Why You’ll Love This Recipe

These cupcakes offer the perfect balance of sweet, tangy pineapple and rich caramelized brown sugar in every bite. They are easy to make using a boxed cake mix, but you can also adapt the recipe to make it from scratch. The maraschino cherry in the center adds a pop of color and flavor, making these cupcakes as beautiful as they are delicious.

Ingredients

Cooking spray
½ cup butter, melted
1 ½ cups brown sugar
24 maraschino cherries
1 (20-ounce) can crushed pineapple, drained
1 (15.25-ounce) package pineapple cake mix (such as Duncan Hines Pineapple Supreme)
1 ⅓ cups pineapple juice (from the canned pineapple)
⅓ cup vegetable oil
3 large eggs
1 tablespoon confectioners’ sugar for dusting (optional)

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

Directions

Preheat the Oven: Set your oven to 350°F (175°C). Move an oven rack to the middle position. Spray 24 muffin cups with cooking spray.
Prepare the Topping: Spoon 1 teaspoon of melted butter into each muffin cup. Add 1 tablespoon of brown sugar and press a maraschino cherry into the center. Spoon a heaping tablespoon of crushed pineapple over the brown sugar and press it into an even layer.
Prepare the Cake Batter: In a large bowl, mix the pineapple cake mix, pineapple juice, vegetable oil, and eggs using an electric mixer. Start on low speed until moistened (about 30 seconds), then increase to medium speed and mix for 2 minutes.
Fill the Muffin Cups: Pour the cake batter into the muffin cups, filling them to the top but not overfilling.
Bake: Place in the preheated oven and bake for about 20 minutes, or until a toothpick inserted into the center comes out clean.
Cool and Invert: Let the cupcakes cool for at least 5 minutes. Line a work surface with waxed paper, then carefully invert the cupcakes onto the paper so the pineapple and cherry topping is on top.
Serve: Sprinkle lightly with confectioners’ sugar before serving, if desired.

Servings and Timing

Servings: 24 cupcakes
Prep Time: 20 minutes
Cook Time: 20 minutes
Additional Time: 5 minutes
Total Time: 45 minutes

Variations

From Scratch: Swap the boxed cake mix for a homemade vanilla or pineapple cake batter.
Extra Caramel Flavor: Add a pinch of cinnamon or nutmeg to the brown sugar mixture.
Nutty Crunch: Sprinkle chopped pecans or walnuts over the brown sugar layer before adding the pineapple.
Dairy-Free Option: Use melted coconut oil instead of butter and a dairy-free cake mix.

Storage/Reheating

Store leftover cupcakes in an airtight container at room temperature for up to 2 days or in the refrigerator for up to 5 days.
Reheat in the microwave for 10-15 seconds to refresh the caramelized topping.
These cupcakes can also be frozen for up to 2 months. Wrap individually in plastic wrap and store in a freezer-safe bag.

FAQs

Can I use fresh pineapple instead of canned?

Yes! Just finely chop fresh pineapple and use pineapple juice or another liquid substitute for the batter.

Can I make these cupcakes ahead of time?

Yes! Bake them a day ahead and store them in an airtight container. Reheat slightly before serving for a fresh taste.

How do I prevent the cupcakes from sticking?

Make sure to grease the muffin tin well, and allow the cupcakes to cool slightly before inverting them. Running a knife around the edges can also help release them.

Can I use a different cake mix?

Yes, a yellow or vanilla cake mix works well if you can’t find a pineapple-flavored mix.

How do I keep the topping from getting too soggy?

Drain the crushed pineapple well before adding it to the muffin tin.

Can I add coconut?

Yes! Add shredded coconut to the brown sugar mixture for a tropical twist.

Do I need cupcake liners?

No, these are baked directly in a greased muffin tin since they need to be inverted after baking.

Can I make mini cupcakes instead?

Yes! Use a mini muffin tin and adjust the baking time to about 12-15 minutes.

How do I make the cupcakes extra moist?

Using an extra egg or a splash of sour cream in the batter can help create an ultra-moist texture.

Can I make this as a full cake instead?

Yes! Use a round or square cake pan and adjust the baking time to 30-40 minutes.

Conclusion

Pineapple Upside-Down Cupcakes are a fun, easy, and delicious twist on a classic dessert. They’re sweet, moist, and packed with tropical flavors that make them perfect for any occasion. Whether you serve them at a party or just as a treat for yourself, these cupcakes are sure to be a hit!

Pineapple Upside-Down Cupcakes

Print Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star

No reviews

Pineapple Upside-Down Cupcakes are a fun and easy twist on the classic cake, featuring caramelized brown sugar, tangy pineapple, and a moist cake base. These individual-sized treats are perfect for parties, brunches, or any occasion where you want a tropical-flavored dessert. Made with a simple boxed cake mix or homemade batter, these cupcakes are both delicious and visually stunning!

Author: Amy
Prep Time: 20 minutes
Cook Time: 20 minutes
Total Time: 45 minutes
Yield: 24 cupcakes
Category: Dessert, Cupcakes
Method: Baking
Cuisine: American
Diet: Vegetarian

Instructions

Preheat the Oven:
- Set oven to 350°F (175°C). Move an oven rack to the middle position.
- Spray 24 muffin cups with cooking spray.
Prepare the Topping:
- Spoon 1 teaspoon of melted butter into each muffin cup.
- Add 1 tablespoon of brown sugar and press a maraschino cherry into the center.
- Spoon a heaping tablespoon of crushed pineapple over the brown sugar, pressing it into an even layer.
Prepare the Cake Batter:
- In a large bowl, mix the pineapple cake mix, pineapple juice, vegetable oil, and eggs using an electric mixer.
- Start on low speed until moistened (about 30 seconds), then increase to medium speed and mix for 2 minutes.
Fill the Muffin Cups:
- Pour the cake batter into the muffin cups, filling them to the top but not overfilling.
Bake:
- Place in the preheated oven and bake for about 20 minutes, or until a toothpick inserted into the center comes out clean.
Cool and Invert:
- Let the cupcakes cool for at least 5 minutes.
- Line a work surface with waxed paper, then carefully invert the cupcakes onto the paper so the pineapple and cherry topping is on top.
Serve:
- Sprinkle lightly with confectioners’ sugar before serving, if desired.

Notes

Variations:
- Use a homemade vanilla or pineapple cake batter instead of a boxed mix.
- Add a pinch of cinnamon or nutmeg to the brown sugar for extra caramel flavor.
- Sprinkle chopped pecans or walnuts over the brown sugar layer for added crunch.
- Make dairy-free by using melted coconut oil instead of butter and a dairy-free cake mix.
Storage & Reheating:
- Store in an airtight container at room temperature for up to 2 days or in the refrigerator for up to 5 days.
- Reheat in the microwave for 10-15 seconds to refresh the caramelized topping.
- Freeze cupcakes without toppings for up to 2 months. Wrap individually and store in a freezer-safe bag.