Buttery Pineapple Upside-Down Cupcakes Recipe: Sweet Mini Joys

Let me share a whimsical twist on a classic pineapple upside-down cupcakes recipe that’ll make your taste buds dance.

Sweet caramelized fruit nestles perfectly atop moist golden cake.

Memories of grandma’s kitchen swirl through each delectable bite.

Compact individual servings mean everyone gets their own little sunshine-topped treat.

Rings of sunny pineapple create a gorgeous golden crown on each miniature dessert.

Simple ingredients transform into something magical with just a few clever techniques.

Prepare to wow everyone at your next gathering with these irresistible little delights.

How to Store and Reheat Pineapple Upside-Down Cupcakes

• Store cupcakes in an airtight container in the refrigerator for up to 3 days. Wrap each cupcake individually in plastic wrap to maintain moisture and prevent them from drying out.
• Place cooled cupcakes in a freezer-safe container, separating layers with parchment paper. Freeze for up to 2 months. Thaw overnight in the refrigerator before serving.
• Warm cupcakes gently in the microwave for 10-15 seconds or in a preheated oven at 300°F for 5-7 minutes. Avoid overheating to prevent the caramelized topping from becoming tough or burnt.
• If serving within 24 hours, keep cupcakes at room temperature in a sealed container. This helps preserve their soft texture and prevents them from becoming too firm.

Great Pairings for Pineapple Upside-Down Cupcakes

• Perfect Beverage Pairing: Tropical Rum Cocktail
• Mix a light rum with pineapple juice and a splash of coconut cream to complement the cupcakes' fruity tropical flavor profile and enhance the dessert's sweetness.
• Complementary Wine Selection: Sweet Riesling
• Choose a chilled German or New York Riesling with subtle sweetness that matches the caramelized pineapple topping and balances the cupcake's rich texture.
• Gourmet Coffee Companion: Vanilla Macchiato
• Brew a smooth vanilla macchiato with espresso to cut through the cupcake's sweetness and provide a creamy, aromatic contrast that elevates the dessert experience.
• Refreshing Non-Alcoholic Option: Sparkling Pineapple Spritzer
• Create a homemade sparkling pineapple spritzer using fresh pineapple juice, seltzer water, and a hint of mint to mirror the cupcake's fruity notes while offering a light, effervescent counterpoint.

Pineapple Upside-Down Cupcake Variations

• Gluten-Free Tropical Delight: Replace pineapple cake mix with a gluten-free yellow cake mix, ensuring all ingredients are certified gluten-free for those with celiac disease or gluten sensitivities.
• Vegan Pineapple Cupcake Treat: Substitute eggs with flax eggs, use coconut oil instead of vegetable oil, and select a vegan-friendly cake mix to create a plant-based version of this classic dessert.
• Low-Sugar Hawaiian Mini Cakes: Swap brown sugar with a sugar-free alternative like stevia or monk fruit sweetener, and use a sugar-free cake mix to reduce overall sugar content for diabetic-friendly options.
• Coconut Pineapple Fusion: Add shredded coconut to the cake batter and sprinkle toasted coconut flakes on top after baking for an extra tropical flavor profile and interesting texture.

FAQs

• Can I use fresh pineapple instead of canned crushed pineapple?

Fresh pineapple works, but make sure to drain it thoroughly and chop it into small pieces to match the crushed texture of canned pineapple.

• What if I don't have a pineapple cake mix?

You can substitute with a yellow or vanilla cake mix and add 2 tablespoons of pineapple juice for extra flavor. The texture might be slightly different but still delicious.

• How do I prevent the cupcakes from sticking to the pan?

Use non-stick cooking spray generously and ensure you run a knife around the edges immediately after baking. Letting them cool for 5 minutes before inverting helps release them cleanly.

• Can I make these cupcakes ahead of time?

Yes, you can bake these cupcakes a day in advance. Store them in an airtight container at room temperature and dust with powdered sugar just before serving.

What Makes Pineapple Upside-Down Cupcakes a Treat

• Quick and Simple Creation: These cupcakes transform a classic dessert into adorable individual servings perfect for parties and gatherings.
• Foolproof Baking: Designed for all skill levels, the recipe uses convenient cake mix and minimal ingredients, making it incredibly beginner-friendly for home bakers.
• Delightful Presentation: Flipping the cupcakes reveals a gorgeous caramelized pineapple and cherry topping that looks professionally crafted with minimal effort.
• Versatile Dessert Option: Serves as an excellent treat for potlucks, family celebrations, brunch events, or casual weekend dessert cravings with its crowd-pleasing tropical flavor profile.

Pineapple Upside-Down Cupcake Must-Haves

Main Ingredients:

• Pineapple Cake Mix: Pre-mixed dry cake blend with pineapple flavor.
• Eggs: Fresh binding ingredient for cake structure.
• Vegetable Oil: Smooth moistening agent for cake batter.
• Pineapple Juice: Liquid to enhance cake flavor.

• Crushed Pineapple: Sweet tropical fruit base for cupcake topping.
• Maraschino Cherries: Bright red decorative fruit for visual appeal.
• Brown Sugar: Rich, deep sweetener for caramelized layer.

• Melted Butter: Rich ingredient for preventing sticking.
• Confectioners' Sugar: Light dusting for sweet decoration.

• Non-Stick Cooking Spray: Kitchen helper for easy cupcake removal.
• Muffin Tin: Standard baking pan with multiple cups.

Baking Pineapple Upside-Down Cupcakes

Step 1: Warm Up the Oven

Crank the oven to a toasty 350°F and get ready for some baking magic.

Step 2: Prepare Muffin Tin

Grab your muffin tin and give each cup a generous spray of non-stick cooking spray to ensure easy release later.

Step 3: Create Delicious Bottom Layer

• Drizzle melted butter
• Sprinkle brown sugar
• Place a bright red maraschino cherry in the center
• Top with well-drained crushed pineapple

Gently press the pineapple to create an even, delectable base.

Step 4: Whip Up the Cake Batter

• Pineapple cake mix
• Reserved pineapple juice
• Eggs
• Vegetable oil

Start mixing on low speed for 30 seconds to blend ingredients, then kick it up to medium speed.

Beat for 2 minutes until the batter is silky smooth.

Step 5: Fill the Cups

Pour the cake batter into each muffin cup, filling about two-thirds full.

This gives your cupcakes room to rise and become perfectly puffy.

Step 6: Bake to Perfection

Slide the muffin tin into the preheated oven and bake for approximately 20 minutes.

Check doneness by inserting a toothpick – it should come out clean when the cupcakes are ready.

Step 7: Cool and Flip

Let the cupcakes rest in the pan for 5 minutes.

Run a knife around the edges to loosen, then confidently flip the tin onto a wax paper-lined baking sheet.

Step 8: Final Flourish

For an extra touch of sweetness, dust the cupcakes with a light sprinkle of confectioners’ sugar before serving.

Smart Tips for Pineapple Upside-Down Cupcakes

• Ensure crushed pineapple is well-drained to prevent excess moisture from making cupcake bottoms soggy and compromising the texture.
• Use exact measurements for pineapple juice and ingredients to maintain the perfect balance of flavor and moisture in the cupcakes.
• Insert a toothpick in the center of cupcakes and look for a clean removal, which indicates they're perfectly baked without being dry.
• Run a knife carefully around edges to prevent tearing the caramelized topping when removing cupcakes from the pan.
• Allow cupcakes to cool completely before serving to enhance the caramelized flavor and ensure the best texture and taste.

Pineapple Upside-Down Cupcakes Recipe

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4.8 from 24 reviews

• Total Time: 40 minutes
• Yield: 12 1x

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Description

Sweet caramelized pineapple upside-down cupcakes bring tropical charm to classic dessert memories. Buttery golden cake nestles juicy fruit rings, promising delightful bites perfect for sharing with friends and family.

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Ingredients

Scale 1x2x3x

Fruits and Toppings:

• 24 maraschino cherries
• 1 (20 ounces / 567 grams) can crushed pineapple, well-drained

Sugars and Sweeteners:

• 1.5 cups brown sugar
• 0.5 cup melted butter

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Instructions

1. Prepare the oven by heating to 350°F (175°C), ensuring an ideal baking environment for the cupcakes.
2. Coat 24 muffin cups thoroughly with non-stick cooking spray, creating a smooth surface for easy removal.
3. Create a delectable base layer by drizzling melted butter into each muffin cup, establishing a rich foundation.
4. Sprinkle brown sugar over the butter, creating a caramel-like bottom that will infuse sweetness into the cupcakes.
5. Gently place a maraschino cherry at the center of each cup, adding a vibrant pop of color and flavor.
6. Distribute well-drained crushed pineapple over the cherry and brown sugar, pressing lightly to ensure an even coverage.
7. In a large mixing bowl, combine pineapple cake mix, reserved pineapple juice, eggs, and vegetable oil, blending ingredients thoroughly.
8. Initiate mixing on low speed to incorporate ingredients, then increase to medium speed for 2 minutes to achieve a smooth, consistent batter.
9. Carefully pour the batter into prepared muffin cups, filling each approximately two-thirds full to allow proper rising during baking.
10. Transfer the muffin tin to the preheated oven and bake for 20 minutes, monitoring until a toothpick inserted into the center comes out clean.
11. Remove from oven and let cupcakes rest in the pan for 5 minutes, allowing them to set and cool slightly.
12. Loosen cupcake edges using a knife, ensuring clean separation from the pan sides.
13. Invert the muffin tin onto a wax paper-lined baking sheet in one swift, confident motion to reveal the caramelized pineapple topping.
14. Optional: Dust the cupcake tops with a delicate layer of confectioners’ sugar, adding a final touch of sweetness and visual appeal.

Notes

• Drain pineapple thoroughly to prevent excess moisture that could make cupcakes soggy and compromise their texture.
• Swap standard maraschino cherries with fresh dark cherries for a more natural, less processed flavor profile.
• Use room temperature eggs to ensure smoother batter integration and more consistent cupcake rise.
• Create dairy-free version by substituting vegetable oil with coconut oil for enhanced tropical flavor complexity.

• Prep Time: 15 minutes
• Cook Time: 25 minutes
• Category: Desserts, Snacks
• Method: Baking
• Cuisine: American

Nutrition

• Serving Size: 12
• Calories: 210
• Sugar: 14 g
• Sodium: 150 mg
• Fat: 8 g
• Saturated Fat: 5 g
• Unsaturated Fat: 3 g
• Trans Fat: 0 g
• Carbohydrates: 32 g
• Fiber: 1 g
• Protein: 2 g
• Cholesterol: 30 mg