Dive into the delightful world of Pineapple Upside-Down Cupcakes, a charming twist on the classic dessert that's sure to bring a touch of nostalgia with every bite. These individual servings feature the traditional caramelized pineapple and cherry topping, baked directly into moist and fluffy cupcakes. Perfect for parties, family gatherings, or as a special treat to brighten your day, these cupcakes are as fun to make as they are to eat.

Whether you’re an experienced baker or trying this for the first time, this recipe will guide you through creating a dessert that’s not only delicious but also visually appealing with its vibrant fruit topping. Let’s start baking these irresistible treats!
Sweet and Simple: Baking Made Fun
Pineapple Upside-Down Cupcakes offer a perfect balance of sweetness and texture. Here are some tips to ensure they come out perfectly.
Pro Tips for Perfect Pineapple Upside-Down Cupcakes:
- Even Toppings: Start with a consistent layer of butter and sugar in each muffin cup to ensure each cupcake caramelizes beautifully.
- Fruit Placement: Arrange the cherry and pineapple pieces neatly at the bottom for a visually appealing result once inverted.
- Batter Consistency: Follow the cake mix instructions closely for the best texture, substituting pineapple juice for water to enhance the pineapple flavor throughout the cake.
- Check Doneness: Insert a toothpick into the center of a cupcake to check for doneness it should come out clean.
- Cool Before Inverting: Let the cupcakes cool for a few minutes in the pan before inverting to prevent them from falling apart.
Pineapple Upside-Down Cupcakes Recipe:
- Preparation time: 15 minutes
- Cooking time: 25 minutes
- Servings: 12 cupcakes
- Equipment: 12-cup muffin tin
This recipe is perfect for any occasion or as a delightful everyday dessert.
Ingredients:
- ¼ cup butter, melted
- ½ cup brown sugar, packed
- 24 maraschino cherries
- 1 can (20 oz) pineapple rings, drained and juice reserved
- 1 box yellow cake mix
- Additional ingredients called for on cake mix box (typically water, oil, and eggs)
Directions:
- Prepare the Oven and Pan: Heat your oven to 350°F (175°C). Grease a 12-cup muffin tin with butter or cooking spray.
- Prepare the Fruit: Cut pineapple rings into quarters to fit into the muffin cups.
- Assemble the Toppings: In each muffin cup, place 1 teaspoon of melted butter and 1 teaspoon of brown sugar. Add a cherry to the center and arrange two pineapple quarters around it.
- Mix the Batter: Prepare the cake mix according to the package directions, substituting some of the water with pineapple juice for enhanced flavor.
- Fill the Cups: Spoon the batter over the pineapple and cherries, filling each cup about ¾ full.
- Bake: Place in the oven and bake for 20-25 minutes, until a toothpick inserted into the center comes out clean.
- Cool and Invert: Let the cupcakes cool in the pan for 5 minutes, then invert onto a wire rack to cool completely. This allows the caramelized sugar to drizzle over the cupcakes.
Ready to Enjoy!
Your Pineapple Upside-Down Cupcakes are now ready to be served. Enjoy the sweet pineapple and cherry flavors combined with the soft, moist texture of the cake. These cupcakes make a delightful treat for any dessert lover, combining classic flavors with a fun, individual twist!
Print📖 Recipe
Pineapple Upside-Down Cupcakes
This recipe is perfect for any occasion or as a delightful everyday dessert.
- Total Time: 40 minutes
- Yield: 12 cupcakes 1x
Ingredients
- ¼ cup butter, melted
- ½ cup brown sugar, packed
- 24 maraschino cherries
- 1 can (20 oz) pineapple rings, drained and juice reserved
- 1 box yellow cake mix
- Additional ingredients called for on cake mix box (typically water, oil, and eggs)
Instructions
- Prepare the Oven and Pan: Heat your oven to 350°F (175°C). Grease a 12-cup muffin tin with butter or cooking spray.
- Prepare the Fruit: Cut pineapple rings into quarters to fit into the muffin cups.
- Assemble the Toppings: In each muffin cup, place 1 teaspoon of melted butter and 1 teaspoon of brown sugar. Add a cherry to the center and arrange two pineapple quarters around it.
- Mix the Batter: Prepare the cake mix according to the package directions, substituting some of the water with pineapple juice for enhanced flavor.
- Fill the Cups: Spoon the batter over the pineapple and cherries, filling each cup about ¾ full.
- Bake: Place in the oven and bake for 20-25 minutes, until a toothpick inserted into the center comes out clean.
- Cool and Invert: Let the cupcakes cool in the pan for 5 minutes, then invert onto a wire rack to cool completely. This allows the caramelized sugar to drizzle over the cupcakes.
- Prep Time: 15 minutes
- Cook Time: 25 minutes
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