Pineapple Upside Down Cupcakes

Last updated on June 2, 2025

If you’re a fan of delightful desserts that combine sweet, fruity flavors with a touch of nostalgia, you’re in for a treat with Pineapple Upside Down Cupcakes. These little delights capture the essence of the classic pineapple upside-down cake but come in a convenient cupcake form. They are perfect for parties, picnics, or simply as a sweet end to any meal. With a luscious layer of caramelized pineapple and a moist, fluffy cake, these cupcakes are sure to impress everyone at your table.

Making these cupcakes is not only fun but also surprisingly simple. The combination of juicy pineapple, sweet cherries, and rich cake makes each bite a little celebration. Let’s dive into why you’ll love making and serving this recipe!

Why You’ll Love This Pineapple Upside Down Cupcake

There are several reasons why Pineapple Upside Down Cupcakes stand out among other desserts:

1. Individual Portions: Unlike traditional cakes, these cupcakes are perfectly portioned. This makes it easy to grab a cupcake and enjoy it without fuss.

2. Flavorful Layers: The sweet caramelized pineapple combined with the moist cake creates a delightful explosion of flavor. Each ingredient works in harmony to make your taste buds dance!

3. Versatile: These cupcakes can be served warm or at room temperature, making them a flexible choice for any occasion.

4. Simple Ingredients: Most of the ingredients are staples in your pantry. You won’t have to hunt for exotic items at the grocery store.

5. Fun to Make: Baking these cupcakes can be a fun activity for families and friends alike, creating memorable experiences in the kitchen.

Pineapple Upside Down Cupcakes

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• Author: Sarah Mendez
• Total Time: 40 minutes
• Yield: 12 cupcakes 1x
• Diet: Vegetarian

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Description

Pineapple Upside Down Cupcakes are a fun, mini version of the classic cake. With sweet caramelized pineapple and cherries on top of moist vanilla cake, these individual treats are as beautiful as they are delicious. Perfect for parties or a tropical-themed dessert!

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Ingredients

Scale 1x2x3x

• • Topping:
  • 1/4 cup unsalted butter, melted
  • 1/2 cup light brown sugar
  • 4–5 canned pineapple rings, drained and cut into small pieces
  • 12 maraschino cherries

 

• • Cake Batter:
  • 1 cup all-purpose flour
  • 3/4 cup granulated sugar
  • 1 tsp baking powder
  • 1/2 tsp salt
  • 1/4 cup vegetable oil
  • 1 large egg, lightly beaten
  • 1/2 cup milk
  • 1/4 cup pineapple juice (from the canned pineapple)

 

• Optional Add-Ons:
• Shredded coconut (mix into the batter or sprinkle on top)
• Chopped toasted pecans or walnuts
• A pinch of cinnamon or nutmeg for warmth

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Instructions

1. Preheat oven: to 350°F (175°C). Grease a 12-cup muffin tin well or line with cupcake liners and spray the liners with nonstick spray.
2. Prepare the topping: Spoon about 1 teaspoon of melted butter into each muffin cup. Add 1 tablespoon of brown sugar. Place a few small pieces of pineapple in each cup and top with one maraschino cherry.
3. Make the batter: In a mixing bowl, whisk together flour, granulated sugar, baking powder, and salt. In a separate bowl, whisk oil, egg, milk, and pineapple juice. Add wet ingredients to dry and stir until just combined.
4. Assemble and bake: Spoon batter evenly over the pineapple in each cup, filling about 3/4 full. Bake for 20–25 minutes, or until a toothpick inserted into the center comes out clean.
5. Cool and invert: Let cupcakes cool in the pan for 5–10 minutes. Carefully run a knife around the edges and invert onto a wire rack or tray. Let cool completely before serving.

Notes

• Don’t overfill the muffin cups—leave room for the topping to bubble up.
• Use a nonstick muffin pan or well-greased cups to make removal easier.
• These cupcakes are best served the same day they are baked but can be stored in the fridge for up to 3 days.

• Prep Time: 15 minutes
• Cook Time: 25 minutes
• Category: Dessert
• Method: Baking
• Cuisine: American

Nutrition

• Serving Size: 1 cupcake
• Calories: 210
• Sugar: 18g
• Sodium: 120mg
• Fat: 9g
• Saturated Fat: 3g
• Unsaturated Fat: 5g
• Trans Fat: 0g
• Carbohydrates: 30g
• Fiber: 1g
• Protein: 2g
• Cholesterol: 25mg

Keywords: pineapple upside down cupcakes, mini pineapple cakes, tropical cupcakes, pineapple cherry dessert

Ingredients You’ll Need for Pineapple Upside Down Cupcakes

To prepare these scrumptious cupcakes, gather the following ingredients:

Essential Ingredients

• 1/4 cup unsalted butter, melted
• 1/2 cup light brown sugar
• 4-5 canned pineapple rings, drained
• 12 maraschino cherries
• 1 cup all-purpose flour
• 3/4 cup granulated sugar
• 1 tsp baking powder
• 1/2 tsp salt
• 1/4 cup vegetable oil
• 1 large egg, lightly beaten
• 1/2 cup milk
• 1/4 cup pineapple juice

Optional Add-Ons

While this recipe is fantastic on its own, you might consider some optional variations to enhance your cupcakes:

• Coconut flakes: Adding shredded coconut to the batter can give it a tropical twist.
• Chopped nuts: Toasted pecans or walnuts can add a delightful crunch.
• Spices: A pinch of cinnamon or nutmeg could deepen the flavors and add an extra layer of warmth.

How to Make Pineapple Upside Down Cupcakes: A Step-by-Step Guide

Now, let’s go through the detailed process of making these lovely cupcakes.

