Pineapple Upside-Down Cupcakes

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Okay, let’s talk about dessert for a second—have you ever had a bite of something that instantly transports you to a sunny beach with the breeze in your hair? Trust me, these Pineapple Upside-Down Cupcakes do just that! Picture this: a moist, fluffy cupcake topped with sweet caramelized pineapple and a cherry, all cozy in its own little portion. Each bite is like a tiny, tropical vacation. These cupcakes aren’t just a treat; they’re a conversation starter. The combination of sweet, tangy pineapple and that golden, buttery glaze is pure magic. I promise, you’re going to fall in love with these!

Why You’ll Love Pineapple Upside-Down Cupcakes

These cupcakes are a guaranteed crowd-pleaser—whether you’re serving them at a family dinner, a picnic, or just indulging in a sweet moment by yourself. Here’s why they’re totally worth making:

  • Versatile: Perfect for any occasion! Whether it’s a birthday, a potluck, or just a sweet snack, these cupcakes fit the bill. They’re like the little black dress of desserts—good for anything and always in style.
  • Budget-Friendly: This recipe uses ingredients you probably already have in your pantry and fridge. Pineapple, butter, sugar—nothing too fancy here, but the results are definitely something to rave about!
  • Quick and Easy: You don’t need to be a baking expert to nail this one. Simple ingredients and easy steps—this recipe is perfect for those who want something impressive without all the fuss.
  • Customizable: Love coconut? Throw a little shredded coconut on top. Want a little more zing? Add a splash of lime juice. You can make this recipe your own!
  • Crowd-Pleasing: These cupcakes are always a hit. From kids to adults, everyone loves the mix of flavors and that perfect upside-down look.

Ingredients in Pineapple Upside-Down Cupcakes

These cupcakes are built from pantry staples that are so simple but create something truly delightful. Let’s break it down:

Pineapple Slices

The star of the show! Sweet, juicy pineapple slices get caramelized into a beautiful golden crown atop the cupcakes. They bring that tropical sweetness and tang that everyone loves.

Maraschino Cherries

For a pop of color and that classic “upside-down” vibe, maraschino cherries top each cupcake like a cherry on top—literally!

Butter

You can’t go wrong with butter—it adds richness and helps create that melt-in-your-mouth texture we all crave.

Brown Sugar

The brown sugar adds a deep, molasses-like sweetness to the glaze, giving the pineapple a caramelized finish that’s simply irresistible.

Cupcake Batter

Made with simple ingredients like flour, sugar, eggs, and vanilla, this batter is what holds all that pineapple goodness. It’s light, fluffy, and perfectly sweet.

(Note: The full ingredients list, including measurements, is provided in the recipe card directly below.)

Instructions

Let’s get these cupcakes into the oven so you can enjoy that tropical goodness!

Preheat Your Oven:

Start by preheating your oven to 350°F (175°C). This ensures your cupcakes bake evenly and get that golden-brown finish.

Prepare the Pan:

Grease a muffin tin or line it with cupcake liners. You want to make sure each cupcake comes out perfectly without any sticking. This also makes cleanup a breeze!

Make the Pineapple Topping:

In the bottom of each muffin cup, place a pineapple slice. Top each slice with a cherry for that classic upside-down look. Don’t be afraid to press the pineapple slice a little—this will help it bake into the cake beautifully.

Mix the Batter:

In a large bowl, whisk together the flour, sugar, baking powder, and salt. Add the wet ingredients—eggs, milk, vanilla, and melted butter—and mix until smooth and well combined.

Pour the Batter:

Carefully pour the batter over the pineapple slices, filling each cup about 2/3 full. You want the pineapple to stay at the bottom, so be gentle as you add the batter.

Bake to Perfection:

Pop the pan into the oven and bake for 20-25 minutes, or until a toothpick inserted into the center comes out clean. The tops will be golden brown, and your kitchen will smell heavenly.

Flip and Serve:

Once your cupcakes have cooled slightly, it’s time to flip them over! Place a serving plate over the muffin tin and carefully flip it. You’ll reveal those beautiful caramelized pineapple tops. Let them cool for a few more minutes and then serve!

How to Serve Pineapple Upside-Down Cupcakes

These cupcakes are perfect on their own, but here are some fun ways to take them to the next level:

  • With a Scoop of Vanilla Ice Cream: Warm pineapple upside-down cupcakes with a scoop of creamy vanilla ice cream are the ultimate dessert duo. The cold ice cream complements the warm cake, creating a perfect bite every time.
  • Topped with Whipped Cream: A dollop of fresh whipped cream adds a touch of sweetness and lightness to balance the richness of the pineapple topping.
  • As a Picnic Treat: These cupcakes are portable and perfect for outdoor gatherings. Pack them up for your next picnic or road trip for a sweet, homemade snack on the go.

Additional Tips

  • Prep Ahead: You can prep the pineapple topping and batter in advance. Just store the ingredients separately in the fridge and assemble them when you’re ready to bake.
  • Go Tropical: Add some shredded coconut to the batter for a coconut-pineapple twist that’s even more tropical!
  • Storage Tips: Store leftovers in an airtight container at room temperature for up to 2 days. They also freeze beautifully for up to 2 months.
  • Double the Batch: This recipe is perfect for making a double batch, especially when you’re hosting a party or picnic. You’ll definitely need more than one batch of these!

