Pineapple Upside-Down Cupcakes bring a delightful twist to the classic pineapple upside-down cake. Each cupcake is moist, sweet, and packed with tropical flavors. With pineapple chunks, a hint of cherry, and a soft vanilla cupcake base, these treats are perfect for any occasion. They’re easy to make and even easier to enjoy!

Why Make This Recipe
This recipe is great because it combines the nostalgia of pineapple upside-down cake with the convenience of cupcakes. They are perfect for parties, potlucks, or a simple family dessert. Plus, individual servings make them easy to serve and share. These cupcakes are sure to impress your friends and family with their vibrant colors and delicious flavors.
How to Make Pineapple Upside-Down Cupcakes
Making Pineapple Upside-Down Cupcakes is simple and fun! Follow the steps below, and you will have a delicious treat in no time.
Ingredients
- 6 tablespoons melted butter
- ¾ cup brown sugar
- 1 (20-ounce) can + 1 (8-ounce) can pineapple chunks in pineapple juice (or 28 ounces fresh chopped pineapple)
- 12 maraschino cherries
- 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
Directions
Toppings
- Preheat your oven to 350°F (175°C) and line a cupcake pan with cupcake liners.
- In a small bowl, melt the 6 tablespoons of butter and mix in the brown sugar. Divide this mixture evenly among the bottom of each cupcake liner.
- Place a few pineapple chunks and a maraschino cherry on top of the brown sugar mixture in each liner.
Cupcakes
- In a large mixing bowl, cream together the softened unsalted butter and granulated sugar until light and fluffy.
- Beat in the eggs, one at a time, and then add the vanilla extract.
- In another bowl, mix the all-purpose flour, baking powder, and salt.
- Gradually add the dry ingredients to the butter mixture, alternating with the buttermilk. Mix until just combined.
- Spoon the batter over the pineapple topping in each cupcake liner, filling about 2/3 full.
- Bake for 20-25 minutes or until a toothpick comes out clean from the center.
- Allow the cupcakes to cool for a few minutes, then carefully turn them upside down onto a serving platter.
How to Serve Pineapple Upside-Down Cupcakes
Serve your Pineapple Upside-Down Cupcakes warm or at room temperature. They make a great dessert on their own, but you can also top them with whipped cream or a scoop of vanilla ice cream for an extra treat.
How to Store Pineapple Upside-Down Cupcakes
Store any leftover cupcakes in an airtight container at room temperature for up to two days. If you need to keep them longer, they can be refrigerated for up to a week. Simply warm them up in the microwave for a few seconds before serving!
Tips to Make Pineapple Upside-Down Cupcakes
- Make sure your ingredients are at room temperature for the best mixing results.
- You can use fresh pineapple for a fresher taste if it’s available.
- Don’t overcrowd the cupcake liners; leave enough space for the cupcakes to rise.
Variation
Try adding shredded coconut or chopped nuts to the batter for an extra texture twist. You can also use different fruit such as peaches or cherries to create new flavors.
FAQs
1. Can I make these cupcakes ahead of time?
Yes, you can make the cupcakes a day in advance. Just store them in an airtight container once they’re cool.
2. Can I freeze Pineapple Upside-Down Cupcakes?
Yes, these cupcakes can be frozen. Place them in an airtight container or freezer bag and they can be stored in the freezer for up to three months.
3. What can I use instead of buttermilk?
If you don’t have buttermilk, you can use regular milk mixed with a tablespoon of vinegar or lemon juice. Let it sit for a few minutes before using.
Enjoy your delightful Pineapple Upside-Down Cupcakes, and have fun baking!

Pineapple Upside-Down Cupcakes
Ingredients
Toppings
- 6 tablespoons melted butter
- ¾ cup brown sugar
- 1 can 20-ounce can of pineapple chunks in pineapple juice (or fresh chopped pineapple)
- 12 pieces maraschino cherries
Cupcake Batter
- ½ cup softened unsalted butter Make sure it’s at room temperature.
- ¾ cup granulated sugar
- 2 pieces eggs
- 1 teaspoon vanilla extract
- 1 ½ cups all-purpose flour
- 1 ½ teaspoons baking powder
- ¼ teaspoon salt
- ½ cup buttermilk Can substitute with regular milk mixed with vinegar or lemon juice.
Instructions
Toppings
- Preheat your oven to 350°F (175°C) and line a cupcake pan with cupcake liners.
- In a small bowl, melt the 6 tablespoons of butter and mix in the brown sugar. Divide this mixture evenly among the bottom of each cupcake liner.
- Place a few pineapple chunks and a maraschino cherry on top of the brown sugar mixture in each liner.
Cupcake Batter
- In a large mixing bowl, cream together the softened unsalted butter and granulated sugar until light and fluffy.
- Beat in the eggs, one at a time, and then add the vanilla extract.
- In another bowl, mix the all-purpose flour, baking powder, and salt.
- Gradually add the dry ingredients to the butter mixture, alternating with the buttermilk. Mix until just combined.
- Spoon the batter over the pineapple topping in each cupcake liner, filling about 2/3 full.
- Bake for 20-25 minutes or until a toothpick comes out clean from the center.
- Allow the cupcakes to cool for a few minutes, then carefully turn them upside down onto a serving platter.


