The Sunny Pineapple Upside Down Cupcakes Recipe Everyone Loves

Memories of sweet childhood desserts dance around these delightful pineapple upside down cupcakes that blend nostalgic comfort with modern baking creativity.

Soft golden cakes nestle caramelized fruit in a compact personal portion perfect for sharing.

Tropical flavors burst through each delicate bite, creating a miniature dessert experience that feels both familiar and exciting.

Rings of caramelized pineapple crown these individual treats with rich golden-brown edges that promise incredible taste.

Buttery cake layers underneath capture classic dessert magic in a single handheld wonder.

Butter, brown sugar, and fresh pineapple combine to craft a dessert that connects generations through simple, delicious ingredients.

You’ll want to savor every remarkable morsel of these charming little cupcakes that elevate a classic recipe into something truly special.

Pineapple Upside-Down Cupcakes Special Features to Savor

• Twist Classic Dessert: Transform traditional pineapple upside-down cake into adorable, portable cupcake form that delights both kids and adults.
• Quick Crowd-Pleaser: Minimal ingredients and straightforward steps make these cupcakes perfect for spontaneous gatherings, potlucks, or weekend baking adventures.
• Sensational Flavor Combo: Caramelized pineapple and sweet cherries create a vibrant, tropical-inspired treat that brings sunshine to any table with its stunning presentation and rich taste.
• Beginner-Friendly Baking: Simple mixing technique and basic pantry ingredients ensure even novice bakers can successfully create these impressive individual desserts without stress.

Everything You Need for Pineapple Upside-Down Cupcakes

• Flour: The primary dry ingredient that provides structure to the cupcakes.
• Butter: A rich ingredient that adds moisture and flavor to the batter.
• Sugar: Provides sweetness and helps with the caramelization of the topping.
• Eggs: Bind the ingredients together and contribute to the cupcakes' texture.

• Pineapple Slices: Fresh fruit that creates a delicious caramelized layer on the bottom of the cupcakes.
• Maraschino Cherries: Bright red fruit that adds a pop of color and sweet flavor to the topping.
• Brown Sugar: Helps create a rich, caramel-like topping for the cupcakes.

• Pineapple Juice, Milk: Liquid ingredients that add moisture and enhance the cupcakes' flavor.
• Vanilla Extract: Provides a warm, sweet flavor to the cupcake batter.
• Baking Powder, Baking Soda, Salt: Essential leavening and seasoning agents that help the cupcakes rise and balance the flavors.

How to Bake Pineapple Upside-Down Cupcakes Step by Step

Step 1: Fire Up The Oven

Crank the oven to 350F (175C) and generously coat a 12-cup muffin tin with cooking spray or butter.

This ensures your cupcakes won’t stick and will slide out perfectly.

Step 2: Create Caramel Bottom

• Melted butter
• Brown sugar

Spread this sweet mixture evenly across each muffin cup.

Then artfully place a pineapple slice and a bright red maraschino cherry in the center of each compartment.

Step 3: Whip Up The Creamy Base

• Softened butter
• Granulated sugar
• Brown sugar

Whip until the mixture becomes light and airy.

Add eggs one at a time, mixing thoroughly after each addition.

Stir in vanilla extract for a rich, aromatic flavor.

Step 4: Mix Dry Ingredients

• All-purpose flour
• Baking powder
• Baking soda
• Salt

Gently fold the dry ingredients into the butter mixture, alternating with splashes of pineapple juice and milk.

Stir until just combined to keep the batter tender.

Step 5: Fill The Cups

Carefully spoon the batter over the pineapple and cherry layer, filling each cup about 3/4 full.

This allows room for the cupcakes to rise beautifully.

Step 6: Bake To Golden Perfection

Slide the muffin tin into the preheated oven and bake for 20-25 minutes.

The cupcakes are ready when a toothpick inserted comes out clean.

Let them rest in the pan for 5 minutes to set.

Step 7: Flip And Serve

Place a baking sheet over the muffin tin and quickly invert to release the cupcakes.

The pineapple and caramel topping will now be gloriously on top.

Allow cupcakes to cool completely before serving.

Tips for Fluffy and Flavorful Pineapple Cupcakes

• Use room-temperature butter for smoother, more even mixing that creates a light, fluffy cupcake texture.
• Grease the muffin tin generously with cooking spray or butter to ensure easy removal of cupcakes after baking.
• Pat pineapple slices dry with paper towels to remove excess moisture and prevent soggy cupcake bottoms.
• Gently fold ingredients until just combined to maintain a tender, soft cupcake crumb and prevent tough results.
• Position maraschino cherries carefully in the center of pineapple slices for a perfect visual presentation.

Creative Twists for Pineapple Upside-Down Cupcakes

• Gluten-Free Version: Replace all-purpose flour with gluten-free flour blend and ensure baking powder is certified gluten-free for those with wheat sensitivities.
• Dairy-Free Alternative: Swap butter with coconut oil and use almond milk instead of regular milk to create a lactose-free option.
• Tropical Remix: Substitute pineapple with mango or passion fruit slices to give a different fruity Caribbean-inspired flavor profile.
• Vegan Transformation: Use flax eggs, plant-based butter, and non-dairy milk to create a completely plant-based version of these sweet cupcakes.

