Try these delicious Pineapple Upside Down Cupcakes for a tropical twist on a classic dessert! Moist yellow cake topped with caramelized pineapple and maraschino cherries. Perfect for parties, gatherings, or a special treat. Easy to make and fun to eat, these cupcakes are a must-try.

Ingredients:
- 1 can (20 oz) sliced pineapple, drained, juice reserved
- 1 box yellow cake mix
- 1/2 cup vegetable oil
- 3 eggs
- 1/3 cup butter, melted
- 2/3 cup packed brown sugar
- 12 maraschino cherries, cut in half
Preparation:
- Prepare the Oven and Muffin Cups: Preheat your oven to 350°F (175°C). Generously spray 24 regular-size muffin cups with cooking spray to ensure easy removal of the cupcakes.
- Prepare the Pineapple: Cut each pineapple slice into 4 pieces and set aside. These will be used to create the signature pineapple topping for each cupcake.
- Mix the Cake Batter: In a large bowl, combine the yellow cake mix, vegetable oil, eggs, and reserved pineapple juice. Beat the mixture with an electric mixer on low speed for 30 seconds to combine, then on medium speed for 2 minutes, scraping the bowl occasionally to ensure a smooth batter.
- Create the Topping: In a small bowl, stir together the melted butter and brown sugar until well combined. Spoon 1 1/2 teaspoons of the butter mixture into the bottom of each prepared muffin cup.
- Add Pineapple and Cherries: Place 2 pieces of pineapple into each muffin cup on top of the butter mixture. Add a maraschino cherry half, cut side up, in the center of the pineapple pieces.
- Fill the Muffin Cups: Spoon about 1/4 cup of the cake batter into each muffin cup, covering the pineapple and cherry pieces.
- Bake the Cupcakes: Bake in the preheated oven for 20 to 25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean. Allow the cupcakes to cool in the pan for 5 minutes.
- Invert and Serve: Run a knife around the edge of each cupcake to loosen it from the pan. Carefully invert the cupcakes onto a cookie sheet. Serve them warm to enjoy the full, gooey goodness of the caramelized pineapple topping.
Why You’ll Love Pineapple Upside Down Cupcakes
Easy and Convenient
These cupcakes are a breeze to make using a box of yellow cake mix and canned pineapple. The individual servings are perfect for parties and make a great presentation.
Tropical Flavor
The combination of caramelized pineapple, brown sugar, and maraschino cherries provides a delicious tropical flavor that pairs beautifully with the moist yellow cake.
Perfect for Any Occasion
Whether it’s a summer barbecue, a birthday party, or just a weeknight dessert, these cupcakes are sure to be a crowd-pleaser. Their vibrant appearance and sweet flavor make them suitable for any celebration.
Tips for the Best Pineapple Upside Down Cupcakes
- Use Fresh Ingredients: For the best flavor, make sure your eggs and butter are fresh.
- Prevent Sticking: Be generous with the cooking spray to ensure the cupcakes release easily from the pan.
- Serve Warm: These cupcakes are best enjoyed warm, allowing the caramelized topping to be gooey and delicious.



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