Why You’ll Love This Recipe
- Individual Portions: Perfectly sized for single servings, making them ideal for parties and gatherings.
- Easy to Make: Utilizes a boxed cake mix for convenience without compromising on flavor.
- Visually Appealing: The caramelized pineapple and cherry topping creates a stunning presentation.
- Versatile: Great for desserts, snacks, or special occasions.
- Delicious Flavor: Combines the classic taste of pineapple upside-down cake in a fun, portable form.
Ingredients
(Tip: You'll find the full list of ingredients and measurements in the recipe card below.)
- Cooking spray
- ½ cup butter, melted
- 1½ cups brown sugar
- 24 maraschino cherries
- 1 (20-ounce) can crushed pineapple
- 1 (15.25-ounce) package pineapple cake mix (such as Duncan Hines Pineapple Supreme)
- 1⅓ cups pineapple juice
- ⅓ cup vegetable oil
- 3 large eggs
- 1 tablespoon confectioners' sugar for dusting (optional)
Directions
- Prepare the Oven and Pan: Preheat your oven to 350°F (175°C). Spray 24 muffin cups with cooking spray.
- Add Toppings: In each muffin cup, add 1 teaspoon of melted butter, followed by 1 tablespoon of brown sugar. Place a maraschino cherry in the center and spoon a heaping tablespoon of crushed pineapple over the cherry, pressing it down to create an even layer.
- Prepare the Batter: In a large bowl, combine the pineapple cake mix, pineapple juice, vegetable oil, and eggs. Beat with an electric mixer on low speed for about 30 seconds until moistened, then increase to medium speed and mix for 2 minutes until well combined.
- Fill the Cups: Pour the batter over the pineapple layer in each muffin cup, filling them to the top but avoiding overfilling.
- Bake: Bake in the preheated oven for approximately 20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
- Cool and Serve: Allow the cupcakes to cool in the pan for at least 5 minutes. Place a sheet of waxed paper on your work surface, then invert the muffin tin onto the paper, releasing the cupcakes. Serve with the pineapple and cherry side up. Dust with confectioners' sugar if desired.
Servings and Timing
- Servings: This recipe yields 24 cupcakes.
- Prep Time: 20 minutes
- Cook Time: 20 minutes
- Total Time: 45 minutes
Variations
- From Scratch: Replace the boxed cake mix with a homemade pineapple-flavored cake batter for a personal touch.
- Tropical Twist: Add shredded coconut or chopped nuts, such as pecans or macadamia nuts, to the topping mixture for added texture and flavor.
- Alternative Fruits: Substitute pineapple with other fruits like peaches or mangoes for a different flavor profile.
Storage/Reheating
- Storage: Store cooled cupcakes in an airtight container at room temperature for up to 2 days. For extended freshness, refrigerate for up to 5 days.
- Freezing: Wrap each cupcake individually in plastic wrap and place them in a freezer-safe bag. Freeze for up to 3 months. Thaw in the refrigerator overnight before serving.
- Reheating: To enjoy warm, microwave a cupcake for 10-15 seconds.
FAQs
Can I use a different type of cake mix?
Yes, a yellow or vanilla cake mix can be used if pineapple-flavored mix is unavailable.
Do I need to drain the crushed pineapple?
It's best to lightly drain the crushed pineapple to prevent excess moisture but retain some juice for flavor.
Can I make these cupcakes ahead of time?
Yes, they can be made a day in advance and stored in an airtight container.
What can I use instead of maraschino cherries?
Fresh or canned cherries, or even berries like raspberries, can be used as alternatives.
How do I prevent the topping from sticking to the pan?
Ensure the muffin cups are well-coated with cooking spray, and allow the cupcakes to cool for a few minutes before inverting.
Can I use fresh pineapple instead of canned?
Yes, finely chop fresh pineapple to use in place of canned crushed pineapple.
What if I don't have a muffin tin?
You can use silicone muffin cups placed on a baking sheet as an alternative.
How can I make the cupcakes less sweet?
Reduce the amount of brown sugar in the topping to lessen the sweetness.
Can I add rum for a tropical flavor?
A tablespoon of rum can be added to the batter for a subtle tropical taste.
Are these cupcakes suitable for freezing?
Yes, they freeze well when individually wrapped and stored properly.
Conclusion
Pineapple Upside-Down Cupcakes offer a delightful and convenient way to enjoy a classic dessert in individual portions.

Pineapple Upside-Down Cupcakes
- Total Time: 35 minutes
- Yield: 24 Servings
- Diet: Vegetarian
Description
Pineapple Upside-Down Cupcakes. These individual treats offer the delightful combination of caramelized pineapple and cherries atop a moist, flavorful cake. Perfect for gatherings or as a sweet indulgence, these cupcakes are both visually appealing and delicious.
Ingredients
-
Topping:
- ½ cup butter, melted
- 1½ cups brown sugar
- 24 maraschino cherries
- 1 (20-ounce) can crushed pineapple, drained
-
Cake Batter:
- 1 (15.25-ounce) package pineapple cake mix
- 1⅓ cups pineapple juice (reserved from the canned pineapple)
- ⅓ cup vegetable oil
- 3 large eggs
Instructions
-
Prepare the Oven and Pan:
- Preheat your oven to 350°F (175°C).
- Generously spray 24 muffin cups with cooking spray to prevent sticking.
-
Assemble the Topping:
- In each muffin cup, pour 1 teaspoon of melted butter.
- Add 1 tablespoon of brown sugar over the butter.
- Place a maraschino cherry in the center of each cup.
- Spoon a heaping tablespoon of drained crushed pineapple over the cherry, pressing it down gently to create an even layer.
-
Prepare the Cake Batter:
- In a large mixing bowl, combine the pineapple cake mix, reserved pineapple juice, vegetable oil, and eggs.
- Using an electric mixer, beat on low speed for about 30 seconds until moistened.
- Increase the speed to medium and continue beating for 2 minutes until the batter is smooth and well combined.
-
Fill the Muffin Cups:
- Pour the prepared batter over the pineapple mixture in each muffin cup, filling them to the top but avoiding overfilling.
-
Bake:
- Place the muffin tin in the preheated oven and bake for approximately 20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
-
Cool and Serve:
- Allow the cupcakes to cool in the pan for at least 5 minutes.
- Run a knife around the edges to loosen, then invert the muffin tin onto a waxed paper-lined surface, letting the cupcakes release with the pineapple side up.
- If desired, sprinkle lightly with confectioners' sugar before serving.
Notes
-
Variations:
- Pineapple Rings: For a traditional appearance, use pineapple rings instead of crushed pineapple, cutting them to fit the muffin cups if necessary.
- Nutty Addition: Sprinkle chopped pecans or walnuts over the brown sugar layer for added texture and flavor.
-
Storage:
- Store any leftover cupcakes in an airtight container at room temperature for up to 2 days.
- For extended freshness, refrigerate for up to 5 days.
-
Reheating:
- To enjoy warm, microwave individual cupcakes for about 10-15 seconds.
- Prep Time: 15 minutes
- Cook Time: 20 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American