Why You’ll Love This Recipe
This Pineapple Upside Down Cupcakes recipe works wonders because it combines the tanginess of pineapple with the sweetness of brown sugar and the lightness of vanilla cake. The buttery caramelized topping adds a rich, gooey texture that complements the moist and fluffy interior of the cupcake. The easy-to-follow process, with simple ingredients like canned pineapple rings and maraschino cherries, makes this recipe both quick and delicious.
Additionally, the individual serving size of the cupcakes allows for perfect presentation, making them ideal for any occasion. The best part? The simple invert and serve method ensures that the pineapple topping stays beautifully intact, showcasing its stunning golden-brown color. You’ll find that once you try this recipe, it will quickly become a favorite for both your family and guests.
Ingredients
This sweet treat requires a handful of basic ingredients you likely already have in your pantry:
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1/4 cup unsalted butter, melted
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1/2 cup light brown sugar
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4-5 slices canned pineapple rings
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1/3 cup pineapple juice
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1 cup all-purpose flour
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3/4 cup granulated sugar
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1/4 cup vegetable oil
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1 large egg
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1 tsp baking powder
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1/2 tsp salt
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1/2 cup milk
(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)
Directions
Follow these simple steps to create these individual upside-down cakes:
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Make the Pineapple Topping
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Preheat the oven to 350°F (175°C).
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In a bowl, combine melted butter and brown sugar, then divide the mixture evenly into the cups of a muffin tin.
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Place a pineapple ring in each muffin cup and add a maraschino cherry in the center of each ring.
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Prepare the Cake Batter
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In a separate bowl, whisk together flour, sugar, baking powder, and salt.
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Add the vegetable oil, egg, milk, and pineapple juice to the dry ingredients and mix until smooth.
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Fill the Muffin Cups
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Divide the batter among the muffin cups, pouring it over the pineapple rings.
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Bake and Serve
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Bake the cupcakes for 20-25 minutes, or until a toothpick inserted comes out clean.
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Let the cupcakes cool for 5 minutes before carefully inverting them onto a wire rack.
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Serve the cupcakes warm or at room temperature.
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Servings and Timing
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Servings: This recipe yields about 12 cupcakes.
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Prep time: 15 minutes
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Cook time: 20-25 minutes
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Total time: Approximately 40 minutes
Variations
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Coconut Pineapple Topping: Toast shredded coconut until golden and mix it with diced pineapple. Sprinkle with brown sugar for added sweetness.
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Tropical Fruit Medley: Mix tropical fruits like mango, kiwi, and papaya with pineapple chunks. Drizzle with a honey-lime dressing for an extra layer of flavor.
These variations allow you to experiment with different textures and flavors, from the crunchy coconut topping to a refreshing burst of tropical fruits.
Storage/Reheating
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Storage: Store any leftover cupcakes in an airtight container at room temperature for up to 3 days.
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Reheating: Reheat the cupcakes in the microwave for about 10-15 seconds or in the oven at 350°F for 5-7 minutes to warm them through.
FAQs
1. Can I use fresh pineapple instead of canned pineapple rings?
Yes, fresh pineapple can be used, but canned pineapple is often more convenient as it’s pre-sliced and already has the right moisture content for caramelization.
2. How do I prevent the cupcakes from sticking to the muffin tin?
Make sure to grease the muffin tin thoroughly or use paper liners to ensure the cupcakes release easily after baking.
3. Can I substitute the all-purpose flour with gluten-free flour?
Yes, you can use a gluten-free all-purpose flour blend as a substitute for the regular flour in this recipe.
4. Can I add other fruits like cherries to the batter?
Certainly! You can experiment by adding a few fresh or dried fruits to the batter. Just be sure not to overcrowd the batter so that the cupcakes still bake properly.
5. Can I make this recipe into a full-size cake instead of cupcakes?
Yes, you can bake this as a single cake in a 9-inch round cake pan, just adjust the baking time to 35-40 minutes.
6. How do I prevent the pineapple from turning mushy?
Be sure not to overbake the cupcakes, as this can cause the pineapple to become too soft. Also, draining the pineapple slices thoroughly before placing them in the muffin cups will help.
7. Can I freeze these cupcakes?
Yes, Pineapple Upside Down Cupcakes freeze well. Wrap them tightly in plastic wrap and store in an airtight container for up to 3 months. Thaw at room temperature when ready to enjoy.
8. What can I substitute for maraschino cherries?
You can use fresh cherries, canned cherries, or even a bit of raspberry jam for a different twist.
9. Can I use light brown sugar instead of dark brown sugar?
Yes, light brown sugar will work just fine, though the flavor will be slightly less rich than using dark brown sugar.
10. Can I make this recipe vegan?
Yes, you can substitute the egg with a flax egg (1 tbsp ground flaxseed mixed with 3 tbsp water) and use non-dairy milk (such as almond or soy milk) and oil for a vegan version.
Conclusion
Pineapple Upside Down Cupcakes are a delightful and fun twist on the traditional pineapple upside-down cake. With their moist cake base, caramelized pineapple topping, and sweet cherry finish, these cupcakes make for the perfect dessert to brighten any occasion. Simple to make yet bursting with tropical flavors, this recipe is sure to become a go-to for your next gathering. Enjoy the warm, fruity goodness with every bite!

Pineapple Upside Down Cupcakes Recipe
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Pineapple Upside Down Cupcakes offer a tropical twist with individual treats that feature caramelized pineapple and a moist, fluffy cake base.
- Total Time: 40 minutes
- Yield: 12 cupcakes
Ingredients
1/4 cup unsalted butter, melted
1/2 cup light brown sugar
4–5 slices canned pineapple rings
1/3 cup pineapple juice
1 cup all-purpose flour
3/4 cup granulated sugar
1/4 cup vegetable oil
1 large egg
1 tsp baking powder
1/2 tsp salt
1/2 cup milk
Instructions
- Preheat the oven to 350°F (175°C).
- In a bowl, combine melted butter and brown sugar, then divide the mixture evenly into the cups of a muffin tin.
- Place a pineapple ring in each muffin cup and add a maraschino cherry in the center of each ring.
- In a separate bowl, whisk together flour, sugar, baking powder, and salt.
- Add the vegetable oil, egg, milk, and pineapple juice to the dry ingredients and mix until smooth.
- Divide the batter among the muffin cups, pouring it over the pineapple rings.
- Bake the cupcakes for 20-25 minutes, or until a toothpick inserted comes out clean.
- Let the cupcakes cool for 5 minutes before carefully inverting them onto a wire rack.
- Serve the cupcakes warm or at room temperature.
Notes
- Use paper liners or thoroughly grease the muffin tin to avoid sticking.
- If using fresh pineapple, be sure to cut the slices evenly to ensure uniform baking.
- For a vegan version, substitute the egg with a flax egg and use non-dairy milk.
- If storing, place cupcakes in an airtight container at room temperature for up to 3 days.
- Author: Julia
- Prep Time: 15 minutes
- Cook Time: 20-25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: Tropical
- Diet: Vegetarian
Nutrition
- Serving Size: 1 cupcake
- Calories: 240
- Sugar: 24g
- Sodium: 150mg
- Fat: 9g
- Saturated Fat: 3g
- Unsaturated Fat: 5g
- Trans Fat: 0g
- Carbohydrates: 37g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 30mg