Pineapple Upside Down Cupcakes topped with pineapple slices and cherries

Pineapple Upside Down Cupcakes

Step-by-Step Instructions

  1. Preheat your oven to 350°F (175°C) and line a cupcake pan with liners.
  2. Combine melted butter and brown sugar in a small bowl. Mix until smooth. Spoon this mixture into the bottom of each cupcake liner.
  3. Place two pieces of pineapple and half a cherry on top of the butter-sugar mixture in each liner.
  4. In another bowl, whisk together flour, baking powder, baking soda, and salt.
  5. In a separate bowl, combine granulated sugar, milk, vanilla extract, and egg. Whisk until blended.
  6. Gradually add the dry ingredients to the wet ingredients, mixing just until combined.
  7. Pour the batter over the topping in each liner, filling them about 2/3 full.
  8. Bake for 18-20 minutes, or until a toothpick inserted into the center comes out clean.
  9. Allow to cool for a few minutes before inverting onto a plate. Serve warm while the flavors are still vibrant.

Best Ways to Enjoy It

These Pineapple Upside Down Cupcakes are best enjoyed warm, showcasing their gooey centers and caramelized tops. For an extra touch, consider dusting the cupcakes with a bit of powdered sugar. They pair beautifully with a scoop of vanilla ice cream or a dollop of whipped cream, adding creaminess to the sweet flavors. You might also serve them alongside fresh tropical fruit salad for a refreshing contrast or brew a robust coffee to enhance the dessert experience.

How to Store & Freeze

To keep your Pineapple Upside Down Cupcakes fresh, store them in an airtight container at room temperature for up to three days. If you’d like to save them for later, you can freeze these cupcakes. Just wrap each cupcake tightly in plastic wrap and place them in a freezer-safe container. They can be stored in the freezer for up to three months. To enjoy, simply thaw at room temperature and reheat briefly in the oven.

Helpful Cooking Tips

  • Don’t skip the lining: Properly lining the cupcake pan ensures easy removal and prevents the caramel from sticking.
  • Keep the pineapple chunks dry: If using canned pineapple, make sure to drain it well to avoid soggy cupcakes.
  • Mix gently: Overmixing can lead to dense cupcakes; mix until just combined for the best texture.

Creative Twists

Feel free to experiment with variations of this recipe! You can add shredded coconut for a tropical twist or swap the cherries for fresh blueberries or strawberries for a berry burst. Looking for something healthier? Substitute part of the granulated sugar with applesauce or mashed bananas—the cupcakes will still turn out moist and delicious!

FAQs

How long do Pineapple Upside Down Cupcakes take to prepare?

The prep time is around 15 minutes, and then they’ll bake for 18-20 minutes, making them a quick dessert option.

Can I use fresh pineapple instead of canned?

Absolutely! Just make sure to cut it into small, even pieces and drain any excess juice to avoid a soggy bottom.

How do I know when they’re done baking?

Insert a toothpick into the center of a cupcake; if it comes out clean or with just a few crumbs, they’re ready to go!

With these handy tips and insights, you’re all set to make your very own Pineapple Upside Down Cupcakes—a delightful treat for any occasion!

Pineapple Upside Down Cupcakes

Delightful mini cupcakes featuring caramelized pineapple and cherries atop a fluffy cake, perfect for any occasion.
Prep Time 15 minutes
Cook Time 20 minutes
Total Time 35 minutes
Servings: 12 cupcakes
Course: Dessert, Snack
Cuisine: American
Calories: 200

Ingredients
  

Topping
  • 1/4 cup unsalted butter, melted Use unsalted for better flavor control
  • 1/2 cup brown sugar, packed For a richer flavor, use dark brown sugar
  • 12 pieces maraschino cherries, halved Place on top of pineapple
  • 1 cup pineapple chunks (or crushed pineapple, drained) Choose based on preference
Cupcake Batter
  • 1 cup all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/4 cup granulated sugar
  • 1/4 cup milk
  • 1 teaspoon vanilla extract
  • 1 large egg

Method
 

Preparation
  1. Preheat your oven to 350°F (175°C) and line a cupcake pan with liners.
  2. Combine melted butter and brown sugar in a small bowl. Mix until smooth. Spoon this mixture into the bottom of each cupcake liner.
  3. Place two pieces of pineapple and half a cherry on top of the butter-sugar mixture in each liner.
  4. In another bowl, whisk together flour, baking powder, baking soda, and salt.
  5. In a separate bowl, combine granulated sugar, milk, vanilla extract, and egg. Whisk until blended.
  6. Gradually add the dry ingredients to the wet ingredients, mixing just until combined.
  7. Pour the batter over the topping in each liner, filling them about 2/3 full.
Baking
  1. Bake for 18-20 minutes, or until a toothpick inserted into the center comes out clean.
  2. Allow to cool for a few minutes before inverting onto a plate. Serve warm.

Notes

These cupcakes are best enjoyed warm, and they can be served with powdered sugar, vanilla ice cream, or whipped cream. Store in an airtight container for up to three days or freeze for later use.

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