Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, transforming the traditional flavors into fun, bite-sized servings. Perfect for birthday parties, picnics, or any gathering, these cupcakes promise to bring joy to your table. With their moist texture and sweet pineapple topping, they are sure to be a hit with both kids and adults alike.
Why You’ll Love This Recipe
- Easy to Make – This recipe simplifies the classic pineapple upside-down cake into individual cupcakes that are quick and simple to prepare.
- Delicious Flavor – The combination of sweet pineapple and brown sugar creates a mouthwatering taste that will have everyone asking for seconds.
- Versatile for Occasions – These cupcakes are ideal for celebrations, potlucks, or just a fun family treat. They can fit any occasion!
- Fun Presentation – Serving cupcakes instead of a whole cake makes for an attractive presentation that’s perfect for sharing.
- Customizable Toppings – Add powdered sugar, whipped cream, or extra cherries to make them even more special.
Tools and Preparation
Before you start baking your Pineapple Upside Down Cupcakes, make sure you have the right tools ready. Using the right kitchen tools can make your baking experience smoother and more enjoyable.
Essential Kitchen Tools
- Cupcake pan
- Mixing bowls
- Electric mixer
- Measuring cups and spoons
- Spatula
Why These Tools Matter
- Cupcake pan – Essential for creating perfectly shaped cupcakes that hold their form while baking.
- Electric mixer – Saves time and effort in mixing the batter evenly, ensuring a fluffy texture.
- Measuring cups and spoons – Accurate measurements are key to achieving consistent flavor and texture in your cupcakes.
Ingredients
Pineapple upside down cupcake bring the traditional taste you know and love into fun bite size 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 your cupcake pan by spraying it with non-stick cooking spray.
Step 2: Prepare the Filling
- 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 and gently press it into the mixture.
- Top each well with a tablespoon of crushed pineapple and gently compact it using the back of a spoon.
Step 3: Mix the Batter
In a large bowl:
1. Combine the cake mix, pineapple juice, canola oil, and eggs.
2. Beat with an electric mixer on low speed for about 2 minutes until well combined.
Step 4: Fill the Cupcake Wells
Scoop or pour the batter over the prepared fillings in each muffin cup. Fill them to the top but avoid overfilling.
Step 5: Bake
Bake in the preheated oven for approximately 20 minutes. Check if done by inserting a toothpick into the center; it should come out clean. Remove from oven and let cool for about 10 minutes.
Step 6: Invert and Serve
After cooling for 10 minutes, gently invert the pan onto a cooling rack or sheet pan to release your cupcakes. Enjoy your delicious Pineapple Upside Down Cupcakes fresh!
How to Serve Pineapple Upside Down Cupcakes
Serving your Pineapple Upside Down Cupcakes is just as important as making them. These delightful treats can be enjoyed in various ways that enhance their tropical flavor and festive presentation.
Individual Treats
- Serve with a cherry on top: Adding a fresh maraschino cherry elevates the look and adds an extra burst of sweetness.
- Drizzle with whipped cream: A light drizzle of whipped cream can add a creamy texture that balances the flavors beautifully.
- Garnish with pineapple slices: Place a small slice of fresh pineapple on the side for added flavor and decoration.
Party Platter
- Group serving: Arrange cupcakes on a decorative platter, creating an eye-catching centerpiece for any gathering.
- Themed decorations: Use tropical-themed plates and napkins to complement the island vibes of these cupcakes.
Pairing Options
- Accompany with fruit salad: A refreshing fruit salad provides a nice contrast to the sweet cupcakes, making them even more enjoyable.
- Serve with iced tea or lemonade: The citrusy flavors of lemonade or the refreshing taste of iced tea pair wonderfully with these cupcakes.
How to Perfect Pineapple Upside Down Cupcakes
Perfecting your Pineapple Upside Down Cupcakes ensures they come out moist and flavorful every time. Here are some tips to help you achieve cupcake perfection.
- Use fresh ingredients: Always opt for fresh eggs and quality butter for better flavor and texture.
- Don’t overmix batter: Gently combine ingredients to keep the cupcakes light and fluffy; overmixing can lead to dense cupcakes.
- Check oven temperature: Ensure your oven is calibrated correctly; an accurate temperature prevents undercooking or burning.
- Cool before inverting: Allowing the cupcakes to cool slightly before inverting helps maintain their shape and prevents sticking.
- Experiment with toppings: Feel free to get creative with toppings like shredded coconut or toasted nuts for added texture.

Best Side Dishes for Pineapple Upside Down Cupcakes
Pairing side dishes with your Pineapple Upside Down Cupcakes can enhance your dessert experience. Here are some delicious options.
- Fresh Fruit Salad: A mix of seasonal fruits brightens the table and complements the sweetness of the cupcakes.
