Pineapple Upside Down Cupcakes

1. Preheat and Prep
Preheat your oven to 350°F (175°C). Line a muffin tin with paper liners or grease it lightly.
Drain the canned pineapple slices, reserving 1/4 cup of the juice for the batter. Cut the pineapple slices into smaller rounds to fit the bottom of each cupcake liner.
2. Make the Topping
In a small bowl, stir together the melted butter and brown sugar until combined.
Spoon about 1 teaspoon of the brown sugar mixture into the bottom of each cupcake liner, spreading it evenly.
Place a small pineapple round in the center of each liner. Add a maraschino cherry in the middle of the pineapple slice if desired.
3. Prepare the Cupcake Batter
In a large mixing bowl, combine the cake mix, reserved pineapple juice, vegetable oil, eggs, and vanilla extract.
Beat with a hand mixer or whisk until smooth and well combined (about 2 minutes).

4. Assemble the Cupcakes
Spoon the batter gently over the pineapple slices, filling each liner about 2/3 full.
Be careful not to disturb the pineapple topping.
5. Bake the Cupcakes
Bake for 18–22 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
Remove from the oven and let cool in the pan for 5 minutes.
6. Flip and Serve
Carefully flip each cupcake onto a cooling rack or plate, revealing the caramelized pineapple topping.
Let cool completely before serving.
Serving Suggestions
For Dessert: Serve with a dollop of whipped cream or a scoop of vanilla ice cream for extra indulgence.
At Gatherings: Arrange on a platter for potlucks, parties, or holiday celebrations—they’re always a hit!
With Coffee or Tea: Pair with a hot drink for an afternoon treat.
Meal Prep: Store in an airtight container at room temperature for up to 2 days or refrigerate for longer storage.
Pro Tips for Success
Use Fresh Pineapple (Optional): If you have fresh pineapple, slice it thinly and use it in place of canned slices.
Don’t Skip the Cherry: The pop of red from the maraschino cherry adds a festive touch.
Make Mini Cupcakes: Use a mini muffin tin for bite-sized versions—just reduce the baking time to 10–12 minutes.
Enhance the Flavor: Add a splash of rum or coconut extract to the batter for a tropical twist.
Final Thoughts
These Pineapple Upside Down Cupcakes are a sweet, tropical treat that’s perfect for any occasion. With their gooey caramelized topping, tender cake, and juicy pineapple, they’re a dessert that’s as fun to make as they are to eat.

So grab your pineapple slices, melt that butter, and bake up these adorable, fruity cupcakes. One bite of these caramelized, pineapple-packed delights, and you’ll feel like you’ve brought the taste of the tropics straight to your kitchen—one sweet, golden cupcake at a time!