Pineapple Upside Down Cupcakes topped with cherries and pineapple slices

Pineapple Upside Down Cupcakes

Cooking method

  1. Preheat your oven to 350°F (175°C). Line a muffin tin with cupcake liners.
  2. In a small bowl, mix the melted butter and brown sugar until well combined. Pour a spoonful of the mixture into the bottom of each cupcake liner, then place a halved cherry on top.
  3. In a larger bowl, whisk together the flour, granulated sugar, baking powder, baking soda, and salt until evenly mixed.
  4. In another bowl, combine the milk, pineapple juice, applesauce, and vanilla extract. Mix well.
  5. Pour the wet ingredient mixture into the dry ingredients. Stir gently until just combined; don’t overmix!
  6. Carefully spoon the batter over the cherry and brown sugar mixture in each liner, filling them about two-thirds full.
  7. Bake for 20-25 minutes or until a toothpick inserted comes out clean.
  8. Let the cupcakes cool for about 5 minutes before flipping them onto a serving platter.

Best ways to enjoy it

Serving these Pineapple Upside Down Cupcakes is a joy in itself! For a tropical flair, consider dusting them with powdered sugar or drizzling with a simple glaze made from powdered sugar and pineapple juice. Pair them with a scoop of vanilla ice cream for a delectable dessert experience. You can also serve them alongside a tropical fruit salad to enhance the flavors of the pineapple.

Keeping leftovers fresh

If you have any cupcakes left over (though I doubt it!), keep them in an airtight container at room temperature for up to three days. You can also refrigerate them for longer freshness, but ensure they are well covered. If you want to store them for an extended period, consider freezing them. Wrap each cupcake tightly in plastic wrap and place them in a freezer-safe container—perfect for when a sweet craving hits!

Pro chef tips

To take your Pineapple Upside Down Cupcakes to the next level, here are some insider tips:

  • Use fresh pineapple instead of canned for a bright, refreshing taste.
  • For an added layer of flavor, sprinkle some shredded coconut over the pineapple before adding the batter.
  • Don’t rush the cooling process! Allow them to cool slightly before flipping, ensuring they keep their shape.

Creative twists

Feeling adventurous? Here are some ideas to mix things up:

  • Replace maraschino cherries with fresh berries for a summer twist.
  • Swap out regular flour for a gluten-free alternative, ensuring you get the right blend to maintain texture.
  • Add spices like cinnamon or nutmeg to the batter for a warm, aromatic touch.

Common questions

What is the prep time for these cupcakes?

Preparation takes about 15 minutes, and they bake in around 20-25 minutes. Overall, you can have these delicious cupcakes ready in under an hour!

Can I use other fruits for this recipe?

Absolutely! While traditional recipes feature pineapple, you can experiment with peaches, cherries, or apples. Adjust cooking time based on the fruit tenderness.

How should I safely store leftovers?

Store leftover cupcakes in an airtight container at room temperature for up to 3 days. For longer storage, freeze individually wrapped cupcakes for up to 2 months—just thaw when you’re ready to indulge!

With these enticing Pineapple Upside Down Cupcakes, you’ll find yourself transported to a tropical paradise with every bite. Happy baking!

Pineapple Upside Down Cupcakes

Delightful individual-sized treats that combine fluffy vanilla cake with the tropical sweetness of pineapple and a gooey cherry surprise.
Prep Time 15 minutes
Cook Time 25 minutes
Total Time 40 minutes
Servings: 12 cupcakes
Course: Dessert
Cuisine: American, Tropical
Calories: 200

Ingredients
  

Base Layer
  • 1/4 cup unsalted butter, melted
  • 1/2 cup brown sugar, packed
  • 12 pieces maraschino cherries, halved
Cupcake Batter
  • 1 cup all-purpose flour
  • 1/2 cup granulated sugar
  • 1/2 cup milk For dairy-free, substitute with almond or oat milk.
  • 1/4 cup pineapple juice
  • 1/4 cup unsweetened applesauce
  • 1 teaspoon baking powder
  • 1/2 teaspoon vanilla extract
  • 1/4 teaspoon salt
  • 1/2 teaspoon baking soda

Method
 

Preparation and Baking
  1. Preheat your oven to 350°F (175°C). Line a muffin tin with cupcake liners.
  2. In a small bowl, mix the melted butter and brown sugar until well combined. Pour a spoonful of the mixture into the bottom of each cupcake liner, then place a halved cherry on top.
  3. In a larger bowl, whisk together the flour, granulated sugar, baking powder, baking soda, and salt until evenly mixed.
  4. In another bowl, combine the milk, pineapple juice, applesauce, and vanilla extract. Mix well.
  5. Pour the wet ingredient mixture into the dry ingredients. Stir gently until just combined; don't overmix!
  6. Carefully spoon the batter over the cherry and brown sugar mixture in each liner, filling them about two-thirds full.
  7. Bake for 20-25 minutes or until a toothpick inserted comes out clean.
  8. Let the cupcakes cool for about 5 minutes before flipping them onto a serving platter.

Notes

To enhance flavors, consider dusting with powdered sugar or drizzling with a glaze made from powdered sugar and pineapple juice. Pair with vanilla ice cream or a tropical fruit salad.

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