Last updated: October 31, 2026
Pineapple upside down cupcakes give you everything people love about the classic cake in a handheld size, with a sticky brown sugar top, a juicy pineapple ring, and a tender buttery crumb. This batch makes 12, bakes in a standard muffin tin, and the full recipe card is below.
What You Need for Pineapple Upside Down Cupcakes
Pineapple upside down cupcakes come together in two parts: a sticky topping that goes in the bottom of the pan and a simple buttery batter that goes on top. Everything comes from the pantry and the canned fruit aisle, and you need about 20 minutes of prep, 22 minutes in the oven, and a 5 minute rest before flipping.
The Topping
The topping is 1/4 cup of melted unsalted butter stirred together with 1/2 cup of packed light brown sugar. Light brown sugar gives a clean caramel flavor, while dark brown sugar makes the topping deeper and a little more molasses forward.
Each cupcake gets one half ring of canned pineapple and one maraschino cherry. You need 6 rings from a 20 ounce can of pineapple rings packed in juice, cut in half to make 12 pieces, plus 12 cherries with the stems removed.
The Batter
The batter starts with 1 1/2 cups (190 g) of all-purpose flour, 1 1/2 teaspoons of baking powder, and 1/4 teaspoon of salt. It also takes 1/2 cup (113 g) of softened unsalted butter, 3/4 cup (150 g) of granulated sugar, 2 large room temperature eggs, and 1 teaspoon of vanilla extract.
The liquid is 1/4 cup of whole milk and 1/4 cup of the juice from the pineapple can. Using juice for half of the liquid is the small detail that makes the crumb taste like pineapple instead of plain vanilla cake.
The Equipment
You need one standard 12-cup muffin tin, a small bowl for the topping, a mixing bowl, and a baking sheet or wire rack for flipping. Skip paper liners, because the topping has to turn out onto the rack along with the cake.
Measure the flour by weight if you can. Scooping straight from the bag packs in extra flour and makes the cupcakes dry.
How to Make Pineapple Upside Down Cupcakes Step by Step
The method is topping first, batter second, then a quick bake and a flip. Preheat the oven to 350°F before you start, and grease every cup and the flat top of the pan generously with butter or nonstick spray.
Build the Topping
Drain the pineapple over a bowl and keep 1/4 cup of the juice for the batter. Pat the rings dry with a paper towel, then cut 6 of them in half to make 12 half rings.
Melt 1/4 cup of butter, stir in the brown sugar until smooth, and spoon about 1 tablespoon into each cup. Set one half ring in each cup with a cherry tucked into the curve.
Mix the Batter
Whisk the flour, baking powder, and salt together in a bowl. In a second bowl, beat the softened butter and granulated sugar for 2 minutes, until the mixture looks pale and fluffy.
Beat in the eggs one at a time, then the vanilla. Stir the milk and pineapple juice together, then add the flour mixture in three parts and the liquid in two parts, starting and ending with flour.
Fill and Bake
Fill each cup about two-thirds full, which is roughly 3 heaping tablespoons of batter. Spread it gently over the fruit so the pineapple stays put.
Bake for 20 to 22 minutes, until the tops are golden and a toothpick in the center comes out clean. Every oven runs a little different, so start checking at 20 minutes.
Flip and Serve
Cool the pan on a wire rack for exactly 5 minutes, then run a thin knife around each cupcake. Set a baking sheet over the pan, flip both together, and lift the pan away.
Spoon any caramel left behind in the cups back over the tops. Serve the cupcakes warm or at room temperature.
Tips for Pineapple Upside Down Cupcakes That Release Clean
The most common problem with pineapple upside down cupcakes is a topping that stays behind in the pan. Almost every sticking problem comes down to greasing, timing, or moisture, and all three are easy to control.
Grease Like You Mean It
Brown sugar caramel grips metal as it cools, so a thin film of butter is not enough. Brush or spray every cup, including the flat top of the pan, so any caramel that bubbles over does not weld the tin shut.
Respect the 5 Minute Rest
Five minutes is the window that works. If you flip right out of the oven the caramel is too runny and slides off the fruit, and if you wait much longer it cools and glues the cupcakes to the pan.
If a pineapple piece does stick, lift it out with a spoon and press it back onto its cupcake. The warm caramel hides the repair completely.
Dry the Pineapple
Wet pineapple waters down the caramel and makes the topping slide. Blot the rings on a paper towel before cutting them, and shake off any extra juice from the cherries too.
Do Not Overmix
Once the flour goes in, mix only until you no longer see dry streaks. Extra mixing builds gluten, which makes the crumb tough instead of tender.
Room temperature eggs and butter blend smoothly with very little effort. Cold eggs can make the creamed butter look curdled and the batter heavy.
Variations and Substitutions
The recipe is forgiving, and a few swaps change the flavor without changing the method. Stick to the same amounts in the card and the bake time stays the same.
Fresh Pineapple
Fresh pineapple works if you slice it thin, about 1/4 inch, and pat it dry. Fresh fruit has no can juice, so use 1/4 cup of bottled pineapple juice in the batter instead.
Buttermilk or Dark Brown Sugar
Swap the 1/4 cup of whole milk for 1/4 cup of buttermilk if you like a slightly tangy crumb. Dark brown sugar in the topping gives a deeper, more molasses flavor.
No Cherries
The card lists cherries because they give the classic look, but they are optional. Leave them out and the cupcakes taste just as good, with a plain pineapple top.
Coconut Topping
Toasted coconut flakes sprinkled over the flipped cupcakes add crunch and a tropical flavor. Add them right after flipping so they stick to the warm caramel.
