Pineapple Upside Down Cupcakes
Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert. These mini cakes are perfect for any occasion, whether it’s a birthday party, potluck, or just a sweet treat for your family. With their moist, pineapple-infused cake and delicious caramelized topping, these cupcakes bring joy to every bite. Plus, they are easy to make using a simple cake mix!

Why You’ll Love This Recipe
- Quick and Easy: This recipe uses a cake mix, making preparation fast and hassle-free.
- Delicious Flavors: The combination of crushed pineapple and brown sugar creates a flavor explosion that will impress everyone.
- Perfect for Sharing: With 20 individual servings, these cupcakes are ideal for gatherings or events.
- Fun Presentation: Each cupcake comes with its own cherry on top, making them look as good as they taste.
- Versatile Treat: Enjoy them at parties, picnics, or even as an everyday dessert.
Tools and Preparation
Before you start baking your Pineapple Upside Down Cupcakes, gather the necessary tools. Having everything ready will make the process smooth and enjoyable.
Essential Tools and Equipment
- Muffin pan
- Parchment paper
- Mixing bowl
- Measuring cups and spoons
- Whisk or mixer
Importance of Each Tool
- Muffin pan: Essential for shaping the cupcakes perfectly.
- Parchment paper: Helps in easy release of cupcakes after baking.
- Mixing bowl: Necessary for combining ingredients without spilling.
- Measuring cups and spoons: Ensure accurate ingredient measurements for best results.
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 Cake Batter
- 15.25 oz package yellow cake mix
- Vegetable oil and eggs per cake mix instructions
- 1 1/3 cups pineapple juice
Optional Decoration
- Confectioners’ sugar for dusting
How to Make Pineapple Upside Down Cupcakes
Step 1: Preheat the Oven
Preheat your oven to 350°F (175°C). This ensures that your cupcakes bake evenly.
Step 2: Prepare Muffin Cups
Spray 24 muffin cups with cooking spray to prevent sticking. Line a surface with parchment paper to cool the cupcakes later.
Step 3: Add Butter and Sugar
Add 1 tsp of melted butter to each muffin cup. Follow this by adding 1 tbsp of brown sugar to each cup.
Step 4: Add Cherries and Pineapple
Place one cherry in the center of each cup. Top each cherry with a heaping tablespoon of crushed pineapple.
Step 5: Make Cake Batter
Prepare the cake batter according to package instructions. Replace water with the reserved pineapple juice to enhance flavor.
Step 6: Fill Muffin Cups
Pour the batter into each prepared muffin cup, filling almost to the top.
Step 7: Bake the Cupcakes
Bake in the preheated oven for about 18-22 minutes. Check doneness by inserting a toothpick; it should come out clean.
Step 8: Cool and Release
Allow cupcakes to cool in the pan for about 5 minutes. Then invert them onto parchment paper to release them gently.
Step 9: Optional Dusting
For an extra touch of sweetness, dust with confectioners’ sugar before serving if desired.
Enjoy your delicious Pineapple Upside Down Cupcakes! They are sure to be a hit wherever you serve them!
How to Serve Pineapple Upside Down Cupcakes
Pineapple Upside Down Cupcakes are a delightful treat that can be enjoyed in various ways. Their charming presentation makes them perfect for gatherings, parties, or just a cozy night at home. Here are some serving suggestions to elevate your cupcake experience.
Individual Dessert Plates
- Serve each cupcake on its own dessert plate for an elegant touch.
- Add a dollop of whipped cream or a scoop of vanilla ice cream beside it for extra indulgence.
Tropical Fruit Salad
- Pair with a refreshing tropical fruit salad.
- Combine diced mango, kiwi, and strawberries for a colorful complement.
Coconut Flavored Icing
- Drizzle with coconut flavored icing for an enhanced tropical vibe.
- The creamy texture balances the sweetness of the cupcakes perfectly.
Coffee or Tea
- Enjoy these cupcakes with a warm cup of coffee or tea.
- The rich flavors of the cupcake pair well with both bold and light beverages.
Garnish with Mint Leaves
- Top each cupcake with fresh mint leaves for a pop of color.
- This adds freshness and enhances the visual appeal.

