Delicious Pineapple Upside Down Cupcakes: A Tropical Treat for Your Sweet Tooth

Introduction: Welcome to a tropical twist on a classic favorite! These Pineapple Upside Down Cupcakes are a delightful blend of sweet pineapple, tangy cherries, and moist cake. Whether you’re hosting a party or simply craving a taste of paradise, these cupcakes are sure to impress.

Prep Time: 15 minutes
Cook Time: 25 minutes
Total Time: 40 minutes
Servings: 24 cupcakes


  • Cooking spray
  • 1/2 cup melted butter
  • 1 1/2 cups brown sugar
  • 24 maraschino cherries
  • 1 (20 ounce) can crushed pineapple, drained
  • 1 (18.25 ounce) package pineapple cake mix (such as Duncan Hines® Pineapple Supreme)
  • 3 eggs
  • 1 1/3 cups pineapple juice
  • 1/3 cup vegetable oil
  • 1 tablespoon confectioners’ sugar for dusting (optional)

Step-by-Step Guide:

  1. Preparation: Preheat your oven to 350°F (175°C). Generously spray two 12-cup muffin tins with cooking spray.
  2. Creating the Base: In each muffin cup, place a teaspoon of melted butter, followed by a tablespoon of brown sugar. Add a maraschino cherry in the center and surround it with crushed pineapple.
  3. Mixing the Batter: In a large bowl, combine the pineapple cake mix, eggs, pineapple juice, and vegetable oil. Mix until the batter is smooth and free of lumps.
  4. Assembling the Cupcakes: Pour the batter over the pineapple and cherry base in each muffin cup, filling them about three-quarters full.
  5. Baking Time: Bake in the preheated oven for about 25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
  6. Finishing Touch: Allow the cupcakes to cool for a few minutes, then carefully invert them onto a serving tray. Dust with confectioners’ sugar for an extra touch of sweetness, if desired.

Nutritional Information: Each serving of these Pineapple Upside Down Cupcakes is a delightful treat. While indulging, remember that moderation is key in maintaining a balanced diet.

Tips for Success:

  • Quality Ingredients: Choose high-quality ingredients for the best flavor.
  • Butter and Brown Sugar Ratio: Achieve the perfect caramelized topping by getting the ratio of butter to brown sugar just right.
  • Pineapple Placement: Arrange the pineapple and cherries in a visually appealing pattern for a stunning presentation.
  • Even Baking: Ensure your oven is properly preheated and bake the cupcakes in the middle rack for even cooking.
  • Don’t Overmix the Batter: Mix the batter just until the ingredients are combined to avoid tough cupcakes.
  • Moisture Content: Drain the crushed pineapple well, but don’t squeeze out all the juice for the perfect texture.
  • Cooling Time: Allow the cupcakes to cool for just a few minutes before inverting them onto a plate.
  • Use the Right Tools: A scoop can help you evenly distribute the batter, and a thin knife or spatula can help loosen the edges when inverting the cupcakes.

Serving Suggestions:

  • Classic Whipped Cream: Add a dollop of freshly whipped cream for a creamy texture.
  • Vanilla Ice Cream: Serve warm with a scoop of vanilla ice cream for a classic pairing.
  • Coconut Shavings: Sprinkle toasted coconut shavings for a tropical twist and added crunch.
  • Pineapple Sauce: Drizzle with a simple pineapple sauce for extra moisture and flavor.
  • Rum Glaze: Brush warm cupcakes with a rum glaze for an adult twist.
  • Fresh Fruit Salad: Serve with a side of fresh tropical fruit salad for a refreshing contrast.
  • Dessert Coffee Pairing: Pair with a dessert coffee for a delightful combination of flavors.
  • Caramel Drizzle: Drizzle with caramel sauce for added indulgence.
  • Mint Garnish: Add a sprig of fresh mint for a pop of color.
  • Powdered Sugar Dusting: Dust with powdered sugar for an elegant finish.


  • Can I make these cupcakes in advance? Yes, bake a day in advance and store in an airtight container at room temperature.
  • Can I use fresh pineapple instead of canned? Yes, use finely chopped fresh pineapple.
  • How do I store leftover cupcakes? Store in an airtight container at room temperature or refrigerate.
  • Can I freeze Pineapple Upside Down Cupcakes? Yes, wrap individually and freeze for up to 3 months.
  • Is it possible to make this recipe gluten-free? Yes, use a gluten-free cake mix and ensure all ingredients are gluten-free.
  • Can I make a vegan version? Yes, use vegan cake mix and egg substitutes.
  • How do I know when the cupcakes are done? Insert a toothpick into the center; it should come out clean.
  • Why did my cupcakes stick to the pan? Ensure the pan is well-greased and allow to cool slightly before inverting.
  • Can I make this in a cake form? Yes, adjust baking time accordingly.
  • What can I use instead of maraschino cherries? Use fresh pitted cherries or omit.
  • Keto Pineapple Upside Down Cupcakes Recipe: See adapted keto-friendly recipe for a low-carb alternative.

Conclusion: These Pineapple Upside Down Cupcakes are a delightful treat for any occasion. With their tropical flavor and stunning presentation, they’re sure to be a hit with family and friends. Enjoy the taste of paradise with every bite!

Credit: Recipes Need

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