Pineapple Upside Down Cupcakes
These Pineapple Upside Down Cupcakes are a delightful treat that combines the nostalgic flavors of a classic dessert with the fun of individual servings. Perfect for parties, picnics, or simply as a sweet indulgence at home, these cupcakes stand out with their moist texture and vibrant toppings. The caramelized pineapple and bright cherry create a festive look that is sure to impress your guests.
Why You’ll Love This Recipe
- Easy to Make: With simple steps and common ingredients, these cupcakes are perfect for bakers of all skill levels.
- Versatile Treat: Great for birthdays, holiday gatherings, or just when you crave something sweet!
- Tropical Flavor: The combination of pineapple and brown sugar brings a taste of the tropics to your dessert table.
- Individual Servings: Perfectly portioned, each cupcake is easy to serve and even easier to enjoy.
Tools and Preparation
To make these Pineapple Upside Down Cupcakes, you’ll need a few essential tools. Having the right equipment will streamline your baking process.
Essential Tools and Equipment
- Muffin tin
- Nonstick spray or cupcake liners
- Mixing bowls
- Whisk
- Measuring cups and spoons
Importance of Each Tool
- Muffin tin: Creates perfectly shaped cupcakes that hold their form during baking.
- Mixing bowls: Essential for combining ingredients without spills, making cleanup easier.
- Whisk: Helps incorporate air into the batter for lighter cupcakes.

Ingredients
For the topping:
- ½ cup butter, melted
- ½ cup packed brown sugar
- 1 can (20 ounces) pineapple slices or chunks with juice, divided
- 21 maraschino cherries, stemless
For the cupcakes:
- 2 cups all-purpose flour
- 2 teaspoons baking powder
- ½ teaspoon salt
- ½ teaspoon baking soda
- ¼ cup canola oil
- ¾ cup granulated sugar
- 2 large eggs, room temperature
How to Make Pineapple Upside Down Cupcakes
Step 1: Preheat the Oven
Preheat the oven to 350°F (175°C). Prepare 21 muffin cups with nonstick spray or liners.
Step 2: Prepare the Topping
- Cut the pineapple into small ½-inch pieces.
- Place 1 teaspoon of melted butter into each muffin cup.
- Sprinkle 1 teaspoon of brown sugar on top of the butter.
- Arrange 4 pineapple pieces in a flower or cross shape inside each cup.
- Place a maraschino cherry in the center of each arrangement. Set aside.
Step 3: Make the Batter
- In a small bowl, whisk together flour, baking powder, salt, and baking soda.
- In a large bowl, whisk together canola oil and granulated sugar until combined.
- Beat in eggs until just mixed.
Step 4: Combine Ingredients
Fold the dry ingredients into the wet ingredients gently. When the batter thickens, add reserved pineapple juice. Stir until smooth.
Step 5: Assemble Cupcakes
Spoon about 2 tablespoons of batter into each muffin cup, filling almost to the top.
Step 6: Bake
Bake for 15–17 minutes or until golden brown and a toothpick inserted into the center comes out clean.
Step 7: Cool and Invert
Let cupcakes cool in the pan for 30 minutes. Run a thin knife around the edges, then carefully invert onto a cooling rack so that the pineapple and cherry are on top. Serve warm or at room temperature.
How to Serve Pineapple Upside Down Cupcakes
These Pineapple Upside Down Cupcakes are delightful and versatile, making them perfect for a variety of occasions. Whether you’re hosting a party or enjoying a casual dessert at home, consider these serving suggestions to elevate your experience.
Fun Serving Suggestions
- With Whipped Cream: Top each cupcake with a dollop of whipped cream for extra creaminess.
- A Scoop of Ice Cream: Pair warm cupcakes with a scoop of vanilla or coconut ice cream for a refreshing contrast.
- Tropical Fruit Salad: Serve alongside a light tropical fruit salad for a fresh and fruity complement.
- Coconut Flakes: Sprinkle toasted coconut flakes on top for added texture and flavor.
- Caramel Sauce Drizzle: Drizzle warm caramel sauce over the cupcakes before serving for a decadent touch.
How to Perfect Pineapple Upside Down Cupcakes
Achieving the perfect Pineapple Upside Down Cupcakes requires attention to detail and some helpful tips. Follow these guidelines to ensure your cupcakes turn out beautifully every time.
- Use Fresh Ingredients: Always opt for the freshest pineapple and high-quality butter for the best flavor.
- Proper Measuring: Measure flour accurately by spooning it into the measuring cup, then leveling it off with a knife to avoid dense cupcakes.
- Room Temperature Eggs: Ensure your eggs are at room temperature; this helps them blend better with other ingredients.
- Don’t Overmix: Gently fold the dry ingredients into the wet ingredients to prevent tough cupcakes.
- Check Doneness Carefully: Use a toothpick inserted into the center; if it comes out clean, your cupcakes are ready!
Best Side Dishes for Pineapple Upside Down Cupcakes
Pineapple Upside Down Cupcakes can be paired with various side dishes to create a well-rounded dessert experience. Here are some delicious options that complement their tropical flavors.
- Tropical Fruit Salad: A mix of diced mango, kiwi, and berries adds freshness and color.
