Pineapple Upside Down Cupcakes

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Pineapple Upside Down Cupcakes – A Mini Twist on a Classic Favorite

There’s something undeniably charming about pineapple upside down cake. With its caramelized brown sugar topping, juicy pineapple, and bright red cherry center, it’s a dessert that’s as beautiful as it is delicious. But when you shrink it down into cupcake form? Pure magic. These Pineapple Upside Down Cupcakes are the perfect bite-sized version of the retro classic—easy to serve, fun to eat, and guaranteed to impress.

Whether you’re baking for a summer picnic, a holiday potluck, or just a sweet treat to brighten your day, these cupcakes are a tropical escape in every bite.

Why You’ll Love These Cupcakes

  • Individual servings – No slicing or mess—just grab and go.
  • Caramelized topping – Buttery brown sugar melts into the fruit for a sticky-sweet finish.
  • Tropical flavor – Pineapple and cherry bring sunshine to every bite.
  • Easy to make – Uses simple ingredients and a standard muffin tin.
  • Perfect for parties – A crowd-pleasing dessert that travels well.

Ingredients

This recipe makes 12 cupcakes.

For the Topping

  • ¼ cup unsalted butter, melted
  • ½ cup brown sugar, packed
  • 12 maraschino cherries, halved
  • 1 cup pineapple chunks or crushed pineapple, well drained

For the Cake Batter

You can use your favorite yellow cake mix (prepared according to package directions) or make a simple homemade batter:

  • 1 cup all-purpose flour
  • ½ cup granulated sugar
  • 1½ teaspoons baking powder
  • ¼ teaspoon salt
  • ½ cup milk
  • ¼ cup vegetable oil
  • 1 large egg
  • 1 teaspoon vanilla extract

Tip: If using a cake mix, prepare the batter as directed and skip the homemade batter section.

Equipment You’ll Need

  • 12-cup muffin tin
  • Cupcake liners (optional)
  • Mixing bowls
  • Whisk and spatula
  • Measuring cups and spoons
  • Spoon or cookie scoop
  • Cooling rack

Step-by-Step Instructions

Step 1: Preheat and Prep

Preheat your oven to 350°F (175°C).

Grease a 12-cup muffin tin generously with butter or nonstick spray. You can use cupcake liners, but the topping may stick—greasing the pan directly works best.

Step 2: Make the Topping

In a small bowl, combine:

  • ¼ cup melted butter
  • ½ cup brown sugar

Stir until well mixed.

Spoon about 1 tablespoon of the mixture into the bottom of each muffin cup.

Add:

  • 1–2 pineapple chunks or 1 tablespoon crushed pineapple
  • 1 cherry half, cut side up

Press gently to flatten the fruit into the sugar mixture.

Step 3: Make the Cake Batter (If Not Using a Mix)

In a medium bowl, whisk together:

  • 1 cup flour
  • ½ cup sugar
  • 1½ teaspoons baking powder
  • ¼ teaspoon salt

In another bowl, whisk together:

  • ½ cup milk
  • ¼ cup oil
  • 1 egg
  • 1 teaspoon vanilla

Pour the wet ingredients into the dry and stir until just combined—don’t overmix.

Step 4: Assemble the Cupcakes

Spoon the batter over the fruit mixture in each muffin cup, filling about ¾ full.

Tap the pan gently on the counter to remove air bubbles and level the batter.

Step 5: Bake

Bake at 350°F (175°C) for 20–25 minutes, or until a toothpick inserted into the center comes out clean.

Let the cupcakes cool in the pan for 5 minutes.

Step 6: Invert and Cool

Place a cooling rack or tray over the muffin tin.

Carefully invert the pan to release the cupcakes—use a knife to loosen edges if needed.

Let cool completely before serving.

Tip: Serve warm with a scoop of vanilla ice cream for extra indulgence.

Time & Yield

  • Prep Time: 15 minutes
  • Bake Time: 20–25 minutes
  • Total Time: ~40 minutes
  • Yield: 12 cupcakes
  • Calories: ~220 kcal per cupcake (approximate)

Tips for Success

  • Drain the pineapple well to avoid soggy bottoms.
  • Use a nonstick muffin tin and grease thoroughly for easy release.
  • Invert while warm—waiting too long may cause the topping to stick.
  • Don’t overfill—leave room for the batter to rise.
  • Store leftovers in an airtight container at room temperature for up to 2 days or refrigerate for up to 5.

Variations to Try

  • Mini Cupcakes: Use a mini muffin tin and adjust bake time to 10–12 minutes.
  • Spiced Version: Add ½ teaspoon cinnamon or ginger to the batter.
  • Coconut Twist: Sprinkle shredded coconut over the topping before baking.
  • Rum-Infused: Add 1 tablespoon dark rum to the batter for a tropical kick.
  • Gluten-Free: Use a 1:1 gluten-free flour blend.

Perfect For…

  • Summer BBQs and picnics
  • Holiday dessert trays
  • Potlucks and bake sales
  • Afternoon tea
  • Just-because baking days

Final Thoughts

These Pineapple Upside Down Cupcakes are a delightful twist on a beloved classic—sweet, sticky, and bursting with tropical flavor. They’re easy to make, fun to serve, and guaranteed to bring a little sunshine to your dessert table. Whether you’re baking for a crowd or just treating yourself, this recipe is a keeper.

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