The Sweetest Pineapple Upside-Down Cupcakes Recipe Ever Made

Sweet, golden pineapple upside-down cupcakes bring a nostalgic twist to a classic dessert that melts in your mouth.

These miniature treats capture the essence of traditional comfort baking with a modern, portable spin.

Caramelized pineapple rings nestled atop soft, buttery cake create a stunning visual and flavor experience.

Each bite bursts with tropical sweetness and rich, moist texture that makes these cupcakes irresistible.

The combination of juicy pineapple and tender cake delivers a perfect balance of flavors that dance on your palate.

Compact yet decadent, these cupcakes are ideal for parties, potlucks, or a delightful afternoon treat.

Let’s find out this delectable recipe and watch as these little wonders become the star of your dessert lineup.

How to Store Pineapple Upside-Down Cupcakes

• Quick Refrigeration Strategy: Store cupcakes in an airtight container inside the refrigerator for maximum freshness, ensuring they stay moist and delicious for up to 4 days without losing their delightful texture.
• Room Temperature Tip: Let cupcakes sit at room temperature for 15-20 minutes before serving to enhance their softness and bring out the rich caramelized pineapple flavor.
• Freezing Technique: Wrap individual cupcakes in plastic wrap, then place in freezer-safe containers to maintain quality for up to 3 weeks – perfect for make-ahead dessert lovers who want a quick sweet treat.
• Make-Ahead Magic: Prepare the batter and topping a day in advance, storing them separately in the refrigerator to streamline your baking process and save precious morning preparation time.

Quick Recipe Overview

Prep Time: 20 minutes

Cook Time: 20 minutes

Total Time: 40 minutes

Calories: 290 kcal

Servings: 25

What Goes Into Pineapple Upside-Down Cupcakes

• Pineapple Cake Mix: Convenient shortcut that ensures tropical flavor and perfect texture for cupcakes.
• Eggs: Provides structure, richness, and helps bind ingredients together.
• Vegetable Oil: Adds moisture and ensures tender, soft cupcake crumb.

• Crushed Pineapple: Delivers intense fruity flavor and natural sweetness to the cupcake base.
• Maraschino Cherries: Brings vibrant color, sweet-tart taste, and classic retro presentation.
• Melted Butter: Creates rich, golden caramelization and enhances overall flavor depth.
• Brown Sugar: Generates deep, molasses-like sweetness and helps create signature sticky topping.

• Confectioners' Sugar: Optional light dusting adds elegant visual appeal and subtle sweetness.

• Choose well-drained pineapple to prevent excess moisture in cupcakes.
• Use fresh, room-temperature eggs for better mixing and rising.
• Select ripe, bright red maraschino cherries without blemishes.
• Opt for dark brown sugar for more intense caramel flavor.

Tools to Make Pineapple Upside-Down Cupcakes

• Large mixing bowl: Essential for combining cake mix and wet ingredients smoothly.
• Muffin tin: Holds 24 cupcakes and creates perfect individual portions.
• Measuring cups and spoons: Precise for measuring pineapple juice, eggs, and oil.
• Electric mixer: Helps blend cake batter thoroughly and evenly.
• Toothpick: Checks cupcake doneness by testing center for clean insertion.
• Wax paper: Prevents sticking when inverting cupcakes after baking.
• Small knife: Helps loosen cupcakes from muffin tin edges.
• Cooking spray: Ensures easy cupcake removal and prevents sticking.
• Baking sheet: Supports cupcakes when flipping and catching any drips.
• Sifter or fine strainer: Optional for dusting confectioners' sugar on top.

How to Bake Pineapple Upside-Down Cupcakes

• Oven Preparation Warm up the kitchen with an inviting 350°F temperature and coat muffin tins with a light cooking spray.
• Sweet Caramel Foundation Create a delectable base by drizzling melted butter into each cup, sprinkle brown sugar, nestle a vibrant cherry in the center, and gently spread crushed pineapple for a luscious bottom layer.
• Batter Blending Combine cake mix with pineapple juice, eggs, and vegetable oil in a mixing bowl. Whip the ingredients until they transform into a silky smooth mixture, starting slow and then building momentum.
• Filling Cupcake Cavities Gracefully pour the golden batter into muffin cups, filling each about two-thirds full to ensure perfect rising and beautiful rounded tops.
• Baking Transformation Place the tray in the heated oven and let the magic happen for approximately 20 minutes, watching for a clean toothpick test signaling these tropical treats are ready.
• Cooling and Releasing Gently let the cupcakes rest in the pan for five minutes, then carefully flip them onto a waiting surface, allowing the caramelized pineapple to create a stunning topping.
• Final Flourish Dust these delightful treats with a light snowfall of powdered sugar, transforming them into a true dessert showstopper.

