Pineapple Upside Down Cupcakes
Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, perfect for parties, picnics, or any occasion that calls for a sweet treat. These mini cupcakes pack a punch of tropical flavor with crushed pineapple and a brown sugar caramel topping, all crowned with a cherry. Their individual servings make them easy to enjoy and share, ensuring everyone can indulge in this fun and flavorful dessert.

Why You’ll Love This Recipe
- Quick and Easy: This recipe makes use of a cake mix, allowing you to whip up these cupcakes in no time.
- Tropical Flavor: The combination of crushed pineapple and caramel creates a deliciously moist cupcake that bursts with flavor.
- Perfect for Any Occasion: Whether it’s a birthday party or just a sweet treat at home, these cupcakes are always a hit.
- Individual Servings: Mini cupcakes make portion control easy while still delivering the delicious taste of pineapple upside down cake.
- Fun Presentation: The vibrant colors and toppings make these cupcakes visually appealing, perfect for impressing guests.
Tools and Preparation
Before diving into making your Pineapple Upside Down Cupcakes, gather the necessary tools to ensure smooth preparation.
Essential Tools and Equipment
- Muffin tin
- Cooking spray
- Mixing bowl
- Whisk
- Parchment paper
- Toothpick
Importance of Each Tool
- Muffin tin: Essential for shaping your cupcakes and ensuring they bake evenly.
- Whisk: Helps combine ingredients smoothly for a fluffy batter.
- Parchment paper: Makes cleanup easy and prevents sticking when inverting the cupcakes.
Ingredients
Pineapple Upside Down Cupcakes stuffed with crushed pineapple, brown sugar caramel, and a cherry on top! Easy cupcakes made from a cake mix with mega pineapple flavor.
For the Topping
- Cooking spray
- 1/2 cup butter (melted)
- 1 1/2 cups brown sugar
- 24 maraschino cherries
- 20 oz can crushed pineapple (reserve juice)
For the Cupcake Batter
- 15.25 oz package yellow cake mix
- Vegetable oil and eggs per cake mix instructions
- 1 1/3 cups pineapple juice
Optional Finishing Touch
- Confectioners’ sugar for dusting (optional)
How to Make Pineapple Upside Down Cupcakes
Step 1: Preheat the Oven
Preheat your oven to 350°F. This ensures that your Pineapple Upside Down Cupcakes bake evenly.
Step 2: Prepare the Muffin Cups
- Spray 24 muffin cups with cooking spray to prevent sticking.
- Line a surface with parchment paper where you will invert the cupcakes later.
Step 3: Add Butter and Brown Sugar
In each muffin cup:
1. Add 1 teaspoon of melted butter.
2. Sprinkle 1 tablespoon of brown sugar over the butter.
Step 4: Place Cherries and Pineapple
- Place one maraschino cherry in the center of each cup.
- Top each cherry with a heaping tablespoon of crushed pineapple.
Step 5: Make the Cake Batter
Prepare the cake batter according to package instructions, but replace water with reserved pineapple juice for extra flavor.
Step 6: Fill Muffin Cups
Pour the prepared batter into each muffin cup, filling almost to the top.
Step 7: Bake
Bake in the preheated oven for 18-22 minutes. Check if they are done by inserting a toothpick; it should come out clean.
Step 8: Cool and Invert
Allow the cupcakes to cool in the pan for about 5 minutes. Then invert them onto your prepared parchment paper to release them.
Step 9: Dust with Sugar (Optional)
For an extra touch of sweetness, dust with confectioners’ sugar before serving your Pineapple Upside Down Cupcakes.
How to Serve Pineapple Upside Down Cupcakes
Pineapple Upside Down Cupcakes are a delightful treat that can be enjoyed in various ways. Whether you’re hosting a party or just satisfying your sweet tooth, these cupcakes can be served in creative and fun manners.
Individual Dessert Plates
- Arrange each cupcake on a small plate, garnished with fresh mint leaves for a pop of color.
Ice Cream Pairing
- Serve warm cupcakes alongside a scoop of vanilla ice cream to create a delicious contrast of temperatures.
Festive Platter
- Create a dessert platter with an assortment of cupcakes, sliced fruits, and whipped cream for a colorful display.
Mini Dessert Shooters
- Layer pieces of cupcake with whipped cream and crushed pineapple in small dessert cups for an elegant presentation.
Party Favors
- Package individual cupcakes in clear bags tied with ribbon as sweet take-home treats for guests.
Coffee or Tea Companion
- Pair these cupcakes with a cup of coffee or tea for an enjoyable afternoon snack.

