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 are so eye catching with the pineapple and cherry design!

Pineapple Upside Down Cupcakes are a classic dessert inspired by pineapple upside-down cake. In this easy recipe, a boxed cake mix gets transformed 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 cherry creating a sinfully sweet topping. The cake mixture is incredibly moist and pineapple flavoured thanks to the addition of the juice leftover from the can.

I’ve always 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.

I’m a big fan of cake mix hack recipes. Magic happens in a cupcake tin and I’m loving the sweet result!

Why You’ll Love Pineapple Upside-Down Cupcakes

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

Ingredients

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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

• 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: In a small bowl, stir together brown sugar and butter. Add a small spoonful of brown sugar mixture to each muffin tin. 

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

• Step Five: Bake for 20 minutes or until a toothpick comes out clean from the center of the cupcakes. Let cool for a few minutes and then invert on a baking rack.

Equipment Needed

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• ​Cookie scoop
• Cupcake pan
• Mixer
• Mixing bowls

What to Serve with Pineapple Upside Down Cupcakes

• 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 top of 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 some spices like cinnamon or nutmeg to 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. If you don’t have yellow cake mix, you can try white cake mix. 
• Use pineapple tidbits instead of pineapple rings. You can also use fresh pineapple, but you will need to add pineapple juice since you aren’t using canned pineapple. Place the cherry in the center of pineapple pieces.

Storage Instructions

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

Can You Freeze Pineapple Upside Down Cupcakes?

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

To thaw, place the cupcakes in the refrigerator overnight. Then 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

• Don’t forget to grease the cupcake pan to prevent them from sticking. There’s nothing worse than making cupcakes and not being able to remove them from the pan.
• ​Avoid overmixing. It’s important to not overmix the cupcake batter or you’ll end up with tough, dense cupcakes. Mix the ingredients until just combined and smooth.
• Let the cupcakes cool for a few minutes after removing from the oven. Then you can careful flip them onto a wire baking rack.
• Cut your pineapple rings if you need to make them fit into the cupcake tin.
• Test for doneness with a toothpick. It should come out clean when inserted into the middle of a cupcake.

What If I Don’t Have Pineapple Rings? 

All out of pineapple rings? Well you can use pineapple chunks if you would like. You might want to slice them down so they are not so thick. I find that is 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 in the past. Crushed pineapple is my least favorite as it kind of blends in with the cake, and doesn’t leave that defined layer. 

How to Flip Pineapple Upside Down Cupcakes

1. Firstly, make sure the cupcakes have cooled down after removing from the oven. I usually let mine cool between 5 to 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 together with both hands. Make sure you have a firm grip to avoid any 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 cupcakes that might be stuck. you can give the pan a gentle shake if you need to.
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 toppings that might have shifted. You can gently press any loose toppings back onto the cupcakes.
7. Allow to cool and serve!

FAQ

Cupcake Recipes

• Coconut Cream Pie Cupcakes: Here is a fantastic coconut recipe that is going to give you that coconut cream pie flavor in every single indulgent bite. A must-make for any coconut fan. 
• Death By Chocolate Cupcakes: Chocolate lovers unite over this sinfully tasty cupcake. A chocolate cupcake topped with a rich and smooth chocolate frosting. 
• Cherry Coke Cupcakes: If you love the cherry and coke combo, here is a cherry coke cupcake that we enjoy. Moist cake, rich frosting and a maraschino cherry on top. 
• Banana Cupcakes: Grab those overripe bananas and skip banana bread and make a cupcake instead. Moist and loaded with banana flavor. 

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

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