Pineapple Cupcake Tips for Sweet Results

• Elevate Your Cupcake Game
• Replace maraschino cherries with fresh, pitted dark cherries for a more natural, vibrant flavor profile that adds gourmet flair to your dessert.
• Drain pineapple thoroughly to prevent excess moisture, ensuring your cupcakes remain perfectly fluffy and prevent potential soggy bottoms.
• Sprinkle toasted coconut flakes or chopped macadamia nuts on top for a Hawaiian-inspired crunch that complements the tropical pineapple essence.
• These cupcakes can be stored in an airtight container at room temperature for up to three days, making them perfect for advance party preparation or weekend baking.

Serving Pineapple Upside-Down Cupcakes Perfectly

• Tropical Brunch Companion: Pair these delightful cupcakes with a fresh coconut smoothie or passion fruit mimosa for a vibrant breakfast experience.
• Elegant Dessert Platter: Arrange cupcakes on a beautiful serving tray with scattered fresh pineapple chunks and mint leaves for a stunning visual presentation that screams tropical elegance.
• Afternoon Tea Treat: Serve alongside light cream cheese spread or whipped vanilla mascarpone, allowing guests to add a dollop of extra creaminess to each cupcake bite.
• Summer Party Centerpiece: Create a colorful dessert station by clustering these cupcakes on tiered stands, surrounded by tropical flowers and small cocktail umbrellas for a playful, festive touch.

Delightful Pineapple Upside-Down Cupcakes Recipe

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4.6 from 24 reviews

• Total Time: 40 minutes
• Yield: 25 1x

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Description

Scrumptious pineapple upside-down cupcakes blend nostalgic flavors with modern baking charm. Caramelized fruit tops moist cake, creating a delightful dessert you’ll savor with pure pleasure.

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Ingredients

Scale 1x2x3x

• 1 package (18.25 oz / 517 g) pineapple cake mix
• 3 large eggs
• ½ cup vegetable oil
• 1 ½ cups reserved pineapple juice
• ½ cup melted butter
• 1 ½ cups brown sugar
• 1 can (20 oz / 567 g) crushed pineapple, well-drained
• 24 maraschino cherries
• 1 tbsp confectioners’ sugar for dusting

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Instructions

1. Preparation: Warm the oven to 350°F (175°C) and thoroughly coat 24 muffin cups with non-stick spray, ensuring complete surface coverage.
2. Base Creation: Generously layer melted butter and brown sugar into each muffin cup. Position a maraschino cherry at the center, surrounding it with crushed pineapple, gently pressing to create an attractive, even foundation.
3. Batter Mixing: Combine pineapple cake mix, pineapple juice, eggs, and vegetable oil in a large mixing bowl. Utilize an electric mixer to blend ingredients, starting at low speed for 30 seconds, then increasing to medium for 2 minutes until achieving a silky, homogeneous consistency.
4. Filling and Baking: Evenly distribute batter into muffin cups, filling approximately two-thirds full. Transfer to preheated oven and bake for 18-22 minutes, verifying doneness by inserting a toothpick that comes out clean.
5. Cooling and Presentation: Allow cupcakes to rest in the pan for 5 minutes, then carefully loosen edges with a knife. Invert onto a wax paper-lined baking sheet, permitting the pineapple and cherry topping to settle naturally. Optionally dust with confectioners’ sugar before serving for an elegant finish.

Notes

• Butter Distribution Technique: Evenly spread melted butter to create a rich, caramelized base that prevents sticking and enhances flavor.
• Cherry Placement Strategy: Center the maraschino cherry carefully to ensure a visually appealing and symmetrical presentation in each cupcake.
• Mixing Speed Matters: Start mixing at low speed to incorporate ingredients, then increase to medium for a smooth, well-blended batter without overmixing.
• Inversion Timing: Allow cupcakes to rest 5 minutes before inverting to help the topping set and prevent breaking delicate caramelized layers.

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

Nutrition

• Serving Size: 25
• Calories: 290
• Sugar: 30 g
• Sodium: 300 mg
• Fat: 14 g
• Saturated Fat: 6 g
• Unsaturated Fat: 7 g
• Trans Fat: 0 g
• Carbohydrates: 38 g
• Fiber: 1 g
• Protein: 3 g
• Cholesterol: 40 mg