Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, offering soft, moist cupcakes topped with tender pineapple pieces and a cherry on top. This easy recipe yields 21 delicious cupcakes that combine the sweet caramel flavor of brown sugar and butter with juicy pineapple and maraschino cherries, making them perfect for any occasion.

Ingredients

• ½ cup butter, melted
• ½ cup brown sugar, packed
• 1 can (20 ounces) pineapple slices or chunks with juice, divided
• 21 maraschino cherries, stemless
• 2 cups all-purpose flour
• 2 teaspoons baking powder
• ½ teaspoon salt
• ½ teaspoon baking soda
• ¼ cup canola oil
• ¾ cup granulated sugar
• 2 large eggs, room temperature

Instructions

1. Preheat the oven to 350°F.
2. Divide the pineapple and juice from the can. Cut the pineapple into small pieces about ½ inch square.
3. Spoon 1 teaspoon of melted butter into each muffin cup.
4. Sprinkle about 1 teaspoon of brown sugar evenly over the butter in each cup.
5. Arrange 4 pieces of pineapple in a flower or cross shape inside each muffin cup.
6. Place one maraschino cherry in the center of the pineapple pieces in each cup. Set the pan aside.
7. In a small bowl, whisk together the flour, baking powder, salt, and baking soda.
8. In a large bowl, whisk the canola oil and granulated sugar until combined.
9. Beat in the eggs until just mixed.
10. Gradually fold the dry ingredients into the wet ingredients using a spatula.
11. When the batter begins to thicken and dry, pour in the reserved pineapple juice and mix until the batter is wet and thick.
12. Spoon about 2 tablespoons of batter over the pineapple and cherry in each muffin cup, filling almost to the top.
13. Bake the cupcakes for 15 to 17 minutes or until the edges are golden brown and a toothpick inserted in the center comes out clean.
14. Let the cupcakes cool in the pan for 30 minutes.
15. Run a thin knife around the edges of each cupcake to loosen them from the pan.
16. Carefully invert each cupcake onto a cooling rack so the pineapple and cherry are on top.

Serving and Storage Tips

Serve Pineapple Upside Down Cupcakes slightly warm or at room temperature for the best flavor and texture. They pair well with a scoop of vanilla ice cream or a dollop of whipped cream for an extra special treat.

To store, keep the cupcakes in an airtight container at room temperature for up to 2 days. For longer storage, refrigerate them for up to 5 days. Before serving refrigerated cupcakes, allow them to come to room temperature or warm them briefly in the microwave.

You can also freeze these cupcakes by wrapping each one individually in plastic wrap and placing them in a freezer-safe container. Freeze for up to one month. When ready to eat, thaw overnight in the refrigerator and warm slightly before serving for optimal taste and texture.

Variations

1. Coconut Pineapple Upside Down Cupcakes
   Add ½ cup shredded sweetened coconut to the cupcake batter for a tropical twist. Sprinkle some extra coconut on top of the pineapple pieces before baking to add texture and flavor. The coconut pairs beautifully with the pineapple for a more island-inspired dessert.
2. Spiced Pineapple Upside Down Cupcakes
   Enhance the batter by adding 1 teaspoon ground cinnamon and ¼ teaspoon ground nutmeg to the dry ingredients. These warm spices complement the sweetness of the pineapple and brown sugar, giving the cupcakes a cozy, spiced flavor perfect for cooler months.
3. Pineapple Upside Down Cupcakes with Rum Glaze
   After baking, brush the tops of the inverted cupcakes with a simple glaze made from 2 tablespoons rum mixed with ¼ cup powdered sugar. This adds a subtle boozy note that balances the sweetness and makes the cupcakes more decadent.
4. Mini Pineapple Upside Down Cupcakes
   Use mini muffin pans to make bite-sized versions of these cupcakes. Adjust baking time to about 10-12 minutes. These are great for parties or as finger food desserts.
5. Vegan Pineapple Upside Down Cupcakes
   Substitute the butter with vegan margarine or coconut oil, replace eggs with flax eggs (1 tablespoon ground flaxseed mixed with 3 tablespoons water per egg), and use plant-based milk instead of any dairy if needed. These modifications keep the cupcakes moist and delicious without animal products.
6. Gluten-Free Pineapple Upside Down Cupcakes
   Replace all-purpose flour with a gluten-free flour blend that includes xanthan gum. Ensure baking powder is gluten-free. This variation makes the cupcakes suitable for those with gluten intolerance while maintaining a tender crumb.
7. Caramel Drizzled Pineapple Upside Down Cupcakes
   After cooling, drizzle warm caramel sauce over the top of the cupcakes for an extra layer of sweetness and richness. The caramel complements the brown sugar and pineapple perfectly.
8. Pineapple Upside Down Cupcakes with Cream Cheese Frosting
   Top the cooled cupcakes with a dollop of cream cheese frosting for a tangy contrast to the sweet pineapple topping. This turns the cupcakes into a more indulgent dessert option.

Each of these variations allows you to customize the classic Pineapple Upside Down Cupcakes to suit different tastes and occasions, making this recipe even more versatile and fun to bake.

FAQs

1. Can I use fresh pineapple instead of canned?
   Yes, you can use fresh pineapple. Just cut it into small ½-inch pieces and use some fresh pineapple juice or a little water to replace the canned juice in the batter.
2. What type of cherries should I use?
   Maraschino cherries work best because they are sweet and have a vibrant color that complements the cupcakes. Make sure to use stemless cherries for easier placement.
3. Can I make this recipe dairy-free?
   Yes, substitute the butter with dairy-free margarine or coconut oil. The rest of the recipe can remain the same.
4. How do I store leftover cupcakes?
   Store cupcakes in an airtight container at room temperature for up to 2 days or refrigerate for up to 5 days. For longer storage, freeze them individually wrapped.
5. Can I prepare these cupcakes ahead of time?
   Yes, you can assemble the cupcakes and refrigerate the batter in the muffin pans overnight. Bake them the next day, but add a couple of extra minutes to the baking time.
6. How do I prevent the pineapple and sugar from sticking to the pan?
   Make sure to grease the muffin pans well with melted butter and sprinkle the brown sugar evenly. This creates a caramelized layer that helps the pineapple pieces release easily when inverted.
7. What can I use if I don’t have canola oil?
   You can substitute canola oil with vegetable oil, melted coconut oil, or even light olive oil.
8. Why do the cupcakes sometimes come out soggy?
   Overcrowding the pan or baking at a too-low temperature can cause sogginess. Also, be careful not to add too much pineapple juice to the batter.
9. Can I double the recipe?
   Yes, you can double the ingredients and bake in batches or use additional muffin pans. Adjust baking time slightly if needed.
10. Are these cupcakes suitable for freezing?
    Yes, they freeze well. Wrap each cupcake tightly in plastic wrap and place them in a freezer-safe container for up to one month. Thaw in the refrigerator before serving.

This Pineapple Upside Down Cupcakes recipe is an easy, crowd-pleasing dessert that combines classic flavors in a convenient cupcake form. With tender pineapple pieces and a bright cherry on top, these cupcakes are perfect for parties, potlucks, or anytime you want a sweet tropical treat. Enjoy the moist texture and rich caramel notes in every bite.

Print