How to Perfect Pineapple Upside Down Cupcakes
To ensure your Pineapple Upside Down Cupcakes turn out perfectly every time, follow these simple tips.
- Use fresh ingredients: Always opt for fresh butter and eggs for the best flavor and texture.
- Measure accurately: Ensure you measure your ingredients precisely to maintain the right balance in the batter.
- Don’t overmix: Mix the batter just until combined; overmixing can lead to dense cupcakes.
- Check oven temperature: Use an oven thermometer to confirm your oven is at the correct temperature before baking.
- Cool before serving: Allow the cupcakes to cool slightly before inverting them onto parchment paper for easier handling.
- Customize toppings: Feel free to add other toppings like toasted coconut or chopped nuts for extra flavor and texture.
Best Side Dishes for Pineapple Upside Down Cupcakes
Serving side dishes alongside Pineapple Upside Down Cupcakes can enhance your dessert experience. Here are some delightful options to consider:
- Coconut Macaroons: Chewy and sweet, these pair well with the tropical flavors of the cupcakes.
- Fruit Salad: A refreshing mix of seasonal fruits complements the sweetness of the cupcakes beautifully.
- Chocolate Mousse: Rich and creamy chocolate mousse provides a decadent contrast to fruity flavors.
- Cream Cheese Frosting Dip: Serve this rich dip with graham crackers or fruit slices for added indulgence.
- Pineapple Sorbet: A light, fruity sorbet enhances the pineapple flavor while keeping it refreshing.
- Cheesecake Bites: Mini cheesecake bites offer a creamy texture that balances nicely with the cake’s softness.
- Whipped Cream Topping: Lightly sweetened whipped cream adds a fluffy touch to each bite.
- Almond Biscotti: These crunchy cookies provide a satisfying crunch alongside your moist cupcakes.
Common Mistakes to Avoid
Avoiding common mistakes can make your Pineapple Upside Down Cupcakes even better. Here are some pitfalls to watch out for:
- Skipping the cooking spray: Not using cooking spray may lead to cupcakes sticking to the muffin cups. Always spray before adding ingredients.
- Overfilling the cups: Filling the muffin cups too high can cause overflow while baking. Fill them just under the rim for best results.
- Using cold ingredients: Cold butter or eggs can affect the batter’s consistency. Ensure all ingredients are at room temperature before mixing.
- Ignoring baking time: Overbaking can dry out your cupcakes. Keep an eye on them and use a toothpick to check for doneness around 18 minutes.
- Not inverting carefully: Inverting too quickly can cause toppings to fall off. Let them cool slightly before inverting onto parchment paper to maintain their structure.
Storage & Reheating Instructions
Refrigerator Storage
- Duration: Store in the refrigerator for up to 5 days.
- Container: Place in an airtight container to keep them fresh.
Freezing Pineapple Upside Down Cupcakes
- Duration: Freeze for up to 2 months.
- Container: Use a freezer-safe container or wrap each cupcake individually in plastic wrap before placing in a zip-top bag.
Reheating Pineapple Upside Down Cupcakes
- Oven: Preheat to 350°F and heat for about 10-15 minutes until warm.
- Microwave: Heat one cupcake at a time on medium power for about 30 seconds.
- Stovetop: Use a skillet over low heat, covering it with a lid. Heat for about 5 minutes until warmed through.
Frequently Asked Questions
Here are some common questions about making Pineapple Upside Down Cupcakes that might help you out:
Can I make these cupcakes ahead of time?
Yes, you can prepare the cupcakes a day before serving. Just store them properly in the refrigerator and bring them back to room temperature before serving.
How do I know when my cupcakes are done?
Insert a toothpick into the center of a cupcake; if it comes out clean, they are done baking.
What can I substitute for crushed pineapple in Pineapple Upside Down Cupcakes?
You can use diced fresh pineapple or canned pineapple chunks, but ensure they are well-drained if using chunks.
Can I use other fruits instead of pineapple?
Absolutely! You can experiment with other fruits like peaches or cherries by following the same method.
What is the best way to decorate Pineapple Upside Down Cupcakes?
You can dust them with confectioners’ sugar or add whipped cream on top for extra flair!
Final Thoughts
These Pineapple Upside Down Cupcakes are not only delicious but also versatile! You can customize them by adding different fruits or toppings according to your taste. They make a perfect dessert for any occasion, so give this recipe a try today!

Pineapple Upside Down Cupcakes
- Total Time: 35 minutes
- Yield: Makes 24 cupcakes 1x
Description
Pineapple Upside Down Cupcakes are a delightful and tropical twist on the classic dessert. These mini treats feature a moist yellow cake infused with crushed pineapple, topped with a luscious brown sugar caramel and a cherry, making them perfect for parties or casual gatherings. Individual servings make them easy to serve and share, ensuring everyone can relish this fun, flavorful dessert.
Ingredients
- 1 package yellow cake mix (15.25 oz)
- 1/2 cup butter (melted)
- 1 1/2 cups brown sugar
- 20 oz can crushed pineapple (reserve juice)
- 24 maraschino cherries
- Vegetable oil and eggs as per cake mix instructions
- Optional: Confectioners' sugar for dusting
Instructions
- Preheat your oven to 350°F.
- Spray 24 muffin cups with cooking spray and line with parchment paper.
- In each cup, add 1 teaspoon of melted butter followed by 1 tablespoon of brown sugar.
- Place one maraschino cherry in the center of each cup and top with crushed pineapple.
- Prepare the cake batter according to package directions, replacing water with reserved pineapple juice.
- Fill muffin cups almost to the top with batter.
- Bake for 18-22 minutes or until a toothpick comes out clean.
- Allow cupcakes to cool for about 5 minutes before inverting onto parchment paper.
- Dust with confectioners' sugar if desired before serving.
- Prep Time: 15 minutes
- Cook Time: 20 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cupcake (50g)
- Calories: 180
- Sugar: 12g
- Sodium: 150mg
- Fat: 7g
- Saturated Fat: 4g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 27g
- Fiber: <1g
- Protein: 2g
- Cholesterol: 30mg