Step 1: Preheat the Oven

Begin by preheating your oven to 350°F (175°C). This ensures your cupcakes bake evenly.

Step 2: Prepare the Muffin Tin

Grease a standard 12-cup muffin tin with butter or cooking spray to prevent the cupcakes from sticking.

Step 3: Create the Topping

In a small bowl, combine the melted unsalted butter and light brown sugar. Mix until well combined. Spoon a generous amount of this mixture into the bottom of each muffin cup. It will create a sweet, caramel base for your cupcakes.

Step 4: Add Pineapple and Cherries

Place one pineapple ring in each muffin cup, right on top of the butter and brown sugar mixture. Add a maraschino cherry in the center of each pineapple ring. This not only enhances the visual appeal but also adds extra sweetness.

Step 5: Prepare the Batter

In a separate mixing bowl, whisk together the all-purpose flour, granulated sugar, baking powder, and salt. This mixes up your dry ingredients to ensure even distribution.

In another bowl, combine the vegetable oil, lightly beaten egg, milk, and pineapple juice. Mix these wet ingredients thoroughly.

Step 6: Combine Ingredients

Gradually add the dry ingredients to the wet ingredients, mixing just until combined. It’s important not to overmix; a few lumps are okay. This will keep your cupcakes light and fluffy.

Step 7: Fill the Muffin Cups

Using a scoop or spoon, fill each muffin cup about two-thirds full with the batter. Be careful not to overfill, as they will rise while baking.

Step 8: Bake the Cupcakes

Place the muffin tin in the preheated oven and bake for 20-25 minutes, or until a toothpick inserted in the center comes out clean. Keep an eye on them to ensure you don’t overbake.

Step 9: Cool and Flip

Once baked, remove the cupcakes from the oven and let them cool in the pan for about 5 minutes. After that, carefully flip the muffin tin upside down on a wire rack. The cupcakes should slide out easily, revealing the beautiful pineapple and cherry topping.

Step 10: Serve

These cupcakes are best enjoyed warm but can also be served at room temperature. They make a lovely presentation on a cake stand or arranged on a platter!

Serving Suggestions for Pineapple Upside Down Cupcakes

These Pineapple Upside Down Cupcakes are delightful on their own, but here are some serving suggestions to elevate your dessert experience:

1. Whipped Cream: A dollop of fresh whipped cream on top can add a creamy texture to contrast with the sweetness of the cupcakes.

2. Ice Cream: Serve warm cupcakes with a scoop of vanilla ice cream for a delicious sundae. The warmth of the cupcakes paired with the cold ice cream creates a delightful treat.

3. Drizzle of Caramel Sauce: Drizzle some caramel sauce over the cupcakes for added sweetness and a beautiful presentation.

4. Fresh Fruit: Pair these cupcakes with slices of fresh fruit, such as strawberries or kiwi, for a refreshing touch alongside the sweet flavors of the cupcakes.

5. Coffee or Tea: Enjoy these cupcakes with a nice cup of coffee or tea. The warm flavors of the cupcake pair wonderfully with a hot beverage.

Pro Tips for Perfecting Your Pineapple Upside Down Cupcakes

To make sure your cupcakes turn out perfectly every time, consider the following tips:

1. Ingredient Temperature: Ensure that your ingredients are at room temperature. This helps the batter mix thoroughly and evenly.

2. Don’t Overmix: As mentioned earlier, avoid overmixing the batter to keep your cupcakes light and airy.

3. Use Quality Pineapple: Good quality canned pineapple will enhance the overall flavor. Look for options packed in juice rather than syrup for a fresher taste.

4. Check for Doneness: Sometimes ovens vary slightly in temperature. Check the cupcakes a few minutes before the recommended time to avoid overbaking.

5. Cool Properly: Allow the cupcakes to cool slightly before flipping them out of the pan. This helps prevent them from falling apart.

Easy Variations for Pineapple Upside Down Cupcakes

Feel free to experiment! Here are some easy variations you can try:

1. Chocolate Variation: Add cocoa powder to the dry ingredients for a chocolaty twist to the batter.

2. Spiced Version: Mix in spices like cinnamon, nutmeg, or ginger for a flavor profile that’s perfect for holidays or cooler weather.

3. Adding Coconut: Fold in coconut flakes into the batter for a tropical flair.

4. Use Other Fruits: Substitute pineapple with other fruits like peaches or cherries for a different fruity taste.

5. Gluten-Free Option: Use a gluten-free flour blend to make these cupcakes gluten-free. Check labels carefully for the best results.

Storage Tips to Store Pineapple Upside Down Cupcakes

If you happen to have leftovers (which might be unlikely!), storing your cupcakes properly is crucial to retaining their freshness:

1. Room Temperature: You can store the cupcakes at room temperature in an airtight container for up to 2 days.

2. Refrigerate: For longer storage, place the cupcakes in the refrigerator, where they can last for about a week. However, note that the texture may change slightly.

3. Freezing: You can also freeze the cupcakes. Wrap them individually in plastic wrap and place them in a freezer-safe bag. They’ll keep for up to 3 months. When you want to enjoy them, simply thaw them at room temperature or warm them in the microwave for a few seconds.

Conclusion

Pineapple Upside Down Cupcakes are not just delightful to look at; they’re a delightful burst of flavor in your mouth. With their caramelized topping and fluffy base, they bring joy to any occasion. Whether you’re celebrating a birthday, hosting a gathering, or treating yourself after a long day, these cupcakes are always a hit. So roll up your sleeves, gather your ingredients, and start baking!

FAQs About Pineapple Upside Down Cupcakes

With this recipe and all the insights shared, you’re ready to impress your friends and family with delightful Pineapple Upside Down Cupcakes. Happy baking!

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