Why You’ll Love This Recipe

Pineapple Upside Down Cupcakes are an easy, individual version of the traditional upside-down cake that’s both nostalgic and indulgent. With a perfectly caramelized pineapple topping and a light, fluffy cake base, these cupcakes offer a delightful balance of sweet and tangy flavors. Whether you’re a fan of pineapple desserts or just love a new spin on a classic, these cupcakes will quickly become a favorite. They’re easy to serve, making them a great option for entertaining or as a homemade treat when you want to impress without spending too much time in the kitchen.

Ingredients

1 can (20 oz) pineapple rings, drained (reserve juice)
1/2 cup (1 stick) unsalted butter, melted
1/2 cup packed brown sugar
12 maraschino cherries
1 1/2 cups all-purpose flour
1 cup granulated sugar
2 teaspoons baking powder
1/4 teaspoon salt
1/2 cup whole milk
1/4 cup pineapple juice (from the can of pineapple)
1 teaspoon vanilla extract
2 large eggs
1/4 cup vegetable oil

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

Directions

Preheat your oven to 350°F (175°C). Line a 12-cup muffin tin with cupcake liners or grease the muffin cups with non-stick spray.
In a small bowl, combine the melted butter and brown sugar. Spoon about 1 tablespoon of the mixture into the bottom of each muffin cup.
Place one pineapple ring in each muffin cup, pressing it gently into the butter-sugar mixture. Place a maraschino cherry in the center of each pineapple ring.
In a medium bowl, whisk together the flour, sugar, baking powder, and salt.
In another bowl, combine the milk, pineapple juice, vanilla extract, eggs, and vegetable oil. Whisk until smooth.
Add the wet ingredients to the dry ingredients and stir until just combined. Be careful not to overmix.
Divide the batter evenly among the muffin cups, filling each about 2/3 of the way full. Make sure the batter covers the pineapple and cherry topping.
Bake for 18-22 minutes, or until a toothpick inserted into the center comes out clean.
Let the cupcakes cool in the pan for 5 minutes, then carefully invert the muffin tin onto a cooling rack or a tray. Allow the cupcakes to cool completely before serving.

Servings and timing

Servings: 12
Total Time: 40-45 minutes (includes baking time)

Variations

Add coconut: Sprinkle shredded coconut on top of the pineapple before baking for a tropical twist.
Use fresh pineapple: If you prefer fresh fruit, substitute the canned pineapple rings with fresh pineapple slices for a more vibrant, natural flavor.
Spices: Add a dash of cinnamon or nutmeg to the batter for a warm, cozy flavor that pairs beautifully with pineapple.
Vegan option: Use a flax egg or chia egg, and substitute the butter with vegan margarine or coconut oil to make these cupcakes vegan-friendly.

Storage/Reheating

Storage: Store any leftover cupcakes in an airtight container at room temperature for up to 2 days. You can also refrigerate them for up to 5 days.
Reheating: To reheat, simply place the cupcakes in the microwave for about 10-15 seconds, or warm them up in the oven at 350°F for 5-7 minutes.

FAQs

1. Can I use fresh pineapple instead of canned pineapple?

Yes, fresh pineapple works just as well! Just make sure to slice it into rings and remove the core before using it in place of canned pineapple rings.

2. Can I make these cupcakes ahead of time?

Yes, you can make these cupcakes ahead of time. They store well in an airtight container and can be refrigerated for up to 5 days. You can also freeze them for longer storage.

3. Can I substitute the maraschino cherries with something else?

If you don’t like maraschino cherries, you can substitute them with fresh cherries or even berries, although the texture and presentation might vary.

4. Can I make a larger version of this recipe in a regular cake pan?

Yes, you can make a single large pineapple upside down cake by doubling the recipe and baking it in a 9-inch round or square cake pan. Just bake it for about 35-40 minutes, or until a toothpick comes out clean.

5. Can I use a gluten-free flour blend for this recipe?

Yes, you can use a gluten-free flour blend in place of all-purpose flour. Just ensure your baking powder and other ingredients are also gluten-free.

6. Can I add nuts to the topping?

Yes, you can sprinkle chopped pecans or walnuts over the pineapple and cherry topping before baking for added crunch and flavor.

7. Can I make these cupcakes without eggs?

Yes, you can substitute eggs with a flax egg (1 tablespoon ground flaxseed mixed with 3 tablespoons water) or another egg replacer of your choice.

8. Can I use cake mix instead of making the batter from scratch?

Yes, you can substitute the homemade batter with a yellow cake mix for an even quicker version. Just follow the instructions on the cake mix box, adding the pineapple juice to the wet ingredients for extra flavor.

9. Can I use a different fruit besides pineapple?

While pineapple is traditional for this recipe, you can try using peaches, apricots, or even pears for a similar upside-down effect.

10. How do I prevent the cupcakes from sticking to the pan?

To prevent sticking, be sure to grease the muffin tin well, or use cupcake liners. Additionally, inverting the pan while the cupcakes are still warm helps release them more easily.

Conclusion

Pineapple Upside Down Cupcakes are a charming and delicious twist on the classic dessert, offering the same beloved flavors in individual portions. With caramelized pineapple, a rich buttery cake, and the bright addition of maraschino cherries, these cupcakes are perfect for any occasion. Whether you’re hosting a party, celebrating a special moment, or just craving something sweet, these cupcakes bring a tropical flair to your dessert table with minimal effort. Enjoy the nostalgic flavors of pineapple upside-down cake in a fun and easy-to-eat form!