunny California.

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