Pineapple Upside Down Cupcakes Recipe -

Pineapple Upside Down Cupcakes Recipe

Pineapple Upside Down Cupcakes offer a charming and delightful twist on the classic Pineapple Upside Down Cake. These individual-sized treats encapsulate the same ir

resistible combination of caramelized pineapple and cherries, but in a more convenient and portion-controlled form. Perfect for gatherings, afternoon tea, or as a sweet treat after dinner, these cupcakes are sure to impress with their unique presentation and exquisite taste.



  • ½ cup sweet cream butter, melted
  • 1 ½ cups light brown sugar
  • 24 maraschino cherries
  • 1 can (20 oz) crushed pineapple
  • 1 package (18.25 oz) pineapple cake mix
  • 3 large eggs
  • 1 ½ cups pineapple juice
  • ½ cup canola oil
  • 1 tablespoon powdered sugar, for garnish



Step 1: Preheat the Oven and Prepare the Muffin Tin
Start by preheating your oven to 350°F (175°C). Take a muffin tin and grease it well. This preparation is crucial to ensure that the cupcakes can be easily removed after baking.

Step 2: Create the Pineapple and Cherry Base
In each muffin cup, pour a small amount of melted sweet cream butter, ensuring the base is evenly covered. Add a layer of light brown sugar over the butter in each cup. This will create the caramelized topping once inverted. Place a single maraschino cherry in the center of each muffin cup, on top of the sugar layer. Then, spoon crushed pineapple around the cherry, filling the cup about a third of the way. The combination of cherry and pineapple will offer a delightful fruity base for the cupcakes.


Step 3: Mix the Cake Batter
In a large mixing bowl, combine the pineapple cake mix, 3 large eggs, 1 ½ cups of pineapple juice, and ½ cup of canola oil. Beat these ingredients together until the mixture is smooth and well-blended. The pineapple juice in the batter will enhance the pineapple flavor of the cupcakes.

Step 4: Fill the Muffin Cups and Bake
Carefully spoon the cake batter over the pineapple and cherry base in each muffin cup, filling them about two-thirds full. Place the muffin tin in the preheated oven and bake for 20-25 minutes. The cupcakes are done when they are golden brown and a toothpick inserted into the cake part comes out clean.

Step 5: Invert the Cupcakes
Once baked, remove the muffin tin from the oven and allow the cupcakes to cool for about 5 minutes. Then, carefully invert the muffin tin onto a baking sheet or a large platter. This step will reveal the beautiful pineapple and cherry topping on each cupcake.

Step 6: Garnish and Serve
Once the cupcakes are inverted and cool, dust them with powdered sugar for an added touch of sweetness and a visually appealing finish.


Cooking Note:

  • The key to perfect Pineapple Upside Down Cupcakes is the inversion process. It should be done swiftly and carefully to ensure the toppings stay intact and the cupcakes maintain their shape.

Serving Suggestions:

Serve these Pineapple Upside Down Cupcakes as a delightful dessert at your next gathering or as a special treat. They pair wonderfully with a cup of tea or coffee and are perfect for both casual and formal occasions.


  1. Butter and Sugar Layer: Ensure that the butter and brown sugar are evenly distributed in each muffin cup for a consistent caramelized base.
  2. Even Baking: Avoid overfilling the muffin cups with batter to ensure that the cupcakes bake evenly and don’t overflow.
  3. Cooling Time: Allow sufficient cooling time before inverting the cupcakes to prevent them from falling apart.

Prep Time:

  • Preparation Time: 15 minutes
  • Cooking Time: 25 minutes
  • Total Time: 40 minutes

Nutritional Information:

  • Calories: Approximately 200-250 per cupcake (varies based on the size and specific ingredients used)
  • Protein: 2-3g per cupcake
  • Sodium: Varies based on the cake mix and added ingredients


Pineapple Upside Down Cupcakes are a delightful and visually stunning dessert that offers all the flavors of a traditional pineapple upside-down cake but in a convenient and individually portioned form. These cupcakes are not only a treat for the palate but also for the eyes, making them a perfect choice for special occasions or as a delightful surprise for any dessert lover. Enjoy the harmonious blend of caramelized pineapple, cherry, and soft, moist cake in every bite!

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