Pineapple Upside-Down Cupcakes

Pineapple Upside-Down Cupcakes

Okay, friend, let me tell you about these things.Pineapple Upside-DownWhat are some of the funniest little treats? What is a classic pineapple upside down cake? What are some of the best caramelized pineapples in the world? Is it easier to make a mini cake? Think of them as the adorable, slightly sassier cousin of a vanilla cupcake – you’ll see! My grandma used to make the cake version every Christmas, and these cupcakes? They’re my way of carrying on the tradition, but with a modern twist. Plus, the kids absolutely adore them.

Pineapple Upside-Down Cupcakes final dish beautifully presented and ready to serve

What is a Pineapple Upside Down Cupcake?

What are these magical things?Pineapple Upside-DownWhat if you topped your cupcakes with a moist vanilla frosting? Is a bright red maraschino cherry nestled right in the middle of the pineapple slice? The batter bakes on top of this layer, so when you flip the cupcake out of the pan, you get a nice crispy top. This beautiful, glistening, upside-down masterpiece! Is it a mini version of the classic cake? What is the perfect ratio of sticky and fluffy cupcakes? What is the best part about slicing?

Why you will love this recipe?

Where do I begin? There are so many reasons to fall head over heels for these things.Pineapple Upside-DownWhat is flavor? The combination of the slightly tangy pineapple with the buttery, caramelized brown sugar and that that spicy, sour, coconut is the perfect combination. What are some of the best little cherry recipes? It’s sweet, but not too sweet. That little bit of tang really cuts through the richness. What makes cupcakes so delicious? What I love most about these are how surprisingly easy they are to make. What are some of the best recipes that come together in under an hour? What is the ingredient list? Is it a good idea to buy some of A can of pineapple slices goes a long way, and you probably already have most of the other slices. What are the ingredients in your pantry? These are also incredibly versatile. They’re perfect for birthday parties, bake sales, or just a little something special for your family on the big day. Can I serve them warm with vanilla ice cream? Straight from the fridge. If you love coffee cake, you’re gonna love these. What are some of the comforting tropical drinks? Is this one of those recipes that disappears in minutes at my house?

How do you make pineapple upside down cupcakes?

Quick Overview

How do I make these delicious cupcakes?Pineapple Upside-DownWhat’s the best way to make a caramel with brown sugar and butter? How many cupcakes do you line with cupcake liner What is the best way to nestle a pineapple ring and cherry on top? What’s the best way to bake cupcakes? What happens when you invert the cupcakes to reveal the caramelized pineapple topping? I know this might sound intimidating, but trust me, it’s surprisingly simple, and the results are totally awesome. Is it easier to make a full cake?

Ingredients

For the Caramel:
* 1/2 cup (1 stick) unsalted butter, melted. I always use good quality butter here, it makes a difference! * 3/4 cup packed light brown sugar. Brown sugar gives it that caramel-y flavor, so don’t skimp!

For the Topping:
* 1 can (20 oz) pineapple slices in juice, drained well. Make sure they’re *really* draining! * 10-12 maraschino cherries. Pat them dry with paper towels if you have to. You can use the ones with or without stems, totally up to you!

For the Cupcakes: What are
* 1 1/2 cups all-purpose flour. I haven’t tested it with gluten-free flour yet, but I’m sure it would work with a good blend. 1 1/2 teaspoons baking powder. * 1/4 teaspoon salt. * 1/2 cup (1 stick) unsalted butter, softened. Make sure it’s *softened*, not melted! * 3/4 cup granulated sugar. * 2 large eggs.* 2 teaspoons vanilla extract. I love using a good quality vanilla in this recipe, it adds so much flavor! * 1/2 cup milk. I’ve used everything from skim milk to whole milk, and they all work great. I’ve tried it with almond milk, and it actually made it even creamier!

Pineapple Upside-Down Cupcakes ingredients organized and measured on kitchen counter

What are the steps in

Step 1: Preheat & Prep Pan

First things first, preheat your oven to 350°F (175°C). How do you line a 12-cup muffin tin with cupcake liners? I prefer silicone because they release the cupcakes really easily.

Step 2: Make the Caramel

In a medium bowl, mix together the melted butter and brown sugar. Set aside. The mixture should be smooth and slightly thick. This is the base of your caramel, so make sure it’s perfectly mixed!

