Classic Pineapple Upside-Down Cupcakes Recipe: Sweet Mini Delights

Pineapple upside-down cupcakes represent a whimsical reimagining of traditional dessert classics with a playful personal touch.

Compact and adorable, these miniature delicacies refine standard baking expectations into something magical and inviting.

Caramelized fruit refines ordinary cake into an extraordinary sensory experience that delights both eyes and palate.

Warm brown sugar creates a luscious foundation that complements the tangy tropical fruit perfectly.

Rich butterscotch undertones meld seamlessly with soft cake textures, producing an irresistible treat that sparks immediate enthusiasm.

Small yet sophisticated, these cupcakes elevate home baking into an artistic expression of culinary creativity.

Sweet memories come alive with each delectable bite that promises pure indulgence.

Why These Mini Upside-Down Cakes Win Big on Flavor

• Capture Tropical Delight: Savor the exotic burst of pineapple flavor that transforms ordinary cupcakes into a sunshine-filled treat, bringing a slice of tropical paradise to your dessert table.
• Effortless Elegance: Whip up these stunning cupcakes with minimal effort, using a simple cake mix and clever technique that creates a show-stopping presentation without complex baking skills.
• Versatile Party Pleaser: Perfect for gatherings, potlucks, or family celebrations, these individual-sized desserts offer a convenient and crowd-pleasing option that looks impressive yet requires minimal preparation time.
• Nostalgic Comfort Twist: Reimagine the classic pineapple upside-down cake in a cute, portable cupcake format that delivers all the beloved caramelized flavors and moist texture of the traditional dessert.

What Goes Into These Pineapple-Topped Cupcake Beauties

• Pineapple Cake Mix: Provides the primary cake structure with convenient pineapple flavor and easy preparation.
• Eggs: Bind ingredients together and create a light, fluffy texture.
• Vegetable Oil: Ensures moisture and softness in the cupcake.
• Pineapple Juice: Enhances cake flavor and adds moisture to the batter.

• Melted Butter: Creates a rich, golden base for the caramelized topping.
• Brown Sugar: Develops a deep caramel flavor and helps create a sticky, sweet layer.
• Maraschino Cherries: Adds a pop of color and classic sweet-tart flavor.
• Crushed Pineapple: Provides fruity moisture and traditional upside-down cake texture.

• Confectioners Sugar: Offers a delicate, sweet dusting for visual appeal and extra sweetness.

How to Flip Out Perfectly Sweet and Sticky Cupcakes

Step 1: Prepare the Oven and Muffin Cups

Preheat the oven to 350°F (175°C). Coat 24 muffin cups thoroughly with cooking spray.

Step 2: Create the Caramel Pineapple Base

• Add melted butter
• Sprinkle brown sugar over the butter
• Place 1 maraschino cherry in the center
• Spread crushed pineapple evenly over the cherry

Step 3: Mix the Cake Batter

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

Blend ingredients starting on low speed for 30 seconds, then increase to medium speed for 2 minutes until smooth.

Step 4: Fill the Muffin Cups

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

Step 5: Bake the Cupcakes

Bake in the preheated oven for 20 minutes. Check doneness by inserting a toothpick into the center – it should come out clean.

Step 6: Cool and Release the Cupcakes

Let cupcakes cool in the pan for 5 minutes. Run a knife around the edges to loosen. Carefully flip onto a wax paper-lined baking sheet.

Step 7: Add a Finishing Touch

Dust the cupcakes with a light sprinkle of confectioners’ sugar just before serving for extra sweetness and elegant presentation.

Tips to Nail That Golden Pineapple Caramel Top

• Butter Up the Pan: Use non-stick cooking spray generously to ensure easy cupcake removal and prevent sticking.
• Arrange Cherries Carefully: Place maraschino cherries precisely in the center for a picture-perfect presentation that impresses every time.
• Mix with Precision: Start mixing on low speed to incorporate ingredients smoothly, preventing lumps and creating a silky cake batter.
• Check for Doneness: Test cupcakes with a toothpick inserted in the center; it should come out clean to guarantee perfectly baked treats.
• Cool and Release Gently: Let cupcakes rest in the pan for exactly five minutes before carefully loosening edges with a knife for a flawless flip.

Store Like a Pro, So They Stay Just as Pretty

• Storage: Place leftover cupcakes in an airtight container with a tight-fitting lid to maintain moisture and prevent drying out. Seal the container completely to keep the pineapple topping fresh and prevent absorbing other refrigerator odors.
• Refrigeration: Store cupcakes in the refrigerator for up to 3-4 days. Keep them in a single layer to protect the delicate caramelized pineapple topping from getting crushed or damaged.
• Reheating: Warm refrigerated cupcakes gently in the microwave for 10-15 seconds to restore their soft texture. For best results, let cupcakes sit at room temperature for 15 minutes before serving to enhance their flavor and ensure a tender crumb.

