The Easiest Pineapple Upside Down Cupcakes Recipe You’ll Love

Sweet, golden pineapple upside down cupcakes deliver a tropical twist to classic dessert lovers.

These delightful mini treats combine rich caramelized flavor with soft, moist cake texture.

Buttery brown sugar creates a glistening caramel base that perfectly complements tangy pineapple rings.

Each cupcake promises a burst of sunshine in every delectable bite.

Bakers of all skill levels can master this simple yet impressive dessert.

The recipe transforms ordinary ingredients into extraordinary individual desserts that spark joy.

Prepare to wow your guests with these irresistible little flavor bombs.

Easy Pineapple Upside Down Cupcakes Fun Dessert

• Rescue Dessert Moments: Whip up a nostalgic treat that transforms classic pineapple upside down cake into adorable, individual-sized cupcakes perfect for sharing.
• Simplify Baking Adventure: Create a crowd-pleasing dessert with minimal kitchen skills required, using basic pantry ingredients and straightforward mixing techniques that guarantee delicious results.
• Customize with Creativity: Swap cherries for other fruits, experiment with different cake variations, or add personal touches like a sprinkle of coconut or a drizzle of caramel to make the recipe uniquely yours.
• Crowd-Pleasing Portability: Enjoy these compact cupcakes at potlucks, family gatherings, or as a sweet afternoon snack that delivers maximum flavor in a handheld, mess-free format.

Pineapple Cupcake Ingredient Checklist

• All-Purpose Flour: A key component that provides structure for the soft and tender cupcake.
• Granulated Sugar: Adds sweetness and helps create a light texture in the cake.
• Butter: Provides rich flavor and contributes to the cake's moist crumb.
• Eggs: Bind the ingredients together and add richness to the cupcake.
• Milk: Helps create a smooth and tender cake batter.
• Vanilla Extract: Enhances the overall flavor of the cupcake.
• Vegetable Oil: Adds moisture and helps keep the cupcakes soft.

• Baking Powder: Helps the cupcakes rise and become light and fluffy.
• Salt: Balances the sweetness and enhances the overall flavor.

• Brown Sugar, Butter: Create a delicious caramelized base for the cupcakes.
• Pineapple Rings, Maraschino Cherries: Provide a classic fruity and colorful topping that adds visual appeal and flavor.

Bake Pineapple Upside Down Cupcakes Easily

Step 1: Warm Up the Oven

Get your oven ready by heating it to 350F (175C).

Grab a 12-cup muffin tin and coat it generously with cooking spray or butter to make sure nothing sticks.

Step 2: Craft the Caramel Base

• Melted butter
• Brown sugar

Stir until the mixture looks smooth and luscious.

Distribute this golden goodness evenly across each muffin cup, creating a delectable caramel foundation.

Step 3: Arrange the Fruity Centerpiece

Gently place a pineapple ring into each muffin cup, nestling it right on top of the caramel layer.

Drop a vibrant maraschino cherry right in the center of each pineapple ring for a pop of color.

Step 4: Whip Up the Cupcake Batter

• Softened butter
• Granulated sugar

Beat until the mixture becomes fluffy and light.

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

Splash in vanilla extract for extra flavor.

• All-purpose flour
• Baking powder
• Salt

Alternate adding the dry ingredients and milk to the butter mixture, starting and ending with flour.

Fold in vegetable oil to create a silky smooth batter.

Step 5: Fill and Bake

Carefully spoon the batter over the pineapple and cherries, filling each cup about three-quarters full.

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

The cupcakes are done when a toothpick inserted in the center comes out clean.

Step 6: Unmold and Cool

Let the cupcakes rest in the pan for 5 minutes.

Then, place a wire rack on top of the tin and quickly flip everything over.

The cupcakes should release with their caramelized topping intact.

Allow them to cool completely before serving up these sweet treasures.

Tips For Moist Pineapple Cupcakes

• Grease the muffin tin generously with butter or cooking spray to ensure easy removal of cupcakes without sticking.
• Choose ripe, golden pineapples for maximum natural sweetness and vibrant flavor in your cupcakes.
• Pat maraschino cherries dry with paper towels before placing them to stop them from sinking into the batter during baking.
• Use room temperature ingredients to create a smoother, more consistent batter that results in tender, even-textured cupcakes.
• Invert cupcakes immediately after baking while warm to maintain the beautiful caramelized fruit topping and prevent sticking to the pan.

Pineapple Cupcake Toppings And Mixes

• Tropical Berry Swap: Replace pineapple rings with strawberry or mango slices for a vibrant fruity alternative.
• Gluten-Free Friendly: Substitute all-purpose flour with almond or gluten-free flour blend to accommodate wheat sensitivities.
• Vegan Version: Use coconut oil instead of butter, replace eggs with flax eggs, and select plant-based milk for a dairy-free option.
• Nutty Crunch Variation: Sprinkle chopped macadamia or pecans over the caramel base before adding fruit for extra texture and richness.