- Coconut Rice: This subtly sweet side dish offers a tropical twist that pairs well with the flavors of the cupcakes.
- Coleslaw: A tangy coleslaw brings a refreshing crunch that contrasts nicely with the soft texture of the cupcakes.
- Grilled Chicken Skewers: Lightly seasoned chicken skewers provide protein, making it a balanced meal when served alongside dessert.
- Vegetable Spring Rolls: Crisp spring rolls filled with veggies offer a light, crunchy option that pairs well with sweet treats.
- Caribbean Black Beans: Flavorful black beans add depth to your meal, enhancing the overall tropical theme.
Common Mistakes to Avoid
When making Pineapple Upside Down Cupcakes, it’s easy to overlook a few key steps. Here are some common mistakes to keep in mind.
- Ignoring the Measurements: Always measure your ingredients accurately. Too much or too little of any ingredient can affect the texture and taste.
- Not Draining the Pineapple: Ensure you drain the crushed pineapple well. Excess liquid can lead to soggy cupcakes.
- Overfilling the Cupcake Wells: Avoid overfilling the cupcake wells. Filling them to the top may cause overflow during baking, resulting in messy cupcakes.
- Skipping the Cooling Step: Allow cupcakes to cool for about 10 minutes before inverting. Skipping this step can cause them to break apart.
- Using Cold Ingredients: Make sure your eggs and other ingredients are at room temperature. Cold ingredients can lead to uneven mixing and texture.
Storage and Reheating
Refrigerator Storage
- Store leftover cupcakes in an airtight container.
- They can last up to 3 days in the fridge.
- Place parchment paper between layers for better preservation.
Freezing Pineapple Upside Down Cupcakes
- Wrap each cupcake individually in plastic wrap.
- Place wrapped cupcakes in a freezer-safe bag or container.
- They can be frozen for up to 2 months.
Reheating Pineapple Upside Down Cupcakes
- Oven: Preheat to 350°F (175°C) and heat for about 10 minutes until warm.
- Microwave: Heat on medium power for 20-30 seconds for a quick warm-up.
- Stovetop: Use a skillet on low heat; cover with a lid for a few minutes until heated through.

Frequently Asked Questions
What makes Pineapple Upside Down Cupcakes special?
Pineapple Upside Down Cupcakes are unique because they transform a classic dessert into individual servings, offering both flavor and fun presentation.
Can I use fresh pineapple instead of canned?
Yes! Fresh pineapple can be used, but ensure it is well-drained if you choose to cut it yourself.
How do I customize my Pineapple Upside Down Cupcakes?
You can add nuts like pecans or walnuts, or even coconut flakes for added texture and flavor!
How long do Pineapple Upside Down Cupcakes last?
When stored properly, these cupcakes last up to 3 days in the refrigerator or up to 2 months if frozen.
Conclusion
Pineapple Upside Down Cupcakes are deliciously sweet and visually appealing, making them perfect for any occasion. Their versatility allows you to customize toppings and flavors, so don’t hesitate to get creative! Try this delightful recipe today!
Pineapple Upside Down Cupcakes
- Total Time: 35 minutes
- Yield: Approximately 24 servings 1x
Description
Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, offering a fun and portable way to enjoy the beloved flavors of pineapple and cherry. With their moist texture and sweet topping, these individual treats are perfect for any celebration—from birthday parties to casual family gatherings. Each cupcake features a luscious layer of crushed pineapple and a cherry, making them visually appealing and irresistibly delicious. Easy to make and highly customizable, these cupcakes can be adorned with whipped cream or fresh fruit for an extra special touch.
Ingredients
- 1/2 cup melted butter (salted or unsalted)
- 1 1/2 cups light brown sugar
- 24 maraschino cherries
- 20 ounces crushed pineapple (drained)
- 15.25 ounces 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 your oven to 375°F (190°C) and prepare a cupcake pan with non-stick cooking spray.
- In each well of the pan, add about 1 teaspoon of melted butter, followed by 1 tablespoon of brown sugar. Press one maraschino cherry into the mixture, then top with a tablespoon of drained crushed pineapple.
- In a large mixing bowl, combine the cake mix, pineapple juice, canola oil, and eggs. Mix using an electric mixer on low for about 2 minutes until smooth.
- Fill each cupcake well with batter until just full.
- Bake for approximately 20 minutes or until a toothpick inserted comes out clean. Allow cooling for about 10 minutes before inverting onto a cooling rack.
- Prep Time: 15 minutes
- Cook Time: 20 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cupcake (70g)
- Calories: 210
- Sugar: 18g
- Sodium: 150mg
- Fat: 8g
- Saturated Fat: 4g
- Unsaturated Fat: 4g
- Trans Fat: 0g
- Carbohydrates: 34g
- Fiber: <1g
- Protein: 2g
- Cholesterol: 60mg