What to Pair with These Tropical Dessert Gems

• Brew Sweet Tropical Cocktail Companion: Pair these cupcakes with a chilled piña colada or a light rum-based mojito to enhance the pineapple's tropical essence and complement the dessert's caramelized sugar notes.
• Serve Creamy Contrast Partner: Offer a scoop of vanilla bean ice cream or freshly whipped cream alongside the cupcakes, creating a cool, smooth contrast to the warm, sticky-sweet cake texture.
• Match Complementary Coffee Sidekick: Select a medium roast Colombian coffee or a vanilla-infused espresso to balance the dessert's sweetness and provide a rich, aromatic backdrop that highlights the pineapple's bright flavor profile.
• Elevate Sparkling Wine Pairing: Uncork a crisp prosecco or slightly sweet moscato to cut through the richness of the cupcakes, adding a bubbly, refreshing element that cleanses the palate between bites.

Flavor Ideas That Bring the Island Vibes

• Tropical Coconut Crunch: Sprinkle toasted coconut flakes over the cupcakes after flipping, adding a delightful crunch and extra island flavor to the classic recipe.
• Rum-Infused Caramel: Replace part of the pineapple juice with dark rum in the cake mix for a more sophisticated adult version, creating a rich caramel undertone.
• Nutty Pineapple Paradise: Mix chopped macadamia nuts into the batter or sprinkle them on top before baking, introducing a buttery, tropical texture to the cupcakes.
• Spiced Tropical Treat: Incorporate a pinch of ground cinnamon and nutmeg into the cake mix, giving the cupcakes a warm, aromatic dimension that complements the sweet pineapple.

Pineapple Upside-Down Cupcakes Recipe

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4.5 from 34 reviews

• Total Time: 40 minutes
• Yield: 24 1x

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Description

Pineapple Upside-Down Cupcakes bring classic retro charm to modern dessert tables with individual-sized nostalgia. Sweet caramelized pineapple tops moist vanilla cake, creating a delightful twist on traditional skillet-baked treats that will make you crave another bite.

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Ingredients

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Main Ingredients:

• 1 package (18.25 ounces / 517 grams) pineapple cake mix
• 3 large eggs
• ½ cup vegetable oil
• 1 ½ cups reserved pineapple juice

Topping Ingredients:

• ½ cup melted butter
• 1 ½ cups brown sugar
• 1 can (20 ounces / 567 grams) crushed pineapple, well-drained
• 24 maraschino cherries

Optional Finishing Ingredient:

• 1 tablespoon confectioners’ sugar for dusting

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Instructions

1. Preheat the oven to 350°F (175°C) and generously coat 24 muffin cups with non-stick cooking spray, ensuring complete coverage.
2. Drizzle of melted unsalted butter into each muffin cup, then sprinkle of brown sugar evenly across the butter layer. Gently place a maraschino cherry at the center of each cup and carefully distribute crushed pineapple around it, pressing softly to create an even, attractive base.
3. In a large mixing bowl, combine the pineapple cake mix, reserved pineapple juice, large eggs, and vegetable oil. Blend the ingredients using an electric mixer, beginning at low speed for 30 seconds to incorporate, then increasing to medium speed for 2 minutes until the batter becomes smooth and well-integrated.
4. Distribute the prepared batter evenly among the muffin cups, filling each approximately two-thirds full to allow room for rising during baking.
5. Transfer the muffin tins to the preheated oven and bake for 18-22 minutes, checking doneness by inserting a toothpick into the center of a cupcake – it should emerge clean with no wet batter attached.
6. Remove from the oven and let the cupcakes rest in the pan for 5 minutes. Carefully run a knife around the edges to loosen, then invert onto a wax paper-lined baking sheet, allowing the pineapple and cherry topping to settle naturally.
7. Before serving, optionally dust the cupcakes with a light sprinkle of confectioners’ sugar for an elegant finishing touch and added sweetness.

Notes

• Flip the cupcakes immediately after baking to prevent sticking and maintain the beautiful caramelized topping’s intricate design.
• Ensure pineapple pieces are thoroughly drained to avoid excess moisture that could compromise the cupcake’s texture.
• Room temperature ingredients blend more smoothly, creating a more consistent and tender cake batter.
• Store leftover cupcakes in an airtight container at room temperature for maximum freshness, consuming within 2-3 days.
• Customize the recipe by substituting maraschino cherries with fresh dark cherries for a more natural, vibrant flavor profile.
• Cold ingredients can create lumpy batter, so let eggs and juice sit out 30 minutes before mixing for optimal results.

• Prep Time: 20 minutes
• Cook Time: 20 minutes
• Category: Desserts, Snacks
• Method: Baking
• Cuisine: American

Nutrition

• Serving Size: 24
• Calories: 228 kcal
• Sugar: 20g
• Sodium: 265mg
• Fat: 10g
• Saturated Fat: 2g
• Unsaturated Fat: 7g
• Trans Fat: 0g
• Carbohydrates: 34g
• Fiber: <1g
• Protein: 3g
• Cholesterol: 37mg