Pineapple upside down cupcakes are a tropical twist on the classic dessert, delivering sunny flavor in every bite-sized portion. Perfectly sweet, buttery, and vibrant, they’re a nostalgic treat made easy.
With caramelized pineapple, golden cake, and a pop of cherry on top, these cupcakes bring retro charm to modern gatherings. They’re quick to make, irresistibly cute, and always a crowd-pleaser.
Sweet Essentials for Pineapple Upside Down Cupcakes
- Pineapple rings – Juicy and tangy, these form the signature base (or top!) of the upside down design, adding tropical flavor and moisture.
- Yellow cake mix – A quick and fluffy shortcut that provides the perfect golden sponge to cradle the fruity topping.
- Brown sugar – Rich and molasses-kissed, it caramelizes in the oven to create that iconic sticky-sweet topping.
- Butter – Melted into the brown sugar, it adds richness and helps form that luscious, syrupy bottom.
- Maraschino cherries – Bright, festive, and sweet, they complete the iconic look and provide a burst of color and flavor.
- Eggs and vegetable oil – These bind and enrich the cake batter, ensuring tender and moist cupcakes.
- Reserved pineapple juice – Replaces water in the cake mix, amplifying the pineapple flavor in every bite.
How to Make Pineapple Upside Down Cupcakes
Start by preheating your oven and prepping your muffin tin with non-stick spray.
Whisk together the cake mix, reserved pineapple juice, oil, and eggs until smooth and well combined.
Stir melted butter and brown sugar together, then spoon into each muffin well. Arrange two pineapple pieces and half a cherry in each, forming the base layer.
Carefully pour the batter over the fruit, filling each well nearly to the top. Bake until golden and springy to the touch.
Let the cupcakes cool slightly, then gently loosen and flip them onto a cooling rack to reveal their glossy, caramelized tops.
Sweet Success Tips & Fun Twists
Use pineapple tidbits if you prefer a more evenly distributed fruit texture throughout the cupcake. For extra indulgence, try adding a splash of rum extract to the batter for a piña colada-inspired spin.
Letting the cupcakes cool for at least 10–15 minutes before inverting is key—this allows the caramelized sugar to set slightly while still being warm enough to release cleanly.
If you’re baking for a special occasion, serve with a swirl of whipped cream or a scoop of coconut ice cream to elevate these charming little cakes into a plated dessert.
Keeping Them Sweet Later: Storing Tips
Pineapple upside down cupcakes can be stored in an airtight container at room temperature for up to two days. For longer freshness, refrigerate them, especially in warmer weather, to keep the fruit topping from spoiling.
If freezing, wrap each cupcake individually to preserve texture and flavor. Thaw overnight in the fridge and bring to room temperature before serving—or give a quick warm-up in the microwave to reawaken that caramel goodness.
Pineapple Upside Down Cupcakes
Ingredients
- ½ cup vegetable oil
- 12 maraschino cherries halved
- ⅓ cup butter melted
- 1 20-ounce can pineapple rings, drained, juice reserved
- 3 eggs
- ⅔ cup packed brown sugar
- 1 15.25-ounce box yellow cake mix
Instructions
- Preheat your oven to 350°F and grease 24 wells of a muffin tin with non-stick spray. In a mixing bowl, combine the reserved pineapple juice with the yellow cake mix, oil, and eggs, stirring until the batter is smooth and fully incorporated. Slice each pineapple ring into four equal parts. Stir together the melted butter and brown sugar, then spoon approximately 1 teaspoon of this mixture into the base of each muffin well. Place two pineapple segments into each well, followed by a cherry half, cut side facing upward. Fill each well with cake batter, leaving about a ¼-inch space from the rim. Bake for 20 to 25 minutes until the tops are golden. After baking, let the cupcakes cool in the pan for 15 minutes. Carefully run a knife around each to loosen and invert them onto a wire rack to finish cooling.
