Pineapple Upside Down Cupcakes

A fun twist on the classic cake recipe, these pineapple upside down cupcakes have the perfect hint of pineapple flavor!

These tropical pineapple upside down cupcakes are a great addition to any BBQ or get-together. If you love the classic Pineapple Upside Down Cake, then these individualized treats are sure to be a hit anywhere you take them.

classic Cake in Cupcake Form

Whenever I eat pineapple upside-down cake, it always brings back fond memories of family gatherings. It’s a popular recipe during holidays like Christmas and Easter, but we also love enjoying it during the summer. There’s nothing more refreshing than pineapple flavor

For a fun twist on the classic cake recipe, I decided to try a cupcake version! I couldn’t be more pleased with how they turned out. All the amazing tastes of pineapple-flavored cake, with caramelized pineapple slices and cherries on top, but in individual serving sizes.

Pineapple upside-down cupcakes are just as simple—if not simpler—to make, and are a crowd-pleaser. Everyone loves them, especially the kids. Plus, are they not adorable?!

How to Make Pineapple Upside Down Cupcakes

Pineapple upside down cupcakes with cake mix are so simple to make and are delightful tropical.

PREP. Preheat the oven to 350°F. Prepare 24 wells of a muffin tin by spraying with cooking spray.

CAKE. In a large bowl, mix together the pineapple juice, yellow cake mix, oil, and eggs until well blended.

FRUIT. Cut each of the pineapple rings into four equal-sized pieces. Mix together the butter and brown sugar, and add about 1 teaspoon of the butter mixture to each well of the muffin tin. Add two pieces of pineapple and a maraschino cherry half, cut side up.

BAKE. Pour the cake batter into the cupcake tin, filling to about ¼ inch from the top. Bake 20-25 minutes, or until golden brown. Remove from oven and let cool 15 minutes, then loosen the cupcakes from the sides of the muffin tin with a knife and invert onto a cooling rack.

Serve warm with freshly Whipped Cream, if desired.

Recipe Tips

This pineapple upside down cupcake recipe is pretty magical. The pineapple adds the perfect amount of brightness.

Pineapple. You can cut the rings into smaller sections or buy a 20-ounce can of pineapple chunks or even use crushed pineapple or pineapple tidbits.  

The amount of pineapple juice should equal to 1 cup. If you are shy, add water to the juice to get 1 cup.

Liners. I don’t recommend lining the muffin cups with paper cupcake liners, however, you can use reusable silicone liners. 

Cake mix. The yellow cake mix can be substituted with a pineapple cake mix.

Flipping Tips

Flipping the cupcakes is the hardest part, and even then, it’s not too difficult. Here are some tips to help you flip the cupcakes.

• Wait a few minutes for the little cakes to cool a bit.
• Use a sharp paring knife or a small rubber spatula and slide it around each cake releasing the sides from the pan.
• Flip the cupcake pan onto wax paper.
• Allow the cupcakes to sit for another few minutes with the pan still covering them.
• The cakes should begin to plop down on their own. Carefully remove the pan.

Voila – not too hard, right?!

Storing Info

STORE. Store the pineapple upside down cake cupcakes in the fridge, in an airtight container, for about 3 days.

FREEZE. To store in the freezer, allow the cupcakes to cool and flash freeze by placing them in the freezer for about an hour. Take the cupcakes out, wrap them with plastic wrap, then again with foil.

Or place the wrapped cupcakes in a freezer-safe container. Label and freeze for 2-3 months. 

Recipe FAQ

For More Fruity Cupcake Recipes, Try:

• Banana Cupcakes
• Strawberry Lemonade Cupcakes
• Cherry Almond Cupcakes
• Fresh Strawberry Cupcakes
• Cherry Cheesecake Cupcakes

adapted from Betty Crocker