There are some recipes that just *feel* like home, aren’t there? For me, one of those is definitely upside down cupcakes. Now, I know what you might be thinking – “aren’t those just pineapple upside down cakes in a different shape?” And yes, kind of! But trust me, there’s something magical about having all that gooey, caramelized goodness baked right into a perfectly portioned little cupcake. It’s a game-changer, especially when you want that comforting, classic flavor without the fuss of slicing a whole cake. My kids, bless their hearts, ask for these “little pineapple swirls” all the time, and honestly, they disappear in minutes. This recipe has been in my family for years, with a few little tweaks I’ve picked up along the way that just make them absolutely irresistible. It’s the perfect balance of sweet, tangy pineapple and a tender, moist cake that I just can’t get enough of. If you’ve ever felt intimidated by making a traditional pineapple upside down cake, or just want a fun, handheld version, then you are in for such a treat!
What is an upside down cupcake?
So, what exactly are upside down cupcakes? Think of your favorite pineapple upside down cake, but miniaturized and made even more convenient. Instead of baking the caramel and pineapple in one large pan, we’re carefully layering that delicious topping into the bottom of our muffin tins before spooning the cake batter on top. Once they’re baked and cooled just a bit, you flip them out, and *voilà!* – you have these gorgeous little treats with that sticky, sweet, caramelized pineapple crown peeking out. It’s essentially a delightful surprise waiting for you with every bite. The beauty of it is that the pineapple and the butter-sugar topping create their own little flavor bomb that infuses right into the bottom of the cupcake, making it incredibly moist and decadent. It’s a classic dessert, reinvented for easier serving and maximum enjoyment!
Why you’ll love this recipe?
Honestly, the reasons I keep coming back to this recipe are so many! Firstly, the flavor. Oh my goodness, the flavor! You get that bright, slightly tart sweetness from the pineapple, perfectly balanced by the rich, buttery caramel topping that bakes up with a beautiful, almost toffee-like crust. It’s not overwhelmingly sweet, which I really appreciate. Then there’s the cake itself – it’s incredibly tender and moist, almost melt-in-your-mouth good. I’ve tried this with different variations, and it always holds up beautifully. And speaking of simplicity, this recipe is a lifesaver on busy nights. It’s much less daunting than a full-sized cake, and the prep time is really quite manageable. You can even get the kids involved in putting the pineapple slices in the tins, which they absolutely love. Plus, it’s so cost-effective! Canned pineapple rings and basic pantry staples are all you need. What I love most about these upside down cupcakes is their incredible versatility. They’re perfect for a casual weekend breakfast treat, elegant enough for a brunch spread, and absolutely divine as a dessert. They even make a fantastic afternoon pick-me-up when you just need a little something sweet without committing to a whole slice of cake. It’s a comfort food that looks a little bit fancy, which is always a win in my book!
How do I make upside down cupcakes?
Quick Overview
Making these upside down cupcakes is surprisingly straightforward and incredibly rewarding. You’ll start by creating that signature caramelized pineapple topping right in your muffin cups, then pour over a simple, tender cake batter. After a bake in the oven, you’ll flip them out to reveal a beautiful, gooey crown. It’s a process that takes a little care, but the results are absolutely worth it, and it’s so much less intimidating than a full-sized upside down cake. You get all the classic flavors in a perfectly portioned package that’s ready to impress!
Ingredients
For the Main Batter:
1 ½ cups all-purpose flour
1 teaspoon baking powder
½ teaspoon baking soda
¼ teaspoon salt
½ cup unsalted butter, softened
1 cup granulated sugar
2 large eggs, at room temperature
1 teaspoon vanilla extract
½ cup buttermilk, at room temperature (or ½ cup milk + ½ tsp lemon juice, let sit for 5 mins)
*Tip: Using room temperature ingredients for the batter really helps everything emulsify beautifully, leading to a lighter, more tender cake.*
For the Filling:
1 can (20 ounces) pineapple rings (about 8-10 rings)
½ cup packed light brown sugar
¼ cup unsalted butter
Maraschino cherries, for garnish (optional)
*Tip: Pat your pineapple rings dry with a paper towel. This helps the caramel form nicely without steaming.*
For the Glaze:
1 cup powdered sugar
2-3 tablespoons milk or pineapple juice
½ teaspoon vanilla extract
*Tip: You want the glaze to be pourable but not too thin. It should coat the back of a spoon nicely.*
Step-by-Step Instructions
Step 1: Preheat & Prep Pan
First things first, let’s get our oven fired up to 350°F (175°C). Line a standard 12-cup muffin tin with paper liners. This is crucial because we’re going to be flipping these out later, and the liners help prevent sticking and make cleanup a breeze. If you don’t have liners, make sure your muffin tin is very well-greased and floured. I always do an extra little spritz of cooking spray inside the paper liners for good measure – never had a problem with sticking since I started doing that!
