Pineapple Upside Down Cupcakes bring the traditional taste you know and love into fun bite-sized servings. These delightful treats are perfect for any occasion, whether it’s a birthday party, a family gathering, or just a cozy night in. Their unique presentation and tropical flavor make them a standout dessert that everyone will adore.
Why You’ll Love This Recipe
- Easy to Make: With simple ingredients and straightforward steps, you’ll have these cupcakes ready in no time.
- Fun Presentation: The upside-down style makes for an eye-catching treat that’s sure to impress your guests.
- Versatile Flavor: The sweet pineapple paired with cherries creates a deliciously tropical flavor that appeals to all ages.
- Perfect for Any Occasion: Whether it’s a celebration or a casual get-together, these cupcakes fit right in.
- Customizable Toppings: Add powdered sugar, whipped cream, or extra cherries to elevate your dessert experience.
Tools and Preparation
Before diving into this mouthwatering recipe, gather your kitchen tools. Having everything ready makes the baking process smoother and more enjoyable.
Essential Kitchen Tools
- Cupcake pan
- Non-stick cooking spray
- Mixing bowl
- Electric mixer
- Measuring cups and spoons
Why These Tools Matter
- Cupcake pan: Essential for baking evenly shaped cupcakes that have the perfect texture.
- Electric mixer: Makes mixing ingredients quick and easy, ensuring a smooth batter without lumps.
- Measuring cups and spoons: Ensures accurate ingredient measurements for consistent results every time.
Ingredients
Pineapple upside down cupcake bring the traditional taste you know and love into fun bite-sized servings.
Ingredients:
– 1/2 cup melted butter (salted or unsalted)
– 1 1/2 cups light brown sugar
– 24 maraschino cherries
– 20 ounces can crushed pineapple (drained)
– 15.25 ounce box pineapple cake mix (any box between 15-18 ounces will work)
– 1 1/3 cups pineapple juice
– 1/3 cups canola oil
– 3 eggs
– optional toppings such as powdered sugar, additional cherries, and/or whipped cream, as desired

How to Make Pineapple Upside Down Cupcakes
Step 1: Preheat the Oven
Preheat your oven to 375 degrees F. Prepare the cupcake pan by spraying it with non-stick cooking spray to ensure easy removal of the cupcakes later.
Step 2: Prepare the Cupcake Wells
- Spoon approximately 1 teaspoon of melted butter into each well of the cupcake pan.
- Add 1 tablespoon of brown sugar to each well.
- Place one maraschino cherry on top of the brown sugar in each well. Gently press it into the mixture.
- On top of that, add a tablespoon of crushed pineapple to each well and gently press it down with the back of a spoon to compact it.
Step 3: Mix the Batter
In a large mixing bowl, combine:
1. Cake mix
2. Pineapple juice
3. Canola oil
4. Eggs
Beat with an electric mixer on low speed for about 2 minutes until well blended.
Step 4: Fill the Cupcake Wells
Scoop or pour batter into each muffin cup on top of the prepared fillings. Fill each well to the top but avoid overfilling to allow room for rising.
Step 5: Bake the Cupcakes
Bake in your preheated oven for approximately 20 minutes. Check doneness by inserting a toothpick into the center; it should come out clean when done. Remove from oven and let cool for about 10 minutes.
Step 6: Invert and Cool
After cooling for 10 minutes, gently invert the pan onto a cooling rack or sheet pan. This will release your beautifully topped cupcakes without mess! Enjoy your Pineapple Upside Down Cupcakes either warm or at room temperature.
How to Serve Pineapple Upside Down Cupcakes
Pineapple upside down cupcakes are delightful treats that can be served in various ways, making them perfect for any occasion. Whether you are hosting a party or enjoying a quiet evening at home, here are some creative serving suggestions.
Individual Treats
- Serve each cupcake on a small plate for an elegant touch, perfect for parties or special gatherings.
With Whipped Cream
- Top each cupcake with a dollop of whipped cream. This adds a creamy texture that complements the sweetness of the pineapple.
Accompanied by Fresh Fruit
- Pair cupcakes with fresh fruit like strawberries or kiwi for a colorful and refreshing contrast on your dessert table.
Dusting of Powdered Sugar
- Lightly sprinkle powdered sugar on top of the cupcakes just before serving for an extra sweet finish.
Served Warm
- Warm the cupcakes slightly in the microwave before serving to enhance their flavors and give them a comforting touch.
With Ice Cream
- Serve alongside a scoop of vanilla ice cream for an indulgent dessert experience that balances the fruity flavors.
How to Perfect Pineapple Upside Down Cupcakes
To make sure your pineapple upside down cupcakes turn out perfectly every time, consider these helpful tips.
- Use Fresh Ingredients: Always use fresh eggs and high-quality ingredients for the best flavor and texture.
- Don’t Overmix the Batter: Mixing too much can make your cupcakes dense. Stir until just combined for fluffy results.
- Check Oven Temperature: Make sure your oven is preheated correctly. An oven thermometer can help ensure accurate baking temperatures.
- Cool Before Inverting: Allow the cupcakes to cool slightly before inverting them to avoid breaking their delicate tops.
- Store Properly: Keep any leftovers in an airtight container at room temperature to maintain their moisture and flavor.
- Experiment with Toppings: Feel free to get creative with toppings like nuts or coconut flakes for added texture and flavor.

