Pineapple Upside Down Cupcakes

These retro-inspired cupcakes make things in the kitchen a little more convenient by using a yellow cake mix. Pineapple Upside Down Cupcakes are moist, full of caramel and pineapple flavor, and eye-catching with their pineapple and cherry design!

Pineapple Upside Down Cupcakes are a classic dessert inspired by pineapple upside-down cake. This easy recipe transforms a boxed cake mix into a moist and sweet cake that melts in your mouth. They bake upside down, just like the cake version. The brown sugar and butter mixture caramelizes over the pineapple slices and cherries, creating a sinfully sweet topping. The cake mixture is incredibly moist and pineapple flavored, thanks to the addition of the juice leftover from the can.

I’ve always loved the classic pineapple upside down cake and wanted to make a cupcake version. Think mini pineapple upside down cakes that are super cute and so simple to make. I’ve made Pineapple Upside Down Cake many times in the past, but I’ve never made it in a cupcake form until now.

Why You’ll Love This Recipe

• All the deliciousness of pineapple upside down cake, but in a convenient cupcake form.
• Easy cake recipe made with a box mix in a cupcake pan.
• ​Ready to enjoy in less than an hour.
• Makes 18 cupcakes.
• A retro dessert to remind you of times past.
• Great taste with loads of sweet pineapple and cherries.
• Simple ingredients are readily available at the grocery store.

Ingredients

The full printable recipe card with measurements and instructions is found at the bottom of the post.

• Pineapple slices: Reserve the pineapple juice from the can.
• Yellow cake mix
• ​Large eggs
• Vegetable oil
• Salted butter
• Brown sugar
• Maraschino cherries

How to Make Pineapple Upside Down Cupcakes

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Follow along to learn how to make pineapple upside down cupcakes.

• Step One: Preheat oven to 350°F. Spray muffin tins with cooking spray. Set aside.
• Step Two: Add cake mix, vegetable oil, pineapple juice (this is the juice you saved from the can of pineapple), eggs to a large bowl and beat with an electric mixer on medium speed until smooth.

• Step Three: Mix brown sugar and butter in a small bowl. Add a small spoonful of brown sugar mixture to each muffin tin. 

• Step Four: Then add two pineapple slices to each muffin tin. Place a cherry half, cut side up, in the centre of the pineapple slices. Using a cookie scoop or spoon, add cake batter to each muffin tin.

• Step Five: Bake for 20 minutes, or until a toothpick inserted into the center of the cupcakes comes out clean. Let cool for a few minutes, then invert onto a baking rack.

What to Serve with Them

• Whipped cream: Add a dollop of whipped cream (try my homemade Cool Whip) to your cupcake.
• Vanilla ice cream: Serve your warm cupcake with a scoop of homemade vanilla ice cream.
• Caramel sauce: Drizzle homemade caramel sauce on the cupcake for extra decadence.
• Fresh berries: Add some fresh berries for a burst of sweetness.
• ​Sweetened coconut flakes: Sprinkle toasted coconut on top for a tropical twist.

Variations and Substitutions

• ​Experiment with other fruits. Switch out the pineapple for peaches, cherries, apples, pears, or a combination of fruits. 
• Add a boost of flavor. Try spices like cinnamon or nutmeg in the cake batter or extracts like vanilla, almond, or coconut. Pineapple extract would be good, too!
• Include nuts for extra crunch. If you like nuts, add chopped pecans, walnuts, or almonds to the cake batter or the fruit topping.
• ​Try another cake mix flavor. You can try white cake mix if you don’t have yellow cake mix. 
• Use pineapple tidbits instead of pineapple rings. You can also use fresh pineapple, but be sure to add pineapple juice, as you aren’t using canned pineapple. Place the cherry in the center of the pineapple pieces.

Storage Instructions

Let the cupcakes come to room temperature before you store them. You can wrap them individually in plastic wrap or store them in an airtight container. Store in the refrigerator for 3-4 days. 

Can You Freeze?

Yes, you can freeze them! Wrap the cupcakes in plastic wrap or place them in an airtight container. I also recommend wrapping them again in aluminum foil or putting them in a freezer bag to prevent freezer burn. They’ll keep them in the freezer for 2 to 3 months when stored properly.

To thaw, place the cupcakes in the refrigerator overnight. Once they are thawed, you can place them on the counter to bring them to room temperature or warm them slightly in the oven or microwave.

Recipe Tips and Tricks

• Remember to grease the cupcake pan to prevent the cupcakes from sticking to it. Nothing is worse than making cupcakes and being unable to remove them from the pan.
• ​Avoid overmixing. Do not overmix the cupcake batter, or you will end up with tough, dense cupcakes. Mix the ingredients until just combined and smooth.
• After removing the cupcakes from the oven, let them cool for a few minutes. Then, carefully flip them onto a wire baking rack.
• Cut your pineapple rings to make them fit into the cupcake tin.
• Test for doneness with a toothpick. When inserted into the middle of a cupcake, it should come out clean.

What If I Don’t Have Pineapple Rings? 

Are you all out of pineapple rings? You can use pineapple chunks if you prefer. You might want to slice them down so they are not so thick. I find that helpful, and then just add enough to cover the bottom of each cupcake spot. 

I know it is traditional for rings, but feel free to improvise. We love making them, and I have used other forms of pineapple as well. Crushed pineapple is my least favorite, as it blends in with the cake and doesn’t leave a distinct layer. 

How to Flip

1. Make sure the cupcakes have cooled down after removing them from the oven. I usually let mine cool for between 5 and 10 minutes. They’ll be easier to flip.
2. Place a cooling rack or a baking sheet on top of the cupcake pan, making sure it covers the entire pan.
3. Put on some oven mitts and hold the pan and cooling rack with both hands. Ensure you have a firm grip to avoid mishaps (Been there, done that!).
4. Once you’ve flipped, gently tap the bottom of the cupcake with the back of a spoon or your fingers to loosen any that might be stuck. You can also gently shake the pan if necessary.
5. ​Slowly lift off the cupcake pan. Make sure to lift straight up and away from the cupcakes.
6. Take a look at the cupcakes to adjust any shifted toppings. Gently press any loose toppings back onto the cupcakes.
7. Allow to cool and serve!

FAQ

Cupcake Recipes

• Coconut Cream Pie Cupcakes
• Death By Chocolate Cupcakes
• Cherry Coke Cupcakes
• Banana Cupcakes

You might also like Pineapple Tarts, Pineapple Sticky Buns, Pineapple Dip, Pineapple Cake and Pineapple Pie.

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