FAQ Section

Q1: Can I substitute pineapple with another fruit? A1: Sure! You can swap the pineapple for peaches, mangoes, or even strawberries. Just keep in mind the cooking time might need to be adjusted depending on the fruit.

Q2: Can I make these cupcakes in advance? A2: Yes, these cupcakes keep well in an airtight container for up to 2 days. You can even freeze them and enjoy them later!

Q3: How do I store leftovers? A3: Store any leftovers in an airtight container at room temperature for up to 2 days. You can also freeze them for longer storage.

Q4: Can I use fresh pineapple instead of canned? A4: Absolutely! Just make sure to cut it into slices and remove the core before using it.

Q5: What’s the best way to reheat these cupcakes? A5: Warm them up in the microwave for 10-15 seconds or in the oven at 300°F (150°C) for about 5 minutes.

Q6: Can I make this recipe gluten-free? A6: Yes, you can substitute a gluten-free flour blend for the regular flour. Just make sure to double-check that the other ingredients are gluten-free.

Q7: Can I make a larger version of this as a cake? A7: Definitely! Just use a larger baking pan and adjust the baking time accordingly. You’ll want to bake it until a toothpick inserted into the center comes out clean.

Q8: How do I prevent the pineapple from sticking to the pan? A8: Grease your pan thoroughly and use parchment paper for added protection. This will help ensure the pineapple comes out cleanly.

Q9: Can I make this without the cherries? A9: Of course! The cherries are optional, but they do add a nice pop of color and flavor. You can skip them if you prefer.

Q10: Can I add spices like cinnamon or nutmeg to the batter? A10: Absolutely! A pinch of cinnamon or nutmeg would complement the pineapple beautifully and add a warm, cozy flavor to the cupcakes.

Conclusion

These Pineapple Upside-Down Cupcakes are perfect for anyone craving something sweet, simple, and unforgettable. Whether you’re making them for a special occasion or just because you need a treat, they’re sure to bring smiles to every face. So go ahead—let your oven fill your home with tropical vibes, and enjoy each sweet, sticky bite!

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Pineapple Upside-Down Cupcakes

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These Pineapple Upside-Down Cupcakes are a fun and individual twist on the classic dessert! With a delicious layer of caramelized brown sugar, juicy pineapple, and a sweet maraschino cherry, these cupcakes will transport you straight to paradise! Perfect for a summer treat or any time you’re craving a tropical indulgence

  • Prep Time: 15 minutes
  • Cook Time: 25 minutes
  • Total Time: 40 minutes
  • Yield: 12 cupcakes 1x
  • Category: Dessert, Cakes, Cupcakes
  • Method: Baking
  • Cuisine: American, Tropical
  • Diet: Vegetarian

Ingredients

Scale
  1. (Makes 12 cupcakes)
  2. For the Topping:
  3. ¼ cup (60g) unsalted butter, melted
  4. ½ cup (100g) light brown sugar
  5. 6 canned pineapple rings, halved
  6. 12 maraschino cherries
  7. For the Cake Batter:
  8. 1 ½ cups (190g) all-purpose flour
  9. 1 teaspoon baking powder
  10. ½ teaspoon baking soda
  11. ¼ teaspoon salt
  12. ½ cup (115g) unsalted butter, softened
  13. ¾ cup (150g) granulated sugar
  14. 2 large eggs
  15. 1 teaspoon vanilla extract
  16. ½ cup (120ml) pineapple juice (reserved from the can)
  17. ½ cup (120ml) buttermilk (or milk with 1 teaspoon vinegar/lemon juice)

Instructions

  1. Preheat the Oven
    Preheat your oven to 350°F (175°C). Grease or line a 12-cup muffin tin.
  2. Make the Topping
    In a small bowl, mix the melted butter and brown sugar.
    Spoon about 1 teaspoon of the mixture into the bottom of each muffin cup.
    Place a halved pineapple ring in each cup and press it slightly into the sugar mixture. Add a maraschino cherry in the center of each pineapple.
  3. Prepare the Cake Batter
    In a medium bowl, whisk together the flour, baking powder, baking soda, and salt.
    In a large mixing bowl, beat the softened butter and granulated sugar until light and fluffy, about 2–3 minutes.
    Add the eggs, one at a time, mixing well after each addition. Stir in the vanilla extract.
    Gradually mix in the dry ingredients, alternating with the pineapple juice and buttermilk, beginning and ending with the dry ingredients. Mix just until combined.
  4. Assemble the Cupcakes
    Divide the batter evenly among the muffin cups, filling each about three-quarters full over the pineapple and cherry topping.
  5. Bake
    Bake in the preheated oven for 20–25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
    Allow the cupcakes to cool in the pan for 5 minutes.
  6. Flip and Cool
    Place a wire rack or large baking sheet over the muffin tin. Carefully invert the pan to release the cupcakes, allowing the topping to reveal itself.
    Let the cupcakes cool completely before serving.

Notes

  • Ensure the cupcakes are fully cooled before flipping, as this helps preserve the shape of the topping.
  • For an extra touch, add a small dollop of whipped cream on top when serving.

Nutrition

  • Serving Size: 1 cupcake
  • Calories: 260 kcal
  • Sugar: 26g
  • Sodium: 150mg
  • Fat: 12g
  • Saturated Fat: 7g
  • Unsaturated Fat: 4g
  • Trans Fat: 0g
  • Carbohydrates: 35g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 50mg

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