Ways to Serve Pineapple Cupcakes with Style

• Tropical Brunch Companion: Pair these sweet cupcakes with a refreshing mimosa or coconut smoothie for a delightful morning treat.
• Dessert Platter Perfection: Arrange cupcakes on a beautiful serving tray with additional maraschino cherries and mint leaves for elegant presentation.
• Ice Cream Indulgence: Serve warm cupcakes alongside a scoop of vanilla or coconut ice cream for a decadent flavor combination that melts in your mouth.
• Party Crowd-Pleaser: Create mini dessert stations at gatherings, allowing guests to enjoy these portable pineapple treats with optional whipped cream topping.

Best Storage for Pineapple Upside-Down Cupcakes

• Store cupcakes in an airtight container in the refrigerator for up to 3-4 days. Cover with plastic wrap or place in a sealed container to prevent drying out.
• Wrap individual cupcakes tightly in plastic wrap, then place in a freezer bag. Freeze for up to 2 months. Label with the date to track freshness.
• Keep at room temperature for 1-2 days in a covered container. Best consumed within 24 hours for optimal taste and texture.
• Warm in microwave for 10-15 seconds or in a preheated oven at 300F for 5-7 minutes. Add a small piece of damp paper towel to prevent drying when microwaving.

FAQs

• Can I use fresh pineapple instead of canned?

Fresh pineapple works, but canned provides better consistency and moisture for the cupcakes.

• What if I don't have maraschino cherries?

You can skip them or substitute with fresh cherries or other small fruits like raspberries.

• How do I prevent the cupcakes from sticking?

Grease the muffin tin generously with butter or cooking spray and ensure even coating before adding topping.

• Is this recipe good for beginner bakers?

Yes, the recipe is straightforward with clear steps and doesn’t require advanced baking skills.

Pineapple Upside Down Cupcakes Recipe

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4.7 from 32 reviews

• Total Time: 50 minutes
• Yield: 12 1x

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Description

Scrumptious pineapple upside down cupcakes bring a delightful twist to classic desserts. Caramelized fruit and moist cake create a perfect balance of sweetness that will tempt you to savor every delectable bite.

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Ingredients

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Cupcake Base:

• 1 1/2 cups all-purpose flour
• 1/2 cup granulated sugar
• 1/2 cup brown sugar, packed
• 1/2 cup unsalted butter, softened
• 2 large eggs
• 1/2 cup pineapple juice
• 1/4 cup milk (whole or 2%)
• 1 teaspoon vanilla extract
• 1 teaspoon baking powder
• 1/2 teaspoon baking soda
• 1/4 teaspoon salt

Caramelized Topping:

• 1/4 cup unsalted butter, melted
• 1/2 cup brown sugar, packed
• 12 pineapple slices, cut to fit muffin tins
• 12 maraschino cherries

Note: All measurements are provided in both standard and American units.

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Instructions

1. Prepare the oven to 350F (175C) and generously coat a 12-cup muffin tin with non-stick spray or butter to ensure easy removal.
2. Create the caramelized base by whisking melted butter with brown sugar until smooth, then evenly distribute the mixture across each muffin cavity.
3. Arrange a single pineapple slice and a vibrant maraschino cherry at the bottom of each prepared cup, creating a colorful foundation.
4. In a large mixing bowl, cream together softened butter with granulated and brown sugars until the mixture becomes light and airy, developing a fluffy texture.
5. Incorporate eggs individually into the butter-sugar mixture, blending thoroughly after each addition, then gently fold in vanilla extract for enhanced flavor.
6. Separately, sift together flour, baking powder, baking soda, and salt to eliminate potential lumps and ensure even distribution of dry ingredients.
7. Gradually fold the dry ingredients into the wet mixture, alternating with pineapple juice and milk, stirring gently to maintain a smooth, consistent batter.
8. Carefully spoon the batter over the pineapple and cherry layer, filling each cup approximately three-quarters full to allow room for rising.
9. Bake for 20-25 minutes, monitoring until a toothpick inserted into the center emerges clean and the tops turn golden brown.
10. Allow cupcakes to rest in the tin for 5 minutes, then swiftly invert onto a baking sheet, letting the caramelized topping naturally release from the pan.
11. Let the cupcakes cool completely, allowing the flavors to settle and the caramel to set before serving.

Notes

• Perfectly grease the muffin tin with butter or cooking spray to ensure the cupcakes release smoothly without sticking.
• Use room temperature ingredients like eggs and butter to create a more uniform and fluffy batter that blends seamlessly.
• Gently fold dry ingredients into wet ingredients to maintain air bubbles and prevent dense, tough cupcakes.
• For a gluten-free version, substitute all-purpose flour with a gluten-free blend and add a pinch of xanthan gum to improve texture.

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

Nutrition

• Serving Size: 12
• Calories: 210 kcal
• Sugar: 20 g
• Sodium: 110 mg
• Fat: 9 g
• Saturated Fat: 5 g
• Unsaturated Fat: 3 g
• Trans Fat: 0 g
• Carbohydrates: 29 g
• Fiber: 1 g
• Protein: 2 g
• Cholesterol: 35 mg