Step 2: Mix Dry Ingredients
In a medium bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt. Give it a good whisk to make sure everything is evenly distributed. This little step might seem minor, but it ensures your leavening agents are spread out perfectly, leading to an even rise and a lovely texture. Set this aside for now.
Step 3: Mix Wet Ingredients
In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. This usually takes a few minutes with an electric mixer. Then, beat in the eggs one at a time, making sure each is fully incorporated before adding the next. Stir in the vanilla extract. In a separate small bowl or jug, combine the buttermilk. Gradually add the dry ingredients to the wet ingredients alternately with the buttermilk, beginning and ending with the dry ingredients. Mix just until combined – it’s important not to overmix here, as that can lead to tough cupcakes.
Step 4: Combine
Now we bring it all together. Add about a third of the dry ingredients to the butter mixture and mix on low speed. Then add half of the buttermilk and mix. Repeat this process, alternating dry and wet, until everything is just incorporated. Give it a final gentle stir with a spatula to make sure there are no dry pockets at the bottom of the bowl. Remember, we’re aiming for a tender cake, so a light hand is best!
Step 5: Prepare Filling
This is where the magic begins! In a small saucepan over medium heat, melt the ¼ cup of butter. Once melted, stir in the ½ cup of packed light brown sugar until it’s smooth and combined. Cook for just a minute or two until it’s bubbly and slightly thickened. Pour about a tablespoon of this brown sugar mixture into the bottom of each muffin cup. Then, place one pineapple ring on top of the brown sugar mixture in each cup. If you have any gaps, you can break up pieces of pineapple to fill them. If you’re using cherries, pop one in the center of each pineapple ring. This caramel layer is going to be the crowning glory!
Step 6: Layer & Swirl
Carefully spoon the cake batter evenly over the pineapple rings in each muffin cup. Fill each cup about two-thirds of the way full. You don’t want to overfill them, as they will rise as they bake. I like to gently tap the muffin tin on the counter a couple of times to settle the batter and release any large air bubbles. This helps create a nice, even surface for baking.
Step 7: Bake
Pop the muffin tin into your preheated oven. Bake for 20-25 minutes, or until a wooden skewer or toothpick inserted into the center of a cupcake comes out clean. The edges should be golden brown. Keep an eye on them towards the end of baking – ovens can be so finicky! Once they’re done, carefully remove the muffin tin from the oven.
Step 8: Cool & Glaze
This is the trickiest part, but it’s where the “upside down” magic happens! Let the cupcakes cool in the muffin tin for about 5-10 minutes. This is important – too soon and they might fall apart; too long and they’ll stick. While they’re cooling, whisk together the powdered sugar, 2 tablespoons of milk (or pineapple juice), and vanilla extract in a small bowl. Add more milk, a teaspoon at a time, until you reach a smooth, pourable consistency. Once the cupcakes have cooled slightly, carefully invert the muffin tin onto a wire rack to release the cupcakes. If any pineapple or caramel sticks in the pan, gently scoop it out and place it back on top of the cupcake. Once the cupcakes have cooled a bit more (they should still be warm but not hot), drizzle the glaze over the top of each one. This glaze adds an extra touch of sweetness and shine, and it’s just lovely!
Step 9: Slice & Serve
Once the glaze has set a little, your upside down cupcakes are ready to be enjoyed! They are absolutely delicious served warm, just as they are. The warm, gooey pineapple and the tender cake are pure comfort. You can serve them as is, or with a dollop of whipped cream or a small scoop of vanilla Ice Cream for an extra treat. They also hold up beautifully at room temperature, making them a great option for picnics or packed lunches.
What to Serve It With
These upside down cupcakes are wonderfully versatile, fitting in perfectly at any meal or occasion! For a delightful breakfast, they’re heavenly alongside a steaming mug of coffee or a glass of fresh orange juice. The sweet, tangy pineapple is just the right wake-up call. For a more festive brunch, I love to arrange them on a tiered stand with fresh fruit and a mimosa. The vibrant colors are so appealing! As a dessert, they shine brightly. Imagine serving them warm with a scoop of creamy vanilla bean ice cream or a dollop of freshly whipped cream. It’s a classic pairing that never disappoints. And for those cozy afternoon snack cravings, they are the ultimate comfort. A warm cupcake and a glass of milk, or a cup of tea, is pure bliss. My family has a tradition of having these on Sunday mornings, and it just makes the day feel extra special. They also disappear ridiculously fast when we have friends over for a casual get-together – a testament to how universally loved they are!
