These Pineapple Upside-Down Cupcakes are a tropical twist on a classic dessert, delivering a burst of sweet, tangy flavor in every bite. The golden caramelized pineapple crowns a moist, buttery cake, creating a perfect balance of textures. With just 50 minutes from start to finish, they’re an effortless way to impress guests or satisfy your sweet tooth. Each cupcake is a mini masterpiece, combining the richness of caramel with the freshness of fruit for a treat that feels indulgent yet light.
Warm, gooey pineapple pairs beautifully with the tender crumb of the cake, while a hint of vanilla adds a comforting aroma. These cupcakes are not only visually stunning but also packed with vitamin C and a touch of tropical sunshine. Whether for a party or a cozy afternoon, they’re sure to bring smiles and compliments. Plus, their individual servings make them ideal for sharing—or keeping all to yourself!
Ingredients for Pineapple Upside-Down Cupcakes
- For the topping:
- 6 Tablespoons (85 g) salted butter, melted
- 12 Tablespoons (150 g) light brown sugar, firmly packed (approx. ¾ cup)
- 2 ⅓ cups (438 g) pineapple chunks, drained and patted dry (canned or fresh)
- 12 Maraschino cherries, drained
- For the cupcakes:
- ½ cup (113 g) unsalted butter, softened to room temperature
- ¾ cup (150 g) granulated sugar
- 2 large eggs, room temperature preferred
- 1 teaspoon vanilla extract
- 1 ½ cups (187 g) all-purpose flour
- 1 ½ teaspoons baking powder
- ¼ teaspoon table salt
- ½ cup (118 ml) buttermilk (or substitute with ½ cup milk + ½ teaspoon lemon juice)
Step-by-Step Instructions
- Preheat the oven: Set it to 350°F (175°C).
- Prepare the topping: Evenly divide the melted salted butter into the bottom of each cupcake well, and lightly brush the sides with butter using a pastry brush.
- Add the sugar: Sprinkle 1 Tablespoon (12 g) of light brown sugar evenly into the bottom of each cupcake well.
- Arrange pineapple and cherries: Place 4 pineapple chunks in a flower pattern over the butter and sugar. Press a Maraschino cherry into the center of each “flower.” Set aside.
- Make the cupcake batter: In a mixing bowl, beat the softened unsalted butter and granulated sugar together until light and fluffy.
- Add wet ingredients: Beat in the eggs and vanilla extract until well combined.
- Combine dry ingredients: In a separate bowl, whisk together the flour, baking powder, and salt.
- Mix batter: Alternate adding the flour mixture and buttermilk to the butter mixture, starting and ending with the flour. Stir gently with a spatula until just combined (avoid over-mixing).
- Fill the pan: Evenly divide the batter into the prepared cupcake wells, filling to the rim (discard any excess). Gently spread the thick batter with a spoon.
- Bake: Place the cupcake tin on a foil-lined rimmed baking sheet (to catch spills) and bake on the center rack for 22-25 minutes. A toothpick inserted in the center should come out clean or with moist crumbs.
- Cool: Let the cupcakes cool in the pan for 5 minutes. Use a knife to gently loosen the edges, then invert onto a wire cooling rack. Carefully lift the tin to release the cupcakes.
- Serve: Allow to cool slightly. Enjoy warm, optionally with a scoop of vanilla ice cream!
Sweet Serving Suggestions
These Pineapple Upside-Down Cupcakes are delicious on their own, but they truly shine with a scoop of vanilla ice cream or a dollop of whipped cream. For a tropical twist, drizzle with caramel sauce or sprinkle with toasted coconut flakes. They’re perfect for dessert, brunch, or even a sweet snack!
Storage and Reheating Tips
Store leftover cupcakes in an airtight container at room temperature for up to 2 days or in the fridge for up to 5 days. To reheat, warm them in the microwave for 10-15 seconds or in a 300°F (150°C) oven for 5 minutes. Pro tip: Let them cool slightly before serving to avoid burning your mouth!
Recipe Variations to Try
Switch things up by using canned peach slices or mandarin oranges instead of pineapple. For a nutty flavor, sprinkle chopped pecans over the brown sugar layer. If you’re feeling adventurous, add a splash of rum or coconut extract to the batter for a boozy or tropical twist!
Time-Saving Hacks
To speed up prep, use a pre-measured cupcake pan to evenly distribute the butter and sugar. If you don’t have buttermilk, make a quick substitute by mixing ½ cup milk with ½ teaspoon lemon juice and letting it sit for 5 minutes. Pre-drained pineapple chunks also save time—just pat them dry before using!
Equipment Guidance
A non-stick cupcake pan is essential for easy release, but if you don’t have one, generously grease your pan with butter. Use a pastry brush to evenly coat the sides with butter and a small offset spatula to spread the batter smoothly. A rimmed baking sheet underneath prevents spills and makes cleanup a breeze!
Pineapple Upside-Down Cupcakes
Ingredients
For the topping
- 6 Tablespoons salted butter melted
- 12 Tablespoons light brown sugar firmly packed (¾ cup)
- 2 ⅓ cups pineapple chunks drained/patted dry (see note)
- 12 Maraschino cherries drained
For the cupcakes
- ½ cup unsalted butter softened to room temperature
- ¾ cup granulated sugar
- 2 large eggs room temperature preferred
- 1 teaspoon vanilla extract
- 1 ½ cups all-purpose flour
- 1 ½ teaspoons baking powder
- ¼ teaspoon table salt
- ½ cup buttermilk
Instructions
- Preheat oven to 350F (175C). Evenly divide butter into the bottom of each cupcake well and use a pastry brush to lightly brush the sides with butter as well.
- Sprinkle 1 Tablespoon (12 grams) of sugar evenly into the bottom of each cupcake well.
- Arrange 4 pineapple chunks in a flower pattern over the butter and brown sugar and press a Maraschino cherry into the center of each “flower”. Set aside as you prepare your cupcake batter.
- For the cupcakes: Combine butter and sugar in a medium-sized mixing bowl (or the bowl of a stand mixer fitted with the paddle attachment) and use an electric mixer to beat until light and fluffy.
- Add eggs and vanilla extract and beat well.
- In a separate mixing bowl, whisk together flour, baking powder and salt.
- Alternate adding the flour mixture and the buttermilk to the batter, starting and ending with the flour mixture and stirring until just combined after each addition (I add the flour mixture in 4 parts and the buttermilk in 3 parts and recommend doing this part gently by hand with a spatula to not over-mix).
- Evenly divide the cupcake batter into your prepared pan, filling each cupcake well to the rim (don’t overfill, if you have excess batter discard it). The batter will be thick, so use a spoon to gently spread it into each cupcake well.
- Place cupcake tin on a foil lined rimmed baking sheet (in case of spills) and transfer to center rack of 350F (175C) preheated oven and bake for 22-25 minutes and a toothpick inserted in the center comes out clean or with moist crumbs.
- Allow cupcakes to cool in pan for 5 minutes then use a knife to gently loosen the cupcake from the edges of the pan before inverting. Place a wire cooling rack over the cupcake tin and, carefully, using potholders (the tin will be very hot!) keep the cooling rack pressed securely against the tin and invert cupcakes onto cooling rack. Lift the tin, the cupcakes should release easily.
- Allow to cool a bit before serving. These are great served warm and we love them with vanilla ice cream, too!