These Pineapple Upside-Down Cupcakes bring the classic flavors of pineapple upside-down cake into a fun, bite-sized treat. With a caramelized brown sugar base, sweet pineapple slices, and a moist yellow cake topping, these cupcakes are as adorable as they are delicious. Perfect for parties, potlucks, or a sweet weekend treat, they’re sure to delight everyone!


Why You’ll Love This Recipe:

  • Miniature Magic: All the flavor of a full-sized cake in a cute, single-serving size.
  • Easy & Fun: Simple ingredients and steps make this recipe perfect for bakers of all skill levels.
  • Customizable: Add maraschino cherries for a pop of color or experiment with different fruits like peaches or mangoes.

 Ingredients:

For the Pineapple Topping:

  • 1 can (20 oz) sliced pineapple , drained (reserve the juice ) 🍍
  • 1/3 cup butter , melted 🧈
  • 2/3 cup packed brown sugar 🫚
  • 12 maraschino cherries , halved (optional, for garnish ) 🍒

For the Cake Batter:

  • 1 box yellow cake mix 🍰
  • 1/2 cup vegetable oil 🫒
  • 3 large eggs 🥚
  • Reserved pineapple juice (about 1/2 cup, adjust as needed per cake mix instructions )

 Instructions:

Step 1: Preheat the Oven 🔥

  1. Preheat your oven to 350°F (175°C) .
  2. Line a muffin tin with cupcake liners or grease it lightly to prevent sticking.

Step 2: Prepare the Pineapple Topping 🍍

  1. Drain the canned pineapple slices, reserving the juice for the cake batter. Pat the slices dry with paper towels if needed.
  2. Melt the butter in a microwave-safe bowl.
  3. Sprinkle 1–2 teaspoons of brown sugar evenly into the bottom of each cupcake liner.
  4. Place a pineapple slice (or smaller pieces if needed) on top of the brown sugar in each liner. If using, place a maraschino cherry half in the center of each pineapple slice.

Step 3: Prepare the Cake Batter 🥄

  1. In a large mixing bowl, combine the yellow cake mix , vegetable oil , eggs , and reserved pineapple juice (use the amount specified on the cake mix box, typically about 1/2 cup ).
  2. Mix until the batter is smooth and well combined.

Step 4: Assemble the Cupcakes 🫕

  1. Spoon the cake batter over the pineapple slices and brown sugar, filling each liner about two-thirds full . Be careful not to overfill, as the batter will rise during baking.

Step 5: Bake the Cupcakes 🍳

  1. Place the muffin tin in the preheated oven and bake for 20–25 minutes , or until a toothpick inserted into the center of a cupcake comes out clean.
    • Tip: Rotate the pan halfway through baking for even cooking.

Step 6: Cool and Flip 🔄

  1. Allow the cupcakes to cool in the tin for 5–10 minutes .
  2. Carefully invert the cupcakes onto a serving platter or cooling rack. The brown sugar and pineapple slices will now be on top, creating a beautiful caramelized topping.

Tips for Success:

  • Add Extra Flavor: Stir a teaspoon of vanilla extract into the cake batter for an extra hint of sweetness.
  • Experiment with Fruits: Try using peach slices, mango chunks, or even mandarin oranges instead of pineapple for a unique twist.
  • Storage: Store the cooled cupcakes in an airtight container at room temperature for up to 2 days or in the refrigerator for up to 5 days .
  • Freeze Option: Freeze the cupcakes (without the topping) in a freezer-safe container for up to 2 months . Thaw overnight in the refrigerator before serving.

Nutritional Information (per cupcake, makes 12):

  • Calories: ~220
  • Protein: ~2g
  • Carbohydrates: ~35g
  • Fat: ~9g

Enjoy these Pineapple Upside-Down Cupcakes as a fun, tropical twist on a classic dessert. Their sweet, caramelized topping and moist cake make them irresistible, while their mini size adds a touch of whimsy to any occasion. Whether you’re hosting a party or simply craving something sweet, these cupcakes are sure to bring smiles all around!

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