Top Tips for Perfecting Your Upside Down Cupcakes
Over the years, I’ve learned a few little tricks that make these upside down cupcakes consistently amazing. For the pineapple, I always use canned rings because they’re uniform and easy to work with. Make sure to pat them as dry as possible with paper towels before placing them in the muffin tin. This prevents the caramel from becoming watery and ensures it gets that lovely, slightly crisp texture. When you’re making the cake batter, don’t overmix once you add the flour. Just mix until everything is *just* combined. A few little lumps are okay! Overmixing develops the gluten too much, which can lead to a tough, dense cupcake. I’ve learned this the hard way after a few batches that weren’t as tender as I’d hoped. For the swirling and layering, ensure you get a good amount of that brown sugar-butter mixture into each cup. This is what creates that fantastic sticky, caramelized layer. If some pineapple pieces don’t fit perfectly, don’t worry! Breaking them up and filling the gaps works just fine. For baking, every oven is a little different, so keep an eye on them. The toothpick test is your best friend here – it should come out clean, with maybe a few moist crumbs attached, but no wet batter. If your cupcakes are browning too quickly on top, you can loosely tent them with foil. For the glaze, the key is consistency. You want it thick enough to coat nicely but thin enough to drizzle. Start with 2 tablespoons of liquid and add more only if needed, a teaspoon at a time. If it’s too thin, you can whisk in a little more powdered sugar. If it’s too thick, a tiny bit more liquid will do the trick. These little adjustments really make a difference!
Storing and Reheating Tips
One of the things I adore about these upside down cupcakes is how well they store. If you have any leftovers (which is rare in my house!), you can keep them at room temperature for up to 2 days. Just make sure they are in an airtight container to keep them fresh. The glaze will help seal in some moisture. If you think you’ll have them for longer, or if your kitchen is particularly warm, they’ll do wonderfully in the refrigerator for up to 4 days. I usually pop them into an airtight container or wrap the muffin tin loosely with plastic wrap. When you’re ready to enjoy them from the fridge, you can eat them cold, or if you prefer them warm, a quick zap in the microwave for about 10-15 seconds is usually enough to bring back that lovely warmth and gooeyness. For longer storage, these cupcakes freeze beautifully! Let them cool completely, then wrap each one individually in plastic wrap, followed by a layer of aluminum foil or a freezer-safe bag. They’ll stay good in the freezer for up to 2 months. Thaw them overnight in the refrigerator or at room temperature, and reheat as desired. I often add the glaze *after* they’ve been stored and reheated, just to keep it looking its best, especially if they’ve been frozen.
Frequently Asked Questions
Final Thoughts
There you have it – my absolute favorite way to enjoy the classic pineapple upside down flavor! These cupcakes are more than just a dessert; they’re little pockets of sunshine and comfort that always bring a smile to my face. The way the moist cake meets that gooey, caramelized pineapple is just pure magic. They’re proof that sometimes, the simplest recipes can be the most impactful, especially when they’re made with a little bit of love and a few well-tested tips. I really hope you’ll give these upside down cupcakes a try. They’re perfect for special occasions, or just for making an ordinary day feel a little bit brighter. If you love this recipe, you might also enjoy my Lemon Blueberry Muffins or my Classic Chocolate Chip Cookies, which are also family favorites. I can’t wait to hear how yours turn out, so please leave a comment below and share your thoughts, or any fun variations you tried! Happy baking!
Pineapple Upside Down Cupcakes
Ingredients
For the Topping
- 0.083 cup canned pineapple chunks (divided)
- 2 tablespoons brown sugar
For the Cupcakes
- 1.5 cups all-purpose flour
- 0.333 cup unsweetened shredded coconut
- 2 teaspoons baking powder
- 0.5 teaspoon kosher salt
- 0.333 cup coconut oil
- 0.75 cup granulated sugar
- 1 teaspoon almond extract
- 0.75 cup pineapple juice
- 2 large eggs
Instructions
Preparation Steps
- Preheat the oven to 350°F (175°C) and spray a muffin tin with cooking spray. Set aside.
- In a medium bowl, whisk together the flour, shredded coconut, baking powder, and salt. Set aside.
- In a large bowl, beat the coconut oil with an electric mixer on high speed until smooth. Add the granulated sugar and almond extract, and mix until light and fluffy.
- Slowly pour the pineapple juice into the coconut oil and sugar mixture and mix on low speed. The mixture may not be completely homogenous and the coconut oil might congeal slightly, which is okay.
- Add the eggs one at a time, beating until just combined after each addition.
- Gradually add the dry ingredients to the wet ingredients on low speed, scraping down the sides of the mixing bowl a few times. Do not overmix.
- Toss the pineapple chunks with the brown sugar. Place about 1 tablespoon of the pineapple mixture into the bottom of each muffin cup.
- Scoop about 3 heaping tablespoons of batter into each muffin cup, on top of the pineapple mixture.
- Bake for 18-22 minutes, or until a toothpick inserted into the center comes out clean.
- Let the cupcakes cool in the muffin tin for 5 minutes before carefully inverting them onto a wire rack to cool completely.
