Pineapple Upside-Down Cupcakes

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These pineapple upside-down cupcakes are delicious mini versions of the cake! After flipping, a layer of sweet brown sugar caramelized pineapple ends up on top of a lightly spiced vanilla cupcake. Top the inverted cupcakes with whipped cream and a maraschino cherry to make them extra cute!

pineapple upside-down cupcakes topped with whipped cream and maraschino cherries

In cupcakes with pineapple, like my hummingbird cupcakes and my piña colada cupcakes, the pineapple flavor can be overpowered by other more prominent flavors like banana and coconut. Here, by having chunks of pineapple on the top of the cupcakes, the pineapple becomes the star!

Baking Tips

Make the caramel first. This recipe calls for an easy-to-make brown sugar caramel with sugar, brown sugar, butter, and, if you’d like, a splash of dark rum.

Caramel ingredients in a pot
Then, divide the caramel evenly between greased cupcake liners. It’s important to grease the liners so that the the cupcakes come out cleanly.

Adding caramel to cupcake liners

Next, place pineapple pieces onto the caramel. You can use:

  • fresh pineapple cut into small chunks,
  • canned pineapple tidbits, or
  • pineapple rings.

Whatever you use, make sure the pineapple is nice and dry (I wrap it in paper towels and pat it gently). You don’t want any extra moisture getting into the batter.

Adding pineapple to cupcake liners

Finally, top the pineapple pieces with cupcake batter filled almost all the way to the tops of the cupcake liners.

Adding batter to pineapple-upside down cupcakes
When the pineapple cupcakes come out of the oven, let them cool in the cupcake tins. Then, carefully take them out of the liners and flip them over.

pineapple upside-down cupcake without whipped cream
Just before serving, top with whipped cream (chantilly cream) and a maraschino cherry!

close-up view of a pineapple upside-down cupcake topped with whipped cream and a maraschino cherry


In addition to topping with a cherry, you can also try garnishing the cupcakes with candied pineapple. It’s so sweet and delicious!

Candied pineapple on parchment
For a more grown-up version, increase the splash of rum in the caramel sauce to a more substantial 3 tablespoons and top with a boozy Luxardo cherry instead of the kid-friendly cherries.

You can also experiment with using other fruit. Try making peach upside-down cupcakes like you see in this peach upside-down cake. Or, consider cupcake versions of apple upside-down cake or cranberry upside-down cake.

I’ve also made a fantastic Jamaican rum cake that would pair well with these cupcakes.

Finally, if you’re a huge pineapple fan, try my pineapple bars!

Did you make this recipe? Leave a review!
pineapple upside-down cupcakes topped with whipped cream and maraschino cherries
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5 from 2 votes

Pineapple Upside-Down Cupcakes

Pineapple upside-down cupcakes are delicious mini pineapple upside-down cakes! Caramelized pineapple tops sweet spiced cupcakes.
Course Dessert
Cuisine American
Prep Time 15 minutes
Cook Time 25 minutes
Cooling Time 20 minutes
Total Time 1 hour
Servings 14
Calories 256kcal
Author Stefani


Caramel Ingredients

  • 1/3 cup granulated sugar
  • 1/3 cup brown sugar
  • 6 tablespoons unsalted butter
  • 1 tablespoon dark rum optional

Cupcake Ingredients

  • 10 ounces pineapple tidbits in pineapple juice 1 can
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/4 teaspoon ground cardamom
  • 1/2 teaspoon ground cinnamon
  • 1/2 cup unsalted butter room temperature
  • 1/2 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup pineapple juice reserved from the can of pineapple
  • 1/4 cup milk
  • chantilly cream or any sweetened whipped cream to taste
  • 14 maraschino cherries


Caramel Instructions

  • Melt all caramel ingredients on medium-low heat in a small saucepan, stirring periodically until fully melted and combined - about five minutes.
  • Distribute evenly between greased cupcake liners, about 2 tablespoons per liner.

Cupcake Instructions

  • Preheat oven to 350 F.
  • Drain can of pineapple tidbits, reserving liquid.
  • Remove extra moisture from the pineapple chunks by gently pressing them between paper towels.
  • Place about 1 tablespoon of pineapple on top of the caramel in each liner. There will be pineapple left over. You can use it decorate the cupcakes or just eat it!
  • In a medium-sized mixing bowl, whisk together flour, baking powder, salt, cardamom, and cinnamon. Set aside.
  • In another medium-sized mixing bowl or the bowl of a stand mixed, cream butter and sugar until light and fluffy.
  • Mix in eggs, one at a time.
  • Mix in vanilla extract.
  • Mix in dry ingredients until just combined.
  • Mix in pineapple juice and milk.
  • Divide batter evenly over the pineapple in each liner, filling the liners almost all the way to the tops.
  • Bake for 20 minutes or until a toothpick comes out of the center of a cupcake dry. The cupcakes may have some bubbles on the top from the caramel boiling up. The tops will become the bottoms when inverted so this doesn't matter.
  • Let the cupcakes cool in the cupcake tins, about 15 minutes.
  • Once cool, remove the cupcakes from the tins, remove the liners, and carefully invert the cupcakes.
  • Top each cupcake with chantilly cream and a maraschino cherry.


Store at room temperature in an air-tight container for up to three days.
For a more grown-up version, increase the splash of rum in the caramel sauce to a more substantial 3 tablespoons and top with a boozy Luxardo cherry instead of the kid-friendly cherries.


Calories: 256kcal | Carbohydrates: 34g | Protein: 3g | Fat: 12g | Saturated Fat: 8g | Cholesterol: 54mg | Sodium: 98mg | Potassium: 115mg | Fiber: 1g | Sugar: 23g | Vitamin A: 404IU | Vitamin C: 3mg | Calcium: 44mg | Iron: 1mg
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