How to Perfect Pineapple Upside Down Cupcakes
To ensure your Pineapple Upside Down Cupcakes turn out perfectly every time, consider these helpful tips.
- Use Fresh Ingredients: Always opt for fresh eggs and quality butter. This will enhance the flavor and texture of your cupcakes.
- Don’t Overmix the Batter: Mix just until combined. Overmixing can lead to dense cupcakes instead of light and fluffy ones.
- Check Oven Temperature: Use an oven thermometer to ensure accurate baking temperatures. An incorrect temperature can affect baking time and results.
- Cool Before Serving: Allow cupcakes to cool slightly before inverting them. This helps maintain their shape and prevents breakage.
Best Side Dishes for Pineapple Upside Down Cupcakes
These Pineapple Upside Down Cupcakes are delicious on their own but can be complemented by several side dishes. Here’s a list of great pairings that will enhance your dessert experience.
- Vanilla Ice Cream: A classic pairing that adds creaminess to the sweet flavors of the cupcake.
- Coconut Sorbet: Offers a refreshing contrast with its light texture and tropical taste.
- Fruit Compote: A warm fruit compote can add moisture and flavor, enhancing each bite.
- Chocolate Sauce: Drizzle chocolate sauce over the top for those who love chocolatey desserts.
- Pineapple Salsa: A zesty pineapple salsa can bring out the fruity notes in the cupcakes.
- Cream Cheese Frosting: Spread a light layer of cream cheese frosting on top for added richness.
Common Mistakes to Avoid
When making Pineapple Upside Down Cupcakes, it’s easy to overlook a few key details that can impact the final result. Here are some common mistakes to watch out for:
- Using cold ingredients: Always use room temperature eggs and butter. Cold ingredients can lead to uneven baking.
- Not measuring the pineapple juice: Ensure you measure the pineapple juice accurately. Too much or too little can affect the batter consistency.
- Skipping the cooling step: Allow cupcakes to cool before inverting. This prevents them from breaking apart.
- Overfilling muffin cups: Fill cups only three-quarters full to allow room for rising without spilling over.
- Neglecting to grease muffin pans: Use cooking spray generously on muffin pans to ensure easy removal after baking.
Storage & Reheating Instructions
Refrigerator Storage
- item Store Pineapple Upside Down Cupcakes in an airtight container.
- item They will last up to 3 days in the refrigerator.
Freezing Pineapple Upside Down Cupcakes
- item Wrap each cupcake individually in plastic wrap.
- item Place wrapped cupcakes in a freezer-safe container or bag.
- item They can be frozen for up to 2 months.
Reheating Pineapple Upside Down Cupcakes
- Oven: Preheat your oven to 350°F and warm cupcakes for about 10 minutes.
- Microwave: Heat one cupcake at a time for about 15-20 seconds until warm.
- Stovetop: Use a skillet over low heat with a lid; warm for about 5 minutes.
Frequently Asked Questions
Here are some common questions about making Pineapple Upside Down Cupcakes.
How do I make Pineapple Upside Down Cupcakes from scratch?
You can substitute the cake mix with homemade yellow cake batter, using similar ingredients and methods outlined in this recipe.
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple can be used, but make sure to finely chop it and adjust the sweetness if needed.
What are some variations of Pineapple Upside Down Cupcakes?
Try adding coconut flakes or macadamia nuts for a tropical twist on these delicious cupcakes.
How should I store leftover Pineapple Upside Down Cupcakes?
Store them in an airtight container in the refrigerator for up to 3 days or freeze them for longer storage.
Final Thoughts
These Pineapple Upside Down Cupcakes are not only delicious but also versatile. You can easily customize them with different fruits or toppings. Whether you enjoy them as a treat or serve them at gatherings, they are sure to impress. Give this recipe a try and enjoy every bite!

Pineapple Upside Down Cupcakes
- Total Time: 37 minutes
- Yield: Approximately 24 cupcakes 1x
Description
Pineapple Upside Down Cupcakes are a delightful and fun twist on the classic dessert, perfect for any celebration or as an everyday treat. Imagine moist yellow cake infused with crushed pineapple, topped with a luscious caramel layer and a bright cherry. These mini cakes are not only visually appealing but also bursting with tropical flavors that will take your taste buds on a delicious journey. With an easy-to-follow recipe using cake mix, you can whip up these individual servings in no time, making them ideal for birthdays, potlucks, or simply to brighten your family’s day.
Ingredients
- 1 package yellow cake mix (15.25 oz)
- 1 1/2 cups brown sugar
- 1/2 cup butter (melted)
- 24 maraschino cherries
- 20 oz can crushed pineapple (reserve juice)
- Vegetable oil and eggs as per cake mix instructions
- 1 1/3 cups pineapple juice
Instructions
- Preheat your oven to 350°F (175°C) and prepare a muffin pan with cooking spray.
- In each muffin cup, add 1 tsp melted butter followed by 1 tbsp brown sugar.
- Place one cherry in the center of each cup and top with heaping tablespoons of crushed pineapple.
- Prepare the cake batter according to package instructions, replacing water with reserved pineapple juice.
- Pour the batter into each prepared muffin cup until nearly full.
- Bake for 18-22 minutes, checking doneness with a toothpick.
- Allow cupcakes to cool for about 5 minutes before inverting onto parchment paper.
- Optionally dust with confectioners' sugar before serving.
- Prep Time: 15 minutes
- Cook Time: 22 minutes
- Category: Dessert
- Method: Baking
- Cuisine: Tropical
Nutrition
- Serving Size: 1 cupcake (69g)
- Calories: 211
- Sugar: 17g
- Sodium: 173mg
- Fat: 8g
- Saturated Fat: 4g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 34g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 37mg