Pineapple Upside-Down Cupcakes

Pineapple Upside-Down Cupcakes are a delightful twist on the classic dessert, offering the same sweet, tropical flavor in a perfectly portioned treat. Made entirely from scratch, these cupcakes are surprisingly easy to prepare and perfect for any occasion, from casual family gatherings to festive celebrations. Their caramelized pineapple topping and soft, buttery cake make them irresistible, and the addition of a maraschino cherry in the center adds a pop of color and sweetness.

Ingredients

Topping

• 6 tablespoons melted butter
• ¾ cup brown sugar
• 28 ounces pineapple chunks (from 20-ounce and 8-ounce cans in juice, or fresh chopped pineapple)
• 12 maraschino cherries

Cupcakes

• ½ cup softened unsalted butter
• ¾ cup granulated sugar
• 2 eggs
• 1 teaspoon vanilla extract
• 1 ½ cups all-purpose flour
• 1 ½ teaspoons baking powder
• ¼ teaspoon salt
• ½ cup buttermilk

Instructions

Topping

1. Preheat oven to 350°F and lightly spray a 12-count cupcake tin with non-stick baking spray.
2. Divide 6 tablespoons of melted butter evenly into the bottom of each cupcake well.
3. Sprinkle 1 tablespoon of brown sugar into each cupcake well over the butter.
4. Arrange 4 pineapple chunks in a flower pattern in each cup.
5. Press one maraschino cherry into the center of each pineapple “flower.” Set aside.

Cupcakes

1. In a medium bowl, cream ½ cup softened butter and ¾ cup granulated sugar until smooth using a hand mixer.
2. Add 2 eggs one at a time, mixing well after each addition.
3. Stir in 1 teaspoon vanilla extract.
4. In a separate bowl, whisk together 1 ½ cups all-purpose flour, 1 ½ teaspoons baking powder, and ¼ teaspoon salt.
5. Alternate adding the flour mixture and ½ cup buttermilk to the butter mixture, starting and ending with flour, mixing until just combined after each addition.
6. Spoon the batter evenly into the prepared cupcake tin, filling each well to the top.
7. Bake for 22-25 minutes until a toothpick inserted comes out clean.
8. Let cupcakes cool for 5 minutes. Cover the tin with a wire cooling rack, then carefully flip the tin to release the cupcakes.
9. Remove the tin and let cupcakes cool completely before serving.

Serving and Storage Tips

• Serve Pineapple Upside-Down Cupcakes slightly warm for the best flavor and texture.
• Pair them with a scoop of vanilla ice cream or a dollop of whipped cream for an extra indulgent treat.
• Store leftovers in an airtight container at room temperature for up to 2 days.
• Refrigerate for up to 5 days to keep them fresh longer.
• These cupcakes can also be frozen for up to 1 month. Thaw completely at room temperature before serving.
• Reheat briefly in the microwave or oven to enjoy them warm, just like freshly baked.

Variations

1. Tropical Coconut Twist
   Add ¼ cup shredded coconut to the cupcake batter for a tropical flavor that complements the pineapple topping. You can also sprinkle a little toasted coconut over the finished cupcakes for extra texture and aroma.
2. Mini Cupcake Version
   Use a mini cupcake tin to make bite-sized versions. Reduce baking time to 15-18 minutes. These are perfect for parties, potlucks, or kid-friendly treats.
3. Caramel Drizzle
   After flipping the cupcakes, drizzle caramel sauce over the pineapple topping for a richer, sweeter dessert. This adds a decadent touch ideal for special occasions.
4. Chocolate Pineapple
   Fold ¼ cup of white chocolate chips into the batter. The subtle sweetness of white chocolate pairs beautifully with the tangy pineapple, creating a unique flavor combination.
5. Fresh Fruit Variation
   Substitute pineapple chunks with other fruits like peaches, mango, or even a mix of berries. Adjust the sugar in the topping slightly if using naturally sweeter fruits.
6. Reduced Sugar Option
   Use ½ cup brown sugar for the topping and ½ cup granulated sugar in the batter to create a slightly less sweet version without compromising texture.
7. Gluten-Free Version
   Replace all-purpose flour with a gluten-free flour blend. Make sure the blend contains xanthan gum or another binding agent for the best texture.
8. Buttermilk-Free Option
   Substitute buttermilk with plain yogurt or milk mixed with 1 teaspoon of lemon juice. This still provides the moisture and tenderness without affecting the flavor.
9. Spiced Pineapple Cupcakes
   Add ½ teaspoon of ground cinnamon or nutmeg to the batter for a warm, spiced undertone that pairs nicely with the caramelized pineapple.
10. Maraschino Cherry-Free
    For a simpler version, omit the cherries and arrange pineapple chunks in a decorative pattern alone. This is great for those who prefer less sweetness or want a more natural fruit presentation.

FAQs

1. Can I use fresh pineapple instead of canned?
   Yes, fresh pineapple works well. Just make sure to drain excess juice to prevent soggy cupcakes.
2. How do I prevent the cupcakes from sticking to the pan?
   Lightly spray the cupcake tin with non-stick spray, and make sure to let the cupcakes cool slightly before flipping them onto the cooling rack.
3. Can I make these cupcakes ahead of time?
   Yes, you can prepare the topping and batter in advance and bake the cupcakes on the day you plan to serve them.
4. Can I use a different type of sugar?
   Brown sugar is recommended for the topping, but coconut sugar or raw sugar can be used as alternatives.
5. How should I store leftover cupcakes?
   Store in an airtight container at room temperature for up to 2 days or refrigerate for up to 5 days.
6. Can I freeze Pineapple Upside-Down Cupcakes?
   Yes, they freeze well for up to one month. Thaw completely before serving.
7. Can I make these gluten-free?
   Yes, replace the all-purpose flour with a gluten-free flour blend that contains a binding agent like xanthan gum.
8. Can I substitute buttermilk?
   Yes, use plain yogurt or milk mixed with 1 teaspoon of lemon juice as a buttermilk substitute.
9. Do I have to use maraschino cherries?
   No, they are optional. You can leave them out or use fresh cherries for a less sweet option.
10. Can I add other flavors to the cupcakes?
    Yes, you can add spices like cinnamon or nutmeg, fold in white chocolate chips, or sprinkle shredded coconut for added flavor.

Pineapple Upside-Down Cupcakes are a fun and delicious twist on the classic dessert, combining caramelized pineapple, sweet cherries, and a soft, buttery cake. They are simple to make from scratch and perfect for any occasion, from casual family treats to festive celebrations. With a variety of customization options and easy storage, these cupcakes are a versatile and crowd-pleasing dessert that everyone will love. Serve them warm for the best flavor and enjoy the tropical sweetness in every bite.

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