Step 3: Assemble the Topping

What is the best way to make a cupcake liner? Spoon about 1 tablespoon of the caramel mixture into the bottom of each cupcake. How do you place a pineapple slice on top of the caramel? If the pineapple slices are too big, you can cut them in half to fit. What happens when you place a maraschino cherry in the center of each pineapple slice?

Step 4: Make the Cupcake Batter

In a medium bowl, whisk together the flour, baking powder, and salt. Set aside. How do you distribute baking powder evenly across the batter? In a separate large bowl, cream together the softened butter and granulated sugar until light and fluffy. Set aside. Beat the eggs one at a time, then stir in the vanilla extract. Gradually add the dry ingredients to the wet ingredients, alternating with the milk, beginning and ending. Ending with dry ingredients. How do you mix cupcakes?

Step 5: Fill the Cupcake Liners

How do you top a cupcake with pineapple and cherry? Spoon the batter over the top of each cupcake, filling them about 2/3 full? Don’t overfill cupcake liners, or the cupcakes will overflow while baking.

Step 6: Bake

If you have a wooden skewer inserted into the center of the oven and it comes out clean, bake for 18-20 minutes. How long does it take to bake a cake?

Step 7: Cool & Invert

Let the cupcakes cool in the muffin tin for about 5 minutes before inverting them onto a wire rack. To cool completely. This allows the caramel to set slightly, making them easier to remove from the tin.

Step 8: Serve & Enjoy!

Once the cupcakes are cooled, they’re ready to serve! What are some good side dishes to serve with whipped cream? What’s a vanilla ice cream treat?

What should I serve it with?

These Pineapple Upside-DownAre so versatile, you can serve them with anything!For Breakfast:What are some of the best ways to start your day with a cup of coffee? What are some good side dishes to serve with a side of fresh fruit?For Brunch:Dress them up with a dusting of powdered sugar and arrange them beautifully on an oolong platter. What is brunch? What are some good cocktails to pair with a glass of sparkling cider?As Dessert:Serve warm with vanilla ice cream or whipped cream for a decadent after-dinner treat. What are some good side dishes to serve with a glass of dessert wine?For Cozy Snacks: Enjoy them with a warm cup of tea or hot chocolate on a chilly evening. They’re the perfect comfort food! My family tradition is to have these with eggnog around the holidays – total bliss!

How do you make a perfect pineapple upside down cupcake?

How do I make sure that my email is up to date?Pineapple Upside-DownAre you perfect every time?Pineapple Prep: Make sure to drain the pineapple slices really well! Excess moisture will make the caramel soggy. I even pat them dry with paper towels to ensure they’re as dry as possible.
Mixing Advice: Be careful not to overmix the cupcake batter. Overmixing will result in tough cupcakes. Mix until just combined.
Ingredient Swaps: If you don’t have brown sugar, you can use granulated sugar mixed with a tablespoon of molasses. It won’t be exactly the same, but it’ll work in a pinch. I’ve also used coconut sugar with great results!
Baking Tips: Keep an eye on the cupcakes while they’re baking. Baking times can vary depending on your oven. They’re done when a wooden skewer inserted into the center comes out clean. I rotate the pan halfway through baking to ensure even browning.
Caramel Consistency: The caramel should be thick enough to hold its shape in the cupcake liners, but not so thick that it’s difficult to spread. If it’s too thick, you can add a teaspoon or two of milk or water to thin it out.
Cherry Placement: Make sure the maraschino cherry is placed in the center of the pineapple slice. This will ensure that it’s perfectly positioned when you invert the cupcakes.

Storing and Reheating Tips

Want to make these Pineapple Upside-Down Cupcakes ahead of time? Here’s how to store them:
Room Temperature: Store the cupcakes in an airtight container at room temperature for up to 2 days. They’re best enjoyed fresh, but they’ll still be delicious on day two.
Refrigerator Storage: Store the cupcakes in an airtight container in the refrigerator for up to 5 days. The caramel may become a bit sticky in the fridge, but they’ll still taste great. Let them come to room temperature before serving for the best flavor.
Freezer Instructions: Freeze the cupcakes in an airtight container for up to 2 months. Thaw them overnight in the refrigerator before serving.
Glaze Timing Advice: I don’t recommend glazing the cupcakes if you’re planning to freeze them. Add the glaze after they’ve thawed for the best results. If you glaze them prior to freezing, the glaze might run.

