There are desserts that feel fancy, and then there are desserts that feel like home. Pineapple Upside Down Cupcakes land squarely in that second category for me. They are warm, nostalgic, a little sticky in the best way, and always met with smiles.
I grew up eating the classic cake at family gatherings, usually when the table was already full of food and laughter. The smell of pineapple and brown sugar baking together still stops me in my tracks every single time. Turning that memory into cupcakes felt like the right move.
These cupcakes keep everything I love about the original. The caramelized fruit, the soft yellow cake, the cherry on top that somehow makes it feel special. The only difference is that everyone gets their own perfect little serving.
I also love how practical they are. No slicing, no plates balancing on knees, no crumbs everywhere. Just flip, serve, and watch them disappear faster than you expected.
If you are bringing dessert to a BBQ, a holiday dinner, or even just making something cheerful on a random afternoon, these Pineapple Upside Down Cupcakes fit right in. They feel familiar, but still a little fun.
Ingredients Needed for the Recipe
- Pineapple rings with juice reserved – the star flavor and the fruity topping that caramelizes.
- Yellow cake mix – creates a soft, reliable base that lets the pineapple shine.
- Vegetable oil – keeps the cupcakes moist and tender.
- Eggs – help bind the batter and give structure.
- Melted butter – mixes with brown sugar to form that gooey topping.
- Brown sugar – adds richness and helps caramelize the fruit.
- Maraschino cherries – a sweet pop of color and classic finishing touch.
Using a cake mix here is not about cutting corners. It is about consistency and ease, especially when the topping already brings so much flavor. The pineapple juice replaces water, and that one small change makes a big difference.
Everything on this list is easy to find, and chances are you already have most of it waiting in your pantry. That is part of what makes this recipe such a repeat favorite in my kitchen.
How to make Pineapple Upside Down Cupcakes?
Step 1 – Prepare the oven and pan
Start by preheating the oven to 350°F so it is ready when the batter is done. Spray two muffin tins generously, making sure to coat the bottoms well. This step matters more than you think.
The sugary topping needs a clean release later, and skipping this can turn flipping into a stressful moment. I learned that lesson once, and once was enough.
Step 2 – Mix the cake batter
In a large bowl, combine the yellow cake mix, eggs, vegetable oil, and reserved pineapple juice. Stir until the batter is smooth and evenly blended, with no dry pockets hiding at the bottom.
The pineapple juice adds a subtle brightness to the cake. It does not overpower anything, but it gives the crumb a gentle tropical note that feels intentional.
Step 3 – Prepare the fruit topping
Cut each pineapple ring into four even pieces so they fit neatly into the muffin wells. In a separate bowl, stir together the melted butter and brown sugar until thick and glossy.
Spoon about a teaspoon of this mixture into each muffin cup. Place two pineapple pieces on top and add half a cherry, cut side facing up.
Step 4 – Add the batter
Carefully spoon the cake batter over the fruit, filling each cup until it is about a quarter inch from the top. Try not to overfill, since the cupcakes will rise as they bake.
The batter may look plain at this stage, but trust the process. All the magic happens once they are flipped.
Step 5 – Bake and cool
Bake for 20 to 25 minutes, until the tops are golden and a toothpick comes out clean with a few moist crumbs. Let the cupcakes cool in the pan for about 15 minutes.
This short cooling time helps everything set while keeping the topping soft enough to release easily.
Step 6 – Flip and serve
Run a knife gently around the edges of each cupcake to loosen them. Place a cooling rack or tray over the pan, then flip it in one confident motion.
Let the pan sit for a minute before lifting it away. The cupcakes should slide out with their glossy pineapple tops right where they belong.
Serving Ideas
These cupcakes are best served slightly warm, when the topping is still soft and fragrant. A dollop of freshly whipped cream on the side is simple and perfect.
If you are serving them at a party, I like to set them out on a large platter so the golden pineapple really stands out. They do not need extra decoration.
For a more casual treat, they are just as good straight from the fridge the next day. The flavors mellow a bit, and the cake stays wonderfully moist.
