Pineapple Upside Down Cupcakes

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These pineapple upside down cupcakes take all the flavors of a traditional upside down cake and makes it in the perfect portion size. A maraschino cherry in the center of a brown sugar pineapple filling, covered with moist pineapple cake batter, and baked “upside down”.

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

I love pineapple upside-down cake but I also love cupcakes. The combination of the two in these cupcakes make for one of the best desserts ever. I love making these pineapple upside down cupcakes for all occasions. They are a huge hit for parties and get-togethers and are perfect for bake sales.

We love making upside down desserts like our strawberry upside down cake, banana upside down cake, southern upside down pecan cake, peach upside down cupcakes and apple upside down cake.

Ingredients You Will Need

  • Pineapple Cake Mix any brand is fine to use or you can also use yellow cake mix if you can’t find pineapple. You’ll combine the cake mix with eggs and oil.
  • Pineapple juice – I always have small cans of pineapple juice, but you can use the drained juice from the can of crushed pineapple.
  • Butter – unsalted or salted is fine to use, whatever you have on hand. You will need to melt the butter which can be done in the microwave. Start by heating for 30 seconds and then an additional 10 seconds until the stick of butter is completely melted.
  • Brown sugar – this is sprinkled over the melted butter in the muffin pan and creates this amazing glaze over the baked cupcakes.
  • Pineapple – we used a can of crushed pineapple, but sliced pineapple can also be used. We show you the difference in the images below.
  • Maraschino cherries – this is optional, but adds a nice touch to these pineapple cupcakes for not only flavor, but also the finished look.
ingredients for Upside Down Pineapple Cupcakes

How to Make Pineapple Upside Down Cupcakes

Start with a preheated oven to 350 degrees. Spray the cupcake pans with nonstick baking spray.

  • In a bowl, using a mixer,  mix together the cake mix, oil, eggs and pineapple juice on low speed until well mixed. Once mixed, then beat the batter for 2 minutes on medium speed.
  • Spoon 1 tablespoon of butter into the bottom of each cup.
  • Next, add 2 teaspoons of brown sugar to each cup and top with a cherry in the center.
  • Add 1 tablespoon of pineapple to each cup and press it down.
  • Fill the cups with the cake batter almost the top of the cups.
  • Bake the cupcakes on the center rack for 20 minutes or until they are done. Insert a toothpick in the center comes out clean. DO not push all the way to the pineapple mixture.
  • Allow the cupcakes to cool on a cooling rack and then turn the pan over into another pan or covered surface.
tops of Pineapple Upside-Down Cupcakes

Can I Use Fresh Pineapple for These Cupcakes?

These pineapple cupcakes are just the right amount of pineapple to cupcakes when you use the crushed pineapple. However, you can use fresh pineapple if you choose. You will want to make sure that the pineapple is chopped into as small of pieces as possible. I would recommend running it through a food processor.

Do Upside-Down Cupcakes Have to Be Refrigerated?

While most cakes do not need to be refrigerated, since this cake has fruit in it, you will want to store it in the refrigerator. Always keep cakes that have fresh fruit or a perishable frosting like a cream cