Pineapple upside down cupcakes have a way of pulling people into the kitchen without trying too hard. They feel familiar, a little nostalgic, and somehow cheerful even before they’re baked. For me, they land right in that sweet spot between classic comfort and everyday baking.
I grew up eating the full-sized cake version, usually at family gatherings where it disappeared faster than anyone expected. Turning it into cupcakes just makes sense. No slicing, no worrying about cracks, and everyone gets their own perfectly topped little dessert.
What I love most is..
how forgiving these are. The caramel sauce keeps the cake moist, the pineapple adds brightness, and the whole thing feels special without being fussy. They look impressive, but the process stays relaxed and approachable.
These cupcakes are also crowd-friendly in the best way. They travel well, they don’t need frosting, and they’re sturdy enough to sit out at a party without losing their charm. Birthdays, potlucks, BBQs, they fit right in.
Ingredients Needed for the Recipe
- Pineapple slices – These form the signature topping and bring sweetness and moisture.
- Maraschino cherries – Tucked into the center for color and a pop of classic flavor.
- Brown sugar – Creates that rich caramel layer once baked and flipped.
- Melted butter – Helps the sugar melt smoothly and prevents sticking.
- All-purpose flour – The base structure of the cupcakes.
- White sugar – Sweetens the cake without overpowering the fruit.
- Baking powder – Gives the cupcakes their lift.
- Salt – Balances the sweetness and sharpens flavors.
- Softened butter – Adds richness and keeps the crumb tender.
- Vanilla – Rounds out the flavors with warmth.
- Eggs – Bind everything together and add structure.
- Milk – Keeps the batter smooth and the cake moist.
One small thing I’ve learned is to prep the pineapple carefully. Draining and patting it dry sounds minor, but it makes a noticeable difference. Too much liquid can throw off the texture and the caramel layer.
I also stick with canned pineapple here. Fresh pineapple releases extra juice as it bakes, and that can make the cupcakes soggy. This is one of those moments where canned really is the better choice.
How to make Pineapple Upside Down Cupcakes?
Step 1 – Prepare the pan
Start by preheating the oven to 350 degrees F. Generously spray your muffin pan with nonstick baking spray, making sure to coat the bottoms well since that’s where the topping will sit.
Skipping liners is important here. These cupcakes need to be flipped, and liners can cause sticking or tearing. A well-greased pan does the job much better.
Step 2 – Build the topping
In a bowl, mix the brown sugar with the melted butter until it looks glossy and smooth. Spoon the mixture evenly into each muffin cup, spreading it gently across the bottom.
Place a pineapple slice on top of the sugar mixture, then press a cherry into the center. It doesn’t have to be perfect, everything settles as it bakes.
Step 3 – Mix the dry ingredients
In a separate bowl, whisk together the flour, baking powder, and salt. This quick step helps everything distribute evenly and prevents pockets of bitterness or uneven rise.
I always take a second to level my flour properly. Scooping directly from the bag packs it down, and that’s an easy way to end up with dense cupcakes.
Step 4 – Cream the butter and sugar
In a large bowl, beat the softened butter with the white sugar until light and fluffy. This step builds air into the batter, which helps keep the cupcakes tender.
Add the vanilla, then beat in the eggs one at a time. Let each egg fully mix in before adding the next, scraping down the sides as needed.
Step 5 – Combine wet and dry
Alternate adding the flour mixture and the milk to the butter mixture. Start and end with the dry ingredients, mixing just until everything comes together.
This is where restraint matters. Overmixing can make the cupcakes tough, and there’s no benefit to pushing it once the batter looks smooth.
Step 6 – Fill and bake
Spoon the batter over the pineapple layers, filling each cup about two-thirds full. The cupcakes will rise, so leaving space prevents overflow.
Bake for 18 to 22 minutes, until a toothpick inserted in the center comes out with a few moist crumbs. Let them cool briefly before flipping.
Tips
- Don’t overmix the batter, stop as soon as it’s combined.
- Drain and pat the pineapple dry to avoid excess moisture.
- Use softened butter, not melted, for the cake batter.
- Flip the cupcakes 5 to 10 minutes after baking for best release.
- If one sticks, gently loosen the edge with a butter knife.
Flipping can feel intimidating the first time, but it gets easier fast. I like placing a baking sheet over the pan, then turning everything over in one confident motion.
If a cupcake doesn’t drop immediately, patience helps. Gravity usually does the work after a few seconds, and forcing it can ruin the topping.
Why these cupcakes work so well
The balance here is what keeps me coming back to this recipe. The cake itself is soft and lightly sweet, letting the caramelized fruit shine without feeling heavy.
Because each cupcake has its own topping, every bite gets that perfect mix of cake, pineapple, and caramel. There’s no fighting for the best slice.
They also stay moist longer than most cupcakes. The brown sugar syrup and fruit lock in moisture, so leftovers still taste great the next day.
Serving ideas that feel effortless
These cupcakes are lovely on their own, but a little extra never hurts. A spoonful of whipped cream adds softness without overpowering the flavors.
Vanilla ice cream is another favorite here, especially if the cupcakes are slightly warm. The contrast between cold and caramelized fruit is hard to beat.
For casual gatherings, I serve them straight from the baking sheet. They don’t need fancy plating to feel special, and that’s part of their charm.
Storage and make-ahead notes
If you’re planning ahead, these can be made a day in advance. Once cooled, store them in an airtight container at room temperature.
I avoid refrigerating unless absolutely necessary. The cold can firm up the cake and dull the flavors, which takes away from their appeal.
If you do need to chill them, let them come back to room temperature before serving. They soften up nicely with a little time.
Pineapple Upside Down Cupcakes Recipe
Description
These Pineapple Upside-Down Cupcakes feature moist vanilla cake topped with a rich caramelized brown sugar sauce and juicy pineapple slices crowned with maraschino cherries. A nostalgic twist on the classic dessert, these cupcakes are perfect for parties, potlucks, or anytime you're craving a tropical treat!
ingredients
For the Topping
For the Cakes
Instructions
-
Preheat oven to 350°F (175°C). Spray a standard 12-cup muffin tin (or mini Bundt pan) with non-stick baking spray. Do not use cupcake liners.
-
In a small bowl, mix melted butter and brown sugar. Divide evenly among the bottoms of the muffin cups (about 1 tablespoon per cup). Place one pineapple slice in each cup and top with a maraschino cherry.
-
In a medium bowl, whisk together flour, baking powder, and salt.
-
In a large bowl, cream softened butter and granulated sugar until light and fluffy. Add vanilla and eggs one at a time, mixing well after each addition.
-
Alternate adding the flour mixture and milk to the butter mixture, beginning and ending with the flour. Mix just until combined—do not overmix.
-
Divide batter evenly over the pineapple-cherry topping in each cup (fill about â…” full).
-
Bake for 18–22 minutes, or until a toothpick inserted in the center comes out with a few moist crumbs.
-
Let cool in the pan for 5–10 minutes, then carefully invert onto a wire rack or baking sheet to cool completely.
Nutrition Facts
Servings 12
Serving Size 1 cupcake
- Amount Per Serving
- Calories 320kcal
- % Daily Value *
- Total Fat 13gg20%
- Saturated Fat 8gg40%
- Trans Fat 0gg
- Cholesterol 75mgmg25%
- Sodium 220mgmg10%
- Potassium 180mgmg6%
- Total Carbohydrate 48gg16%
- Dietary Fiber 1gg4%
- Sugars 34gg
- Protein 4gg8%
- Calcium 8 mg
- Iron 8 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
- Flour Tip: Spoon flour into measuring cup and level off—don’t scoop directly from the bag.
- Pineapple Prep: Drain thoroughly and pat dry to avoid excess moisture in the cupcakes.
- No Liners: Do not use paper liners—they prevent proper flipping and caramel release.
- Storage: Store cooled cupcakes in an airtight container at room temp for up to 2 days or refrigerate for up to 5 days.
Frequently Asked Questions
Can I make these ahead of time?
Yes! These cupcakes taste great the next day. Store them covered at room temperature for up to 2 days or refrigerate for longer freshness.
Can I use fresh pineapple instead of canned?
It’s not recommended—fresh pineapple contains more moisture and enzymes that can affect texture and browning. Canned pineapple (in juice, not syrup) works best.