These Pineapple Upside Down Cupcakes are a fun individual twist on the classic pineapple upside-down cake. Each cupcake has a buttery brown sugar and pineapple topping that caramelizes beautifully while baking, followed by a soft, moist vanilla cake underneath. Once flipped, the pineapple and cherry topping sits right on top, creating a beautiful dessert that is perfect for parties, family gatherings, or an easy weeknight treat.
Ingredients
For the Pineapple Topping
- 1 can (20 oz) pineapple rings or pineapple chunks, drained
- 1/2 cup packed brown sugar
- 1/4 cup unsalted butter, melted
- 12 maraschino cherries
- 1/2 teaspoon vanilla extract
For the Cupcake Batter
- 1 1/2 cups all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/4 teaspoon salt
- 1/2 cup unsalted butter, softened
- 3/4 cup granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 1/2 cup pineapple juice, reserved from the can
- 1/4 cup milk
Instructions
1. Prepare the Oven and Pan
Preheat your oven to 350°F (175°C).
Grease a 12-cup muffin pan generously, making sure to coat the bottoms and sides well. This will make it easier to turn the cupcakes out after baking.
2. Make the Pineapple Topping
In a small bowl, combine the melted butter and brown sugar.
Spoon about 1 tablespoon of the mixture into the bottom of each muffin cup.
Place a pineapple ring or a few small pineapple chunks over the brown sugar mixture. If using pineapple rings, cut them into smaller pieces so they fit comfortably in the muffin cups.
Place one maraschino cherry in the center of each pineapple arrangement.
3. Prepare the Batter
In a medium bowl, whisk together the flour, baking powder, and salt.
In a separate large bowl, beat the softened butter and granulated sugar for about 2–3 minutes, until light and fluffy.
Add the eggs one at a time, beating well after each addition. Mix in the vanilla extract.
Add the dry ingredients gradually, alternating with the pineapple juice and milk. Begin and end with the dry ingredients.
Mix just until the batter is smooth. Avoid overmixing, as this can make the cupcakes dense.
4. Fill the Muffin Cups
Carefully spoon the batter over the pineapple topping, filling each cup about two-thirds full.
Gently smooth the tops with the back of a spoon.
5. Bake
Bake for approximately 20–25 minutes, or until the cupcakes are golden and a toothpick inserted into the cake portion comes out clean.
Allow them to cool in the pan for about 5–10 minutes.
6. Flip the Cupcakes
Run a thin knife around the edges of each cupcake if necessary.
Place a large tray or serving platter over the muffin pan and carefully invert the pan in one quick motion.
Lift the pan away slowly.
The caramelized pineapple and cherry topping should now be beautifully displayed on top of each cupcake.
If any pineapple topping remains in the pan, simply spoon it back onto the cupcakes.
Helpful Tips
- Drain the pineapple well so excess liquid doesn’t make the cupcakes soggy.
- Don’t let the cupcakes cool completely in the pan, because the brown sugar topping can become sticky and difficult to release.
- Grease the muffin pan generously, especially if you’re using a traditional metal pan.
- For extra pineapple flavor, replace some or all of the milk with reserved pineapple juice.
- Don’t overmix the batter. A few gentle strokes are better than beating it excessively.
- If using pineapple chunks instead of rings, arrange them tightly together to create an attractive topping.
Make-Ahead and Storage
Store completely cooled cupcakes in an airtight container at room temperature for up to 2 days, or refrigerate them for up to 4 days.
For the best texture, allow refrigerated cupcakes to come closer to room temperature before serving.
Final Thoughts
These Pineapple Upside Down Cupcakes combine everything people love about the classic dessert in a convenient individual serving. The caramelized brown sugar, juicy pineapple, bright cherry, and tender vanilla cake come together in every bite for a sweet and nostalgic treat that’s as pretty as it is delicious.