- Coconut Rice Pudding: Creamy rice pudding infused with coconut milk enhances the tropical vibe.
- Mango Sorbet: Light and refreshing, this sorbet is perfect alongside warm cupcakes.
- Honeydew Melon Slices: Sweet melon slices add hydration and balance out the sweetness of the cupcakes.
- Yogurt Parfait: Layer yogurt with granola and fresh fruit for a satisfying contrast.
- Pineapple Salsa: A zesty salsa made with fresh pineapple, red onion, and cilantro brings an exciting twist.
Common Mistakes to Avoid
When making Pineapple Upside Down Cupcakes, it’s easy to overlook a few key details that can affect the outcome. Here are some common mistakes to watch out for:
- Incorrect oven temperature: Always preheat your oven to 350°F (175°C) to ensure even baking. An unheated oven can result in uneven cooking.
- Not using enough butter: The butter adds moisture and flavor. Ensure you measure the melted butter accurately for optimal taste and texture.
- Overmixing the batter: Mixing too much can lead to tough cupcakes. Mix until just combined for a fluffy texture.
- Skipping the cooling step: Allowing cupcakes to cool before inverting is crucial. This prevents sticking and ensures the pineapple topping stays intact.
- Using old ingredients: Check the freshness of your baking powder and flour. Expired ingredients can affect rise and flavor.

Storage & Reheating Instructions
Refrigerator Storage
- Store cupcakes in an airtight container.
- They will last for up to 5 days in the refrigerator.
Freezing Pineapple Upside Down Cupcakes
- Wrap each cupcake individually in plastic wrap.
- Place them in a freezer-safe container; they can be frozen for up to 3 months.
Reheating Pineapple Upside Down Cupcakes
- Oven: Preheat to 350°F (175°C) and heat for about 10 minutes.
- Microwave: Heat one cupcake at a time for about 15-20 seconds.
- Stovetop: Place in a skillet over low heat for about 5 minutes, covered, until warmed through.
Frequently Asked Questions
What are Pineapple Upside Down Cupcakes?
Pineapple Upside Down Cupcakes are individual-sized desserts featuring a moist cake topped with caramelized pineapple slices and cherries, offering a delightful tropical flavor.
How do I make my cupcakes moist?
To keep your cupcakes moist, use fresh ingredients, avoid overmixing, and ensure you don’t skip the butter in your recipe.
Can I use fresh pineapple instead of canned?
Yes! Fresh pineapple can be used, but make sure it is ripe and sweet for the best flavor in your Pineapple Upside Down Cupcakes.
How long do these cupcakes last?
These cupcakes can be stored in the refrigerator for up to 5 days or frozen for up to 3 months if wrapped properly.
Final Thoughts
Pineapple Upside Down Cupcakes are not only delicious but also versatile. You can customize them with different fruits or flavors based on your preference. Give this fun recipe a try and enjoy a taste of sunshine anytime!
Pineapple Upside Down Cupcakes
Indulge in the delightful experience of Pineapple Upside Down Cupcakes, a charming twist on the classic dessert that brings tropical flavors to your table. These individual cupcakes feature a moist vanilla base topped with caramelized pineapple and vibrant cherries, making them perfect for celebrations or a sweet everyday treat. Their playful presentation and refreshing taste will surely impress your guests at any gathering. With straightforward preparation steps, these cupcakes are suitable for bakers of all levels, ensuring a deliciously satisfying result every time.
- Prep Time: 15 minutes
- Cook Time: 17 minutes
- Total Time: 32 minutes
- Yield: Makes approximately 21 cupcakes 1x
- Category: Dessert
- Method: Baking
- Cuisine: Tropical
Ingredients
- ½ cup melted butter
- ½ cup packed brown sugar
- 1 can (20 ounces) pineapple slices or chunks with juice
- 21 maraschino cherries
- 2 cups all-purpose flour
- 2 teaspoons baking powder
- ½ teaspoon salt
- ½ teaspoon baking soda
- ¼ cup canola oil
- ¾ cup granulated sugar
- 2 large eggs
Instructions
- Preheat the oven to 350°F (175°C) and prepare a muffin tin with nonstick spray or liners.
- For the topping, cut pineapple into small pieces. In each muffin cup, add a teaspoon of melted butter and brown sugar, then arrange pineapple pieces and place a cherry in the center.
- In one bowl, whisk together flour, baking powder, salt, and baking soda. In another bowl, mix canola oil and granulated sugar until smooth; add eggs and combine.
- Fold dry ingredients into wet ingredients gently, then stir in reserved pineapple juice until smooth.
- Spoon batter into muffin cups and bake for 15–17 minutes until golden brown and a toothpick comes out clean.
- Let cool for 30 minutes before inverting onto a cooling rack.
Nutrition
- Serving Size: 1 cupcake (50g)
- Calories: 180
- Sugar: 15g
- Sodium: 160mg
- Fat: 7g
- Saturated Fat: 3g
- Unsaturated Fat: 4g
- Trans Fat: 0g
- Carbohydrates: 26g
- Fiber: <1g
- Protein: 2g
- Cholesterol: 35mg