Storing, Freezing, and Serving Pineapple Upside Down Cupcakes
Store the cooled cupcakes covered at room temperature for up to 1 day, then move them to the refrigerator for up to 4 days. Warm a cold cupcake in the microwave for 10 to 15 seconds so the caramel softens again.
For longer storage, wrap each cupcake individually and freeze them for up to 2 months. Thaw them overnight in the refrigerator, then warm briefly before serving.
These are best warm with a scoop of vanilla ice cream or a spoonful of softly whipped cream. They also travel well, which makes them a good choice for potlucks, bake sales, and holiday dessert tables.
The Story Behind Pineapple Upside Down Cake
Upside down cakes were baked in cast iron skillets long before canned pineapple existed, with fruit and sugar on the bottom and batter poured over the top. The pineapple version took off in the early 1900s once canned rings were sold in American grocery stores.
The Hawaiian Pineapple Company, later known as Dole, helped make the cake famous by promoting recipes that used its canned fruit. Cupcakes are the modern, portion-friendly take, and they bake faster than a full cake.
Ready to bake? Use the recipe card below for the full ingredient list, step by step method, and nutrition information.
Pineapple Upside Down Cupcakes
Sticky brown sugar tops, juicy pineapple, and a tender buttery crumb in an easy muffin tin cupcake that flips out clean.
Ingredients
- 1/4 cup (57 g) unsalted butter, melted
- 1/2 cup (100 g) packed light brown sugar
- 1 can (20 ounces) pineapple rings in juice, drained, 1/4 cup juice reserved
- 12 maraschino cherries, stems removed, patted dry
- 1 1/2 cups (190 g) all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/4 teaspoon salt
- 1/2 cup (113 g) unsalted butter, softened
- 3/4 cup (150 g) granulated sugar
- 2 large eggs, room temperature
- 1 teaspoon vanilla extract
- 1/4 cup whole milk
- 1/4 cup reserved pineapple juice
Instructions
- Preheat the oven to 350°F. Generously grease a 12-cup standard muffin tin, including the flat top of the pan, with butter or nonstick spray. Do not use liners.
- Drain the pineapple over a bowl and reserve 1/4 cup of the juice. Pat the rings dry with a paper towel and cut 6 of them in half to make 12 half rings.
- Melt 1/4 cup butter and stir in the brown sugar until smooth. Spoon about 1 tablespoon into each muffin cup.
- Set one pineapple half ring in each cup and tuck a maraschino cherry into the curve.
- In a bowl, whisk together the flour, baking powder, and salt.
- In a large bowl, beat the softened butter and granulated sugar for 2 minutes, until pale and fluffy.
- Beat in the eggs one at a time, then the vanilla.
- Stir the milk and the reserved pineapple juice together. Add the flour mixture in three parts and the milk mixture in two parts, starting and ending with flour. Mix only until no dry streaks remain.
- Fill each cup about two-thirds full, about 3 heaping tablespoons of batter, and gently spread it over the fruit.
- Bake for 20 to 22 minutes, until the tops are golden and a toothpick in the center comes out clean.
- Cool the pan on a wire rack for exactly 5 minutes, then run a thin knife around each cupcake.
- Place a baking sheet over the pan, flip both together, and lift the pan away. Spoon any caramel left in the cups over the tops. Serve warm or at room temperature.
Notes
Skip paper liners so the topping turns out with the cake. Maraschino cherries are optional. Store covered at room temperature for up to 1 day, then in the refrigerator for up to 4 days. Freeze individually wrapped for up to 2 months and thaw overnight in the refrigerator. Warm for 10 to 15 seconds in the microwave before serving.
Nutrition Information:
Yield:
12Serving Size:
1 cupcakeAmount Per Serving: Calories: 270Total Fat: 12gSaturated Fat: 8gSodium: 125mgCarbohydrates: 37gFiber: 1gSugar: 24gProtein: 3g
Pineapple Upside Down Cupcakes FAQ
Can you use fresh pineapple instead of canned?
Yes, as long as you slice it about 1/4 inch thick and pat it dry. Use 1/4 cup of bottled pineapple juice in the batter, since fresh fruit does not come with can juice.
Why did my topping stick to the pan?
Sticking usually means the pan was under-greased or the cupcakes sat too long before flipping. Grease every cup and the flat top of the pan, and flip after exactly 5 minutes of cooling.
Can you use cupcake liners?
Liners are not a good fit here because the caramel topping needs to turn out onto the rack with the cake. A well-greased metal tin releases the cupcakes cleanly without them.
Can you make these ahead of time?
Yes. Store them covered at room temperature for up to 1 day or in the refrigerator for up to 4 days, and freeze them individually wrapped for up to 2 months.
Do you have to use maraschino cherries?
No, they are optional. They add the classic look, but the cupcakes taste the same without them.
Why This Recipe Works
Beating the butter and granulated sugar together for 2 minutes traps tiny air bubbles in the batter. Those bubbles, along with 1 1/2 teaspoons of baking powder, give the cupcakes a soft, even rise without a dense center.
Adding the eggs one at a time keeps the batter smooth instead of curdled, and alternating the flour with the milk and pineapple juice means you never overmix. The result is a tender, buttery crumb with real pineapple flavor in every bite.
The topping does its own work in the oven. Melted butter and brown sugar turn into a sticky caramel under the fruit, and filling the cups only two-thirds full leaves room for the cake to rise without pushing that caramel up the sides.
Make Pineapple Upside Down Cupcakes Tonight
Pineapple upside down cupcakes are an easy way to turn a can of pineapple and a few pantry staples into something that looks bakery made. Preheat the oven, grease the pan well, and bake a batch of 12 today.
If you make them, leave a rating and a comment below so we know how they turned out. Save the recipe to your Pinterest dessert board so you can find it again next time a craving hits.
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