Pineapple Upside Down Cupcakes (Easy Mini Cakes)

These fun and personal-sized Pineapple Upside Down Cupcakes are a mini version of your favorite cake in cupcake form! Buttery pineapple cake mix, sweet brown sugar drizzle, pineapple pieces, and finished with a cherry on top.

For a classic Pineapple Upside Down Cake – that is homemade with no cake mix – try this recipes that bakes up in a round cake pan. 

Pineapple Upside-Down Cupcakes (Easy With A Cake Mix)

Pineapple upside down cupcakes are the mini version of your favorite cake in cupcake form 🍍🍒. The classic dessert is turned into a mini cake, or the cupcake version, inside a muffin pan. 

Loaded with sweet and juicy pineapple flavor from the crushed pineapple pieces, and the buttery and fluffy vanilla cupcake base with pineapple juice in it! Simple to make with a boxed cake mix – only a total of 7 ingredient needed. 

How To Make Easy Pineapple Upside-Down Cake In Cupcakes (Printable Recipe Card)

Preheat the oven to 350 degrees F. Prepare two 12-cup standard muffin tins by spraying each of the muffin cups with nonstick cooking spray. Set aside. 

Drain the canned crushed pineapple making sure to place a bowl below the strainer to catch the liquid. Reserve 1 cup of the strained pineapple juice for the cake batter. Set the pineapple juice aside and the crushed pineapple. 

In a large bowl, add the yellow cake mix, 1 cup reserved pineapple juice, large eggs, and vegetable oil. Using an electric mixer or stand mixer, beat the ingredients on low speed until combined, then increase the speed to medium for 2 minutes. 

In a small bowl, combine the melted butter and light brown sugar. 

Add 1 whole maraschino cherry to the center of each muffin cup. Then spoon 1 teaspoon of the brown sugar butter mixture over top the cherry, ensuring it covers the bottom of the muffin cup. Next, spoon 1 tablespoon of the drained crushed pineapple (set aside from earlier) over the brown sugar mixture avoiding the top of the cherry. 

Gently spoon or pipe the yellow cake batter over each muffin cup filling to about 1/4-inch from the top of the muffin cup. 

Place the cupcakes in the oven and bake for 20-25 minutes or until a toothpick inserted into the cake part comes out clean. 

Cool for 5 minutes on a wire cooling rack, then gently remove the cupcakes by inverting the pan using the cooling rack as a backstop. Garnish each one with fresh whipped cream (homemade, Cool Whip, or store-bought spray cream). 

Serve the pineapple upside down cakes warm. Enjoy!

How To Store Leftovers

I recommend serving these fresh, but the leftover are yummy as well as the flavors have had time to intensify, place the leftovers inside an airtight container and store in the refrigerator for up to 2-3 days. 

Tips For Success

• Use plenty of cooking spray in each cupcake tin to ensure the cupcakes come out smoothly. 
• Leave enough space in each muffin cup for the cake batter to expand. Be careful not to overfill or else the cake batter will spill over. Leave about 1/4-inch of space between the top of the cake batter and the top of the muffin cup. 
• When draining the crushed pineapple make sure you place a bowl underneath the strainer to catch the pineapple juice! You will need it for the yellow cake mix mixture to give it that fresh pineapple flavor. 
• I prefer the smaller texture of the crushed pineapple in these mini cakes, but you can also use pineapple tidbits or pineapple rings instead. The rings are bigger and thicker, which means more pineapple and less room for the cake mixture. 
• Use a yellow cake mix, buttery golden cake mix, or even a white cake mix. I think the flavor of the yellow cake or buttery golden cake mix tastes the best. 
• I prefer serving these warm (after they have had the cool down time after cooking), but you can also serve them closer to room temperature if wanted. But, I think warm is best because then the brown sugar drizzle is melty and warmed, and just soaks into the mini cakes. 

My serving suggestion for pineapple upside down cupcakes is to add a dollop of whipped cream on top – make homemade whipped cream, use spray whipped cream, or even Cool Whip

More Pineapple Desserts

• Pineapple Dream Dessert
• Pineapple Pretzel Salad
• Pineapple Pistachio Cake
• Pineapple Cherry Dump Cake
• Mango Pineapple Popsicles