Pineapple Upside Down Cupcakes

Name: Pineapple Upside-Down Cupcakes
Total Time: 1 hour 15 minutes (Prep: 25 mins, Cook: 22-25 mins, Cooling: 20 mins)
Servings: 12 cupcakes
Difficulty: Easy
Dietary Tags: Classic Dessert, Potluck Favorite

Introduction

Capture the nostalgic, sun-drenched charm of the classic 1950s dessert in perfectly portable form with these Pineapple Upside-Down Cupcakes. This recipe reimagines the beloved skillet cake into delightful individual portions, each one a miniature masterpiece featuring a caramelized brown sugar and butter topping, a sweet ring of pineapple, a jewel-like maraschino cherry, and a tender, buttery vanilla cake base. Ideal for parties, potlucks, or any occasion demanding a touch of retro flair, these cupcakes deliver the iconic flavor combination in a fun, shareable, and mess-free format. They are as delightful to look at as they are to eat, guaranteed to bring a smile and a wave of warm nostalgia with every single bite.

Equipment Needed

• Standard 12-cup muffin tin

• Cupcake liners (optional, but highly recommended for easiest removal)

• Large mixing bowl

• Medium mixing bowl

• Electric hand mixer or stand mixer

• Measuring cups and spoons

• Small saucepan

• Toothpick or cake tester

• Cooling rack

• Small spoon or offset spatula

Ingredients

For the Pineapple-Caramel Topping:

• ⅓ cup (75g) unsalted butter

• ⅔ cup (145g) packed light brown sugar

• 12 rings canned pineapple (about 1 x 20 oz can, in juice, not syrup)

• 12 maraschino cherries, well-drained and patted dry

For the Vanilla Buttermilk Cake:

• 1 ½ cups (190g) all-purpose flour, spooned and leveled

• 1 ½ teaspoons baking powder

• ¼ teaspoon baking soda

• ½ teaspoon salt

• ½ cup (115g) unsalted butter, softened to room temperature

• ¾ cup (150g) granulated sugar

• 2 large eggs, at room temperature

• 2 teaspoons pure vanilla extract

• ½ cup (120ml) buttermilk, at room temperature

  • Buttermilk Substitute: No buttermilk? Mix ½ cup whole milk with 1 ½ teaspoons white vinegar or lemon juice. Let sit for 5-10 minutes before using.

Instructions

Phase 1: Prepare the Pineapple-Caramel Topping

Time: 15 minutes | Intensity: Low-Medium (requires attention)

1. Prep: Preheat your oven to 350°F (175°C). Line a 12-cup muffin tin with cupcake liners. This is crucial for easy inversion later.

2. Create Caramel: In a small saucepan over medium heat, melt the ⅓ cup of butter. Add the packed brown sugar and stir constantly with a wooden spoon or heatproof spatula until the mixture is bubbling, smooth, and the sugar has fully dissolved, about 3-4 minutes. Do not boil for too long. Immediately remove from heat.

3. Assemble Toppings: Spoon 1 heaping teaspoon of the warm caramel mixture into the bottom of each cupcake liner. Swirl the pan to coat the bottom lightly. Place one pineapple ring flat in the bottom of each cup over the caramel. Place one maraschino cherry in the center of each pineapple ring. Set the pan aside while you make the batter.

Phase 2: Make the Vanilla Buttermilk Cake Batter

Time: 10 minutes | Intensity: Low (with a mixer)

1. Combine Dry Ingredients: In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.

2. Cream Butter and Sugar: In a large bowl using an electric mixer fitted with the paddle attachment, beat the softened butter and granulated sugar together on medium-high speed until light, fluffy, and pale in color, about 2-3 minutes.

3. Add Eggs and Vanilla: Add the eggs one at a time, beating well after each addition and scraping down the sides of the bowl as needed. Beat in the vanilla extract.

4. Combine Wet and Dry: With the mixer on low speed, add the dry ingredients in three parts, alternating with the buttermilk in two parts, beginning and ending with the dry ingredients. Mix each addition until just combined. Do not overmix. The batter will be thick and smooth.

Phase 3: Assemble and Bake

Time: 25 minutes | Intensity: Low (Oven does the work)

1. Fill the Cups: Using a large spoon or cookie scoop, divide the cake batter evenly among the 12 prepared muffin cups, spooning it directly over the pineapple and cherry. Fill each cup about ¾ full, gently smoothing the tops.

2. Bake: Place the muffin tin in the preheated oven. Bake for 22-25 minutes, or until the tops of the cupcakes are lightly golden and a toothpick inserted into the center of the cake (not the pineapple) comes out clean or with a few moist crumbs.

3. Cool Slightly: Remove the pan from the oven and place it on a wire cooling rack. Let the cupcakes cool in the pan for exactly 10 minutes. This allows the topping to set slightly but remain warm and pliable.

Phase 4: The Grand “Upside-Down” Reveal

Time: 5 minutes | Intensity: Low-Medium (requires confidence!)

1. Invert: After the 10-minute cooling period, place a second cooling rack or a large baking sheet over the top of the muffin tin. Wearing oven mitts, firmly grasp both the tin and the rack and quickly and confidently flip them over in one smooth motion.

2. Release: Gently lift the muffin tin away. The cupcakes should release easily, especially with the liners. If any caramel or pineapple sticks, use a small spoon to gently loosen it and place it back on the cake.

3. Peel and Cool: Carefully peel away the cupcake liners while the caramel is still slightly warm. Allow the cupcakes to cool completely on the rack, about 20-30 minutes, for the caramel to fully set.

Phase 5: Serve and Enjoy

Time: 2 minutes | Intensity: Low
Serve the cupcakes as is, or for an extra touch of decadence, add a dollop of freshly whipped cream or a scoop of vanilla ice cream alongside. The caramel will be slightly sticky, gloriously shiny, and packed with buttery, pineapple flavor.

Recipe Notes

• The Liner Lifesaver: Using liners is the single best trick for perfect, stress-free upside-down cupcakes. It prevents the sticky caramel from fusing to the pan. Parchment liners work exceptionally well.

• Room Temperature is Key: Using room temperature eggs, butter, and buttermilk ensures your batter emulsifies properly, creating a lighter, more tender crumb.

• Don’t Overbake: Start checking at 22 minutes. An overbaked cupcake will be dry. The toothpick test in the cake portion is your best guide.

• The Flip Timing: The 10-minute cooling window is critical. Too soon, and the cupcakes may fall apart; too long, and the caramel will harden and stick.

• Fresh Pineapple Option: You can use fresh pineapple rings, but they must be very ripe and sweet. Simmer them in the caramel mixture for 2-3 minutes first to soften and infuse flavor.

• Make Ahead & Storage: Store completely cooled cupcakes in a single layer in an airtight container at room temperature for up to 2 days. For longer storage, freeze unfrosted cupcakes for up to 2 months. Thaw at room temperature.

Nutrition Information (Per 1 cupcake)

Nutritional values are approximate and can vary based on specific brands of ingredients, exact pineapple ring size, and any additional toppings. This is a celebratory dessert best enjoyed in moderation.