Pineapple Upside Down Cupcakes
Pineapple Upside Down Cupcakes – a mini version of your favorite cake in cupcake form with butter, brown sugar, pineapple, and a cherry on top! These cupcakes are good warm or at room temperature so they’re a great recipe for parties or luaus.

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Pineapple Upside Down Cupcakes
In a perfect world, I would make these from scratch. And by all means if you want to, go right ahead.
But sometimes a doctored up cake mix does wonders. I mean adding brown sugar and butter to cake mix? Sounds like a sure win to me.
This Pineapple Upside Down Cupcakes recipe has been calling to me for years. Try not to burn the top of your mouth off eating them straight out of the oven. I did.

WHAT ARE PINEAPPLE UPSIDE DOWN CUPCAKES?
Pineapple Upside Down Cupcakes are a mini version of your favorite cake with butter, brown sugar, pineapple, and a cherry on top!
- First, spoon a little bit of melted butter, pineapple, brown sugar, and a cherry in the bottom of a muffin tin.
- Next, top with the cupcake batter and bake.
- Finally, invert the cupcakes for beautiful Pineapple Upside Down Cupcakes.
I always have plenty of helpers in the kitchen. My son poured a teaspoon (or two) of butter in each cupcake tin. Then he put a tablespoon of brown sugar on top.
Then he put a cherry right in the center of the brown sugar.
I tried using crushed pineapple, pineapple slices, and pineapple tidbits to see which one worked better. I liked the crushed pineapple and tidbits the best.
The tidbits give a nice flower shape but the pineapple flavor is not as strong as using crushed pineapple so your choice.
The cupcake batter is just made according to the package directions but with replacing the water in the recipe with pineapple juice. Make sure you don’t over fill your tins.
Invert cupcakes onto waxed or parchment paper and you’re done!

WHAT’S THE BEST CUPCAKE PAN?
The Wilton Perfect Results Cupcake Pan is great for baking Pineapple Upside Down Cupcakes and is only $15 at Amazon. It only features 12 cups, so you’ll need two to make all 24 cupcakes at once. You can also bake half at once, which will take a little more time. I also like to use cupcake liners to make sure they don’t stick to the pan!
OTHER FRUIT RECIPES
- Easy Fruit Dip
- Poppy Seed Fruit Salad
- Grape Walnut Salad
- Peach Cobbler Recipe
- Fruit, Avocado, and Feta Salad
- Fruit Pizza
- Snickers Apple Salad
- Apple Crisp Pizza
OTHER CUPCAKE RECIPES:
- Rainbow Cupcakes
- Reese’s Peanut Butter Cupcakes
- Strawberry Puffcakes
- Strawberry Colada Cupcakes
- Strawberry Milkshake Cupcakes
- Funfetti Cupcakes

Pineapple Upside Down Cupcakes
Ingredients
- 1/2 cup butter, melted
- 1 1/2 cups brown sugar
- 24 maraschino cherries
- 1 (20 ounce) can crushed pineapple or pineapple tidbits (well drained but reserve juice)
- 1 (15.25 ounce) package yellow cake mix, (and ingredients called for on the package)
- 1 cup pineapple juice, (you just need as much pineapple juice as water called for on the cake mix package - see note)
- powdered sugar for dusting
Equipment
Instructions
- Preheat oven to 350 degrees and line 24 muffin cups with baking cups.
- Line a work surface with parchment or waxed paper.
- Spoon 1 teaspoon melted butter into the bottom of the pan of each sprayed muffin cup.
- Spoon 1 tablespoon brown sugar in each muffin cup.
- Press a maraschino cherry into the center of the brown sugar in each muffin cup.
- Spoon a tablespoon of well drained crushed pineapple or about 5 pineapple tidbits over the cherry into an even layer.
- Mix cake mix according to the package directions, substitute pineapple juice for the water in the recipe. This may vary according to which cake mixture you use. In large bowl with electric mixer on low speed until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.
- Scoop pineapple cake batter into the muffin cups, filling them 3/4 of the way full.
- Bake in the preheated oven on the middle rack until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
- Allow cupcakes to cool for about 20 minutes. Unwrap cupcakes and invert onto a serving platter. Serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with powdered sugar if desired.
Notes
*Some people like the look of pineapple tidbits better for this recipe. I tried both and it's really just personal preference.