Serving Pineapple Cupcakes Upside Down Style

• Tropical Brunch Star: Serve these cupcakes as a delightful centerpiece for a weekend tropical-themed brunch with fresh fruit salad and mimosas.
• Dessert Companion: Pair with vanilla bean ice cream or whipped cream for an extra decadent treat that enhances the caramelized pineapple flavor.
• Gifting Delight: Package individually in clear boxes with ribbon for a charming homemade gift that will impress friends and family at potlucks or gatherings.
• Tea Time Twist: Complement these cupcakes with a light Earl Grey tea or coconut-flavored coffee to bring out the sweet and tangy pineapple notes.

Storage For Pineapple Cupcakes Stays Fresh

• Store these delightful cupcakes in an airtight container in the refrigerator for up to 3-4 days. Cover them gently with plastic wrap or place them in a sealed container to maintain their moisture and prevent them from absorbing other food odors.
• If planning to enjoy within 1-2 days, keep the cupcakes at room temperature in a covered container. Ensure the space is cool and dry to preserve their fresh texture and prevent the caramel from becoming too sticky.
• Wrap individual cupcakes tightly in plastic wrap, then place them in a freezer-safe container or ziplock bag. Freeze for up to 2 months. Thaw overnight in the refrigerator before serving to maintain their delicious flavor and soft texture.

FAQs

• Can I use canned pineapple for this recipe?

Yes, canned pineapple rings work perfectly. Just pat them dry before placing in the muffin cups to prevent excess moisture.

• What if I don't have maraschino cherries?

You can substitute with fresh cherries or skip them entirely. The cupcakes will still taste delicious without the cherries.

• Is this recipe good for beginner bakers?

Absolutely! The steps are straightforward, and the ingredients are common. Even novice bakers can successfully make these cupcakes with clear instructions.

• Can I make these cupcakes ahead of time?

These cupcakes are best served the same day but can be stored at room temperature in an airtight container for up to 2 days without losing their quality.

Easy Pineapple Upside Down Cupcakes Recipe

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4.7 from 38 reviews

• Total Time: 45 minutes
• Yield: 12 1x

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Description

Pineapple upside down cupcakes bring tropical sunshine to classic dessert tables with delightful mini cakes. Sweet caramelized fruit tops moist golden crumb, creating perfect handheld treats that bring pure baking joy to your kitchen.

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Ingredients

Scale 1x2x3x

Main Ingredients:

• 12 pineapple rings
• 12 maraschino cherries
• 2 large eggs
• 1 1/3 cups all-purpose flour
• 1 cup granulated sugar

Wet Ingredients:

• 2/3 cup milk (5.3 fluid ounces)
• 1/4 cup vegetable oil (2 fluid ounces)
• 1/3 cup unsalted butter, softened (2.7 ounces)
• 1/2 teaspoon vanilla extract

Dry and Additional Ingredients:

• 1 1/2 teaspoons baking powder
• 1/4 teaspoon salt
• 1/4 cup unsalted butter, melted (2 ounces)
• 1/2 cup brown sugar

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Instructions

1. Preheat the oven to 350°F (175°C) and thoroughly coat a 12-cup muffin tin with non-stick spray to prevent adherence.
2. Combine melted butter and brown sugar in a mixing bowl, creating a rich caramel mixture. Distribute this evenly across the muffin compartments, establishing a sticky foundation.
3. Delicately position a single pineapple ring atop the caramel base in each cup. Nestle a vibrant maraschino cherry precisely in the center of each pineapple ring.
4. Cream butter and granulated sugar until fluffy and pale. Incorporate eggs individually, ensuring thorough integration after each addition. Introduce vanilla extract. Separately, blend flour, baking powder, and salt. Alternate adding dry ingredients and milk to the butter mixture, commencing and concluding with flour. Gently incorporate vegetable oil for enhanced moisture.
5. Carefully ladle batter over the fruit layer, filling each compartment approximately three-quarters full. Transfer to the preheated oven and bake for 20-25 minutes, monitoring until a inserted toothpick emerges clean.
6. Allow cupcakes to rest in the pan for 5 minutes, then confidently invert onto a wire rack while still warm to preserve the caramelized topping’s intricate design. Permit complete cooling before serving these miniature desserts.

Notes

• Prevent Sticking Generously grease the muffin tin with butter or cooking spray, ensuring every nook and cranny is covered to guarantee easy removal of cupcakes.
• Caramel Base Control Distribute the butter and brown sugar mixture evenly to create a consistent caramel layer that will beautifully coat each cupcake when inverted.
• Cherry Placement Position maraschino cherries precisely in the center of pineapple rings for a classic, symmetrical presentation that looks professionally made.
• Dairy-Free Adaptation Substitute milk with coconut milk or almond milk, and use vegan butter to create a delightful dairy-free version without compromising flavor or texture.

• Prep Time: 20 minutes
• Cook Time: 25 minutes
• Category: Desserts, Snacks
• Method: Baking
• Cuisine: American

Nutrition

• Serving Size: 12
• Calories: 205
• Sugar: 18 g
• Sodium: 140 mg
• Fat: 8 g
• Saturated Fat: 4 g
• Unsaturated Fat: 3 g
• Trans Fat: 0 g
• Carbohydrates: 30 g
• Fiber: 0.5 g
• Protein: 2.5 g
• Cholesterol: 40 mg