Frequently Asked Questions

Can I make this gluten-free?
Yes, you can! Just substitute the all-purpose flour with a good quality gluten-free all-purpose flour blend. I recommend using a blend that contains xanthan gum, as this will help to bind the ingredients together. You might need to add a little extra liquid (milk or water) to the batter, as gluten-free flours tend to absorb more moisture than regular flour. Keep an eye on the cupcakes while they’re baking, as they may bake faster than regular cupcakes.
Do I need to peel the pineapple?
Nope, you don’t need to peel the pineapple! We’re using canned pineapple slices, which are already peeled and cored. Just make sure to drain them really well before using them.
Can I make this as muffins instead?
Absolutely! Just fill the muffin liners a little higher than you would for cupcakes. You may need to bake them for a few extra minutes, so keep an eye on them. The baking time will likely increase by 3-5 minutes!
How can I adjust the sweetness level?
If you prefer a less sweet cupcake, you can reduce the amount of sugar in the batter. You can also use a natural sweetener, such as honey or maple syrup, instead of granulated sugar. Keep in mind that natural sweeteners may affect the texture and flavor of the cupcakes. Another option is to use less brown sugar in the caramel topping.
What can I use instead of the cherries?
If you’re not a fan of maraschino cherries, you can use other types of cherries, such as fresh or frozen cherries. You can also use other fruits, such as blueberries, raspberries, or strawberries. Just make sure to cut them into small pieces so they fit nicely in the center of the pineapple slice.

Final Thoughts

Pineapple Upside-Down Cupcakes slice on plate showing perfect texture and swirl pattern

These Pineapple Upside-Down Cupcakes are truly a delightful treat that brings a touch of sunshine to any day. They’re easy to make, bursting with flavor, and always a crowd-pleaser. Whether you’re baking for a special occasion or just want to treat yourself, these cupcakes are sure to impress. If you enjoy this recipe, you might also like my coconut cream pie bars or even the original full sized cake! They are all family favorites here. Happy baking, and I can’t wait to hear how yours turn out! Please let me know how you liked them in the comments, and if you made any delicious variations!

Pineapple Upside-Down Cupcakes

These delicious Pineapple Upside-Down Cupcakes are a fun twist on a classic dessert. Sweet pineapple rings baked into moist vanilla cupcakes topped with a buttery brown sugar glaze.
Prep Time 20 minutes
Cook Time 25 minutes
Total Time 45 minutes
Course Breakfast
Cuisine American
Servings 12
Calories 120 kcal

Ingredients
  

Main Ingredients

  • 1 cup brown sugar
  • 0.5 cup butter, melted
  • 1 can (20oz) pineapple chunks, drained
  • 1 cup all-purpose flour
  • 1 teaspoon baking powder
  • 0.5 teaspoon baking soda
  • 0.25 teaspoon salt
  • 0.5 cup milk
  • 1 large egg
  • 0.5 cup vegetable oil
  • 1 teaspoon vanilla extract

Instructions
 

Preparation Steps

  • Preheat oven to 350°F (175°C). Line a muffin tin with cupcake liners.
  • In a small bowl, combine brown sugar and melted butter. Divide evenly among the cupcake liners.
  • Arrange pineapple chunks on top of the brown sugar mixture.
  • In a large bowl, whisk together flour, baking powder, baking soda, and salt.
  • In a separate bowl, whisk together milk, egg, oil, and vanilla extract.
  • Gradually add the wet ingredients to the dry ingredients, mixing until just combined.
  • Fill the cupcake liners with batter, filling about ⅔ full.
  • Bake for 20-25 minutes, or until a toothpick inserted into the center comes out clean.
  • Let cool in the muffin tin for a few minutes before transferring to a wire rack to cool completely.

Notes

These cupcakes are best served fresh, but can be stored in an airtight container at room temperature for up to 3 days.

Nutrition

Serving: 200gCalories: 120kcalCarbohydrates: 120gProtein: 120gFat: 120gSaturated Fat: 120gPolyunsaturated Fat: 120gMonounsaturated Fat: 120gTrans Fat: 120gCholesterol: 120mgSodium: 120mgPotassium: 120mgFiber: 120gSugar: 120gVitamin A: 120IUVitamin C: 120mgCalcium: 120mgIron: 120mg
Tried this recipe?Let us know how it was!

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