Best Side Dishes for Pineapple Upside Down Cupcakes
When serving pineapple upside down cupcakes, pairing them with side dishes can create a well-rounded dessert spread. Here are some great options:
- Fruit Salad: A mix of seasonal fruits provides freshness and balances the sweetness of the cupcakes.
- Yogurt Parfait: Layer yogurt with granola and fruit for a creamy, crunchy complement.
- Cheese Platter: Include mild cheeses; they provide a savory contrast that enhances the cupcake’s flavors.
- Chocolate Dipped Strawberries: These add an elegant touch and contrasting flavors that guests will love.
- Nut Mix: A bowl of mixed nuts offers crunchiness and pairs nicely with sweet desserts.
- Minted Watermelon Slices: Refreshing watermelon slices drizzled with mint dressing offer a light side option.
- Savory Crackers: Serve with cheese spreads or dips for guests who enjoy salty snacks alongside sweets.
- Coconut Macaroons: These chewy treats echo tropical flavors while providing variety on your dessert table.
Common Mistakes to Avoid
When making Pineapple Upside Down Cupcakes, it’s easy to encounter a few common pitfalls. Here are some mistakes to watch out for:
- Ignoring the cooling time: Allowing cupcakes to cool for at least 10 minutes before inverting them helps prevent sticking and ensures they come out intact.
- Overfilling the cupcake wells: Filling the wells too much can cause the batter to overflow while baking. Aim to fill them just below the rim for perfect results.
- Not draining the pineapple properly: Excess moisture from drained pineapple can make your cupcakes soggy. Ensure you drain well before adding it to the mixture.
- Using cold ingredients: Make sure your eggs and other ingredients are at room temperature. This helps create a fluffier texture in your cupcakes.
- Skipping the non-stick spray: Even when using butter, spraying with non-stick spray can help ensure easy release from the pan.
Storage and Reheating
Refrigerator Storage
- Duration: Pineapple Upside Down Cupcakes can be stored in the refrigerator for up to 4 days.
- Containers: Use an airtight container to maintain freshness and prevent drying out.
Freezing Pineapple Upside Down Cupcakes
- Duration: These cupcakes can be frozen for up to 3 months.
- Containers: Place them in a freezer-safe container or wrap each cupcake tightly in plastic wrap followed by aluminum foil.
Reheating Pineapple Upside Down Cupcakes
- Oven: Preheat your oven to 350°F (175°C). Place cupcakes on a baking sheet and heat for about 10-15 minutes until warm.
- Microwave: Heat individual cupcakes on a microwave-safe plate for 10-15 seconds until warmed through. Be careful not to overheat as this can dry them out.
- Stovetop: Use a skillet with a lid over low heat. Place cupcakes in the skillet, cover, and warm for about 5-7 minutes.

Frequently Asked Questions
What are Pineapple Upside Down Cupcakes?
Pineapple Upside Down Cupcakes are deliciously moist cakes topped with caramelized pineapple and cherries, served in individual portions, making them perfect for any occasion.
Can I customize my Pineapple Upside Down Cupcakes?
Absolutely! You can add nuts, different fruits, or even spices like cinnamon to enhance flavor according to your taste preferences.
How do I know when my Pineapple Upside Down Cupcakes are done?
Insert a toothpick into the center of a cupcake; if it comes out clean, they are done baking.
Can I use fresh pineapple instead of canned?
Yes, using fresh pineapple is great! Just ensure it’s finely chopped and drained well before adding it to your cupcake mixture.
Conclusion
These Pineapple Upside Down Cupcakes are not only visually appealing but also bursting with flavor. Their versatility allows you to customize toppings or mix-ins according to your preferences. Try making these delightful treats today—perfect for gatherings or as a sweet indulgence!
Pineapple Upside Down Cupcakes
- Total Time: 35 minutes
- Yield: Makes approximately 12 servings 1x
Description
Indulge in the delightful world of Pineapple Upside Down Cupcakes, where classic flavors meet modern convenience! These charming cupcakes combine sweet pineapple and vibrant cherries in a bite-sized treat that’s perfect for any occasion.
Ingredients
- 1/2 cup melted butter (salted or unsalted)
- 1 1/2 cups light brown sugar
- 24 maraschino cherries
- 20 ounces can crushed pineapple (drained)
- 15.25 ounce box pineapple cake mix
- 1 1/3 cups pineapple juice
- 1/3 cup canola oil
- 3 eggs
- Optional toppings: powdered sugar, additional cherries, whipped cream
Instructions
- Preheat oven to 375°F and prepare cupcake pan with non-stick spray.
- Spoon melted butter and brown sugar into each cupcake well; add maraschino cherry and crushed pineapple.
- In a mixing bowl, combine cake mix, pineapple juice, canola oil, and eggs. Mix on low speed until blended.
- Fill each cupcake well with batter.
- Bake for approximately 20 minutes or until a toothpick comes out clean.
- Cool slightly before inverting onto a rack.
- Prep Time: 15 minutes
- Cook Time: 20 minutes
- Category: Dessert
- Method: Baking
- Cuisine: Tropical
Nutrition
- Serving Size: 1 cupcake (65g)
- Calories: 190
- Sugar: 24g
- Sodium: 180mg
- Fat: 8g
- Saturated Fat: 4g
- Unsaturated Fat: 4g
- Trans Fat: 0g
- Carbohydrates: 29g
- Fiber: <1g
- Protein: 2g
- Cholesterol: 40mg



