Description
These Pineapple Upside-Down Cupcakes feature moist, buttery cake topped with caramelized brown sugar, pineapple rings, and optional maraschino cherries for a classic retro dessert in convenient individual portions. Perfect for parties or a sweet treat, these cupcakes combine the tropical tang of pineapple with a rich, fluffy cake base.
Ingredients
Scale
Topping
- 1 can (20 oz) pineapple rings, drained
- 1/4 cup unsalted butter, melted
- 1/4 cup packed brown sugar
- Maraschino cherries (optional, for garnish)
Cake Batter
- 1 1/2 cups all-purpose flour
- 1 1/2 tsp baking powder
- 1/4 tsp salt
- 1/2 cup unsalted butter, softened
- 3/4 cup granulated sugar
- 2 large eggs
- 1 tsp vanilla extract
- 1/2 cup whole milk
Instructions
- Preheat and prepare muffin tin. Preheat your oven to 350°F (175°C). Grease a 12-cup muffin tin or line with paper cupcake liners to prevent sticking.
- Make the caramel topping. In a small bowl, melt the butter and stir in the brown sugar until combined. Spoon this mixture evenly into the bottom of each muffin cup.
- Add pineapple and cherries. Place one pineapple ring in the center of each muffin cup atop the brown sugar mixture. If needed, cut rings into smaller pieces to fit. Add a maraschino cherry in the center of each pineapple ring if desired.
- Mix dry ingredients. In a separate bowl, whisk together the all-purpose flour, baking powder, and salt for the cake batter.
- Cream butter and sugar. In a large bowl, beat the softened butter and granulated sugar until light and fluffy. Add the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
- Combine wet and dry ingredients. Gradually add the flour mixture to the wet ingredients, alternating with the milk. Start and end with the flour mixture. Mix just until combined to avoid overmixing.
- Fill muffin cups. Spoon the cake batter over the pineapple and brown sugar mixture, filling each muffin cup about two-thirds full.
- Bake cupcakes. Bake in the preheated oven for 20-25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
- Cool and invert. Let the cupcakes cool in the tin for 5 minutes. Run a knife around the edges to loosen, then carefully invert the tin onto a serving platter to release the cupcakes with the pineapple topping displayed on top.
- Serve. Serve the pineapple upside-down cupcakes warm or at room temperature for best flavor and texture.
Notes
- You can use fresh pineapple slices instead of canned if preferred; just adjust draining time.
- For extra moisture, brush the tops with reserved pineapple juice.
- Maraschino cherries are optional but add a lovely pop of color and sweetness.
- Ensure to gently mix the batter to keep cupcakes tender and fluffy.
- If not serving immediately, store cupcakes upright in an airtight container at room temperature for up to 2 days.