Tips
- Do not use paper cupcake liners, since they will stick to the topping.
- Silicone liners work if you prefer an extra layer of insurance.
- Make sure the pineapple juice measures one full cup for the batter.
- If juice runs short, add water to reach the right amount.
- Flip the cupcakes while they are still warm, not fully cooled.
- Use a gentle hand when loosening the edges to keep them intact.
Flipping can feel intimidating the first time, but it gets easier with practice. The key is timing and patience, not force.
Once you see how easily they release, that fear fades quickly. It is one of those moments that feels oddly satisfying.
Simple Variations to Try
If you want to switch things up, there are plenty of small tweaks that still keep the heart of the recipe intact. Pineapple chunks or tidbits work just as well as rings.
You can also use crushed pineapple for a more rustic look. Just be sure it is well drained so the topping does not become watery.
For extra pineapple flavor, a pineapple-flavored cake mix can replace the yellow mix. It leans sweeter and brighter, which some people love.
Occasionally, I sprinkle a pinch of cinnamon into the brown sugar mixture. It adds warmth without changing the classic feel.
Storing and Freezing
Once cooled, store the cupcakes in an airtight container in the refrigerator. They stay fresh for about three days and still taste great.
If you want to freeze them, let the cupcakes cool completely first. Place them in the freezer uncovered for about an hour to firm up.
Wrap each cupcake tightly in plastic wrap, then again in foil, or place them in a freezer-safe container. Label them and freeze for up to three months.
To serve, thaw them in the refrigerator and warm slightly if you like. The texture holds up surprisingly well.
Pineapple Upside Down Cupcakes are one of those recipes that feel generous. They are easy to make, easy to share, and they carry a little bit of nostalgia in every bite.
Every time I make them, I am reminded why some desserts never go out of style. They just find new ways to show up at the table.
Pineapple Upside Down Cupcakes Recipe
Description
A fun twist on the classic cake, these Pineapple Upside Down Cupcakes deliver all the nostalgic flavor of the original in adorable, individual servings. Each cupcake features a caramelized pineapple slice and maraschino cherry nestled atop a moist yellow cake base—perfect for summer gatherings, BBQs, or holiday desserts.
ingredients
Instructions
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Preheat the oven to 350°F (177°C). Generously spray 24 wells of a muffin tin with cooking spray. Do not use paper liners.
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In a large bowl, combine the reserved pineapple juice (1 cup total), yellow cake mix, vegetable oil, and eggs. Mix until smooth and well blended.
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Cut each pineapple ring into four equal pieces. In a small bowl, mix melted butter and brown sugar until combined.
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Add about 1 teaspoon of the butter-sugar mixture to the bottom of each muffin well. Place two pineapple pieces and one cherry half (cut side up) on top of the mixture in each well.
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Pour the cake batter into each well, filling to about ¼ inch from the top. Bake for 20–25 minutes, or until golden brown and a toothpick inserted in the center comes out clean or with a few moist crumbs.
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Let cupcakes cool in the pan for 15 minutes. Run a knife around the edges to loosen, then carefully invert onto a cooling rack. Serve warm with whipped cream if desired.
Nutrition Facts
Servings 24
- Amount Per Serving
- Calories 210kcal
- % Daily Value *
- Total Fat 9g14%
- Saturated Fat 3g15%
- Cholesterol 25mg9%
- Sodium 210mg9%
- Potassium 85mg3%
- Total Carbohydrate 32g11%
- Sugars 22g
- Protein 2g4%
- Calcium 4 mg
- Iron 6 mg
* Percent Daily Values are based on a 2,000 calorie diet. Your daily value may be higher or lower depending on your calorie needs.
Note
- Pineapple options: Use crushed pineapple, tidbits, or chunks if preferred—but ensure you have 1 cup of juice for the batter.
- Liners: Avoid paper liners—they prevent proper caramelization. Silicone liners or a well-greased pan work best.
- Cake mix swap: Try pineapple-flavored cake mix for an extra tropical punch.
- Flipping tip: Don’t wait too long to invert—cool just enough to handle but while topping is still warm and sticky.
