These Pineapple Upside-Down Cupcakes are a delightful twist on the classic dessert, offering perfectly portioned servings of moist cake topped with caramelized pineapple and cherries. They’re quick to make, fun to serve, and guaranteed to impress at any gathering. A sweet blend of tropical flavors and buttery goodness makes these mini treats irresistible!

Necessary Kitchen Equipment

Muffin tin (12 cups)
Mixing bowls
Whisk or electric hand mixer
Measuring cups and spoons
Non-stick cooking spray

Ingredients

For the Topping:

¼ cup unsalted butter, melted
½ cup packed brown sugar
12 pineapple slices, cut to fit muffin cups
12 maraschino cherries, drained

For the Cake Batter:

1½ cups all-purpose flour
1 cup granulated sugar
2 tsp baking powder
½ tsp salt
½ cup unsalted butter, softened
½ cup pineapple juice (from the canned pineapple)
2 large eggs
1 tsp vanilla extract

Step-by-Step Instructions

Prepare the Muffin Tin:

Preheat your oven to 350°F (175°C). Spray the muffin tin with non-stick cooking spray.
Divide the melted butter evenly among the 12 muffin cups. Sprinkle brown sugar evenly over the butter.
Place a piece of pineapple in each cup, ensuring it fits the bottom. Add a maraschino cherry to the center of each pineapple slice.

Make the Cake Batter:

In a mixing bowl, combine the flour, sugar, baking powder, and salt. Mix well.
Add the softened butter, pineapple juice, eggs, and vanilla extract. Beat with an electric mixer on medium speed until smooth and well combined, about 2 minutes.

Assemble the Cupcakes:

Spoon the batter evenly over the prepared pineapple topping, filling each cup about two-thirds full.

Bake the 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 about 5 minutes. Run a knife around the edges of each cup to loosen them. Place a baking sheet or tray over the muffin tin and carefully invert the cupcakes onto the tray.

Serve:

Allow to cool slightly before serving. These cupcakes are best enjoyed warm or at room temperature.

Recipe Tips

Don’t Overfill the Cups: Avoid overfilling the cups with batter to prevent spillage during baking.
Customize the Topping: Use crushed pineapple or skip the cherries for a variation.
Storage: Store leftovers in an airtight container in the refrigerator for up to 3 days.

What to Serve with Pineapple Upside-Down Cupcakes

Serve with a dollop of whipped cream or a scoop of vanilla ice cream for an extra indulgent treat.

Frequently Asked Questions

1. Can I use fresh pineapple instead of canned?
Yes, fresh pineapple works beautifully, but ensure the slices are thin enough to fit the muffin cups.

2. How do I prevent sticking?
Using non-stick spray and ensuring the topping is well-coated with butter and sugar helps prevent sticking.

3. Can I make these ahead of time?
Yes! Bake the cupcakes and store them in the refrigerator. Reheat gently before serving to restore their fresh flavor.

These Pineapple Upside-Down Cupcakes are a fun, portable take on a classic dessert that’s perfect for parties and special occasions!