A Sweet & Sunny Mini Dessert That Flips Classic Flavor Upside Down

These Pineapple Upside Down Cupcakes bring all the tropical charm of a full-sized pineapple upside-down cake into individual servings. With caramelized brown sugar topping, a juicy pineapple ring, and a soft buttery crumb—they’re a sweet, nostalgic treat perfect for birthdays, tea time, or any occasion that calls for something special.

A classic dessert made mini and magical!


Why You’ll Love This Recipe:

  • 🍰 Perfect Portions: Easy to serve and eat—no slicing required.
  • 🍍 Tropical Touch: Pineapple brings natural sweetness and moisture in every bite.
  • ⏱️ Quick Bakes: Ready from bowl to oven in under 30 minutes.
  • 🧁 No Fancy Tools Needed: Just a muffin tin and canned pineapple—pantry-friendly and easy.
  • ❄️ Freezer-Friendly: These cupcakes keep well frozen and reheat like new.

Ingredients (Makes 12 cupcakes):

For the Topping:

  • ¼ cup (½ stick) unsalted butter , melted (or coconut oil for vegan option)
  • ½ cup light brown sugar
  • 4–5 canned pineapple rings , drained (use extra juice for the batter if needed)
  • 12 maraschino cherries (for that classic center pop of color and flavor)

For the Cake Batter:

  • 1 cup all-purpose flour
  • ¾ cup granulated sugar
  • 1 tsp baking powder
  • ½ tsp salt
  • ¼ cup vegetable oil (or melted coconut oil)
  • 1 large egg , lightly beaten
  • ½ cup milk (dairy or plant-based)
  • ¼ cup pineapple juice (from the can – adds extra moisture and flavor)

Instructions:

Step 1: Preheat Oven & Prep Muffin Tin

Preheat oven to 350°F (175°C) .

Grease a 12-cup muffin tin with cooking spray or butter.

Or use paper liners for easier release—but skip them if you prefer flipping the cakes out warm.


Step 2: Make the Caramelized Topping

In a small bowl, mix:

  • Melted butter
  • Brown sugar

Spoon an even amount into each muffin cup—about 1 tbsp per liner .

Place one pineapple ring into each cup.

Add a maraschino cherry in the center of each pineapple ring.

Set aside while preparing the batter.


Step 3: Mix the Cake Batter

In a mixing bowl, whisk together:

  • Flour
  • Granulated sugar
  • Baking powder
  • Salt

In another bowl, combine:

  • Vegetable oil
  • Egg
  • Milk
  • Pineapple juice

Mix wet ingredients until smooth.

Gradually add the dry mixture to the wet ingredients, stirring gently until just combined.

Don’t overmix—the batter should be slightly thick and pourable.


Step 4: Fill & Bake the Cupcakes

Using a spoon or ice cream scoop, fill each muffin cup two-thirds full with batter.

Make sure not to overflow the pineapple layer.

Bake at 350°F (175°C) for 20–25 minutes , or until a toothpick comes out clean.

Let cool in the pan for 5 minutes , then carefully flip onto a wire rack to fully cool.

Tip: Place a tray beneath the muffin tin when baking—it catches any bubbly caramel spills!


Step 5: Serve Warm & Golden

Enjoy these cupcakes warm or at room temperature .

They’re best eaten within the first few hours while the pineapple is still juicy and tender.

Each bite delivers:

  • The rich, golden caramelized top
  • Moist, buttery cake bottom
  • And that nostalgic hit of tropical sweetness

Tips for Success:

  • 🥣 Use Room-Temperature Egg & Milk: Prevents lumps and ensures even texture.
  • 🍑 Cherry Swap Option: Skip the maraschino cherry or replace with dried cranberries for variation.
  • 🧁 Add Nuts: Chopped pecans or walnuts add crunch on top before baking.
  • 🌿 Spice It Up: Add a pinch of nutmeg or cinnamon to the batter for extra warmth.
  • ❄️ Make Ahead Magic: Store cooled cupcakes in an airtight container for up to 2 days—or freeze for future treats.

Serving Suggestions:

  • Perfect at baby showers, brunches, or family gatherings.
  • Great with coffee, tea, or a glass of cold milk.
  • Ideal as part of a dessert buffet or boxed lunch surprise.

Nutritional Information (per cupcake, makes 12 servings – approximate):

(Without optional toppings – regular ingredients)

  • Calories: ~180 kcal
  • Protein: ~2g
  • Carbohydrates: ~25g
  • Fat: ~9g
  • Fiber: ~0.5g
  • Sugar: ~16g

These Pineapple Upside Down Cupcakes prove that sometimes the smallest desserts make the biggest impression. With their caramelized fruit topping, tender cake base, and hint of pineapple joy—they’re a must-bake whenever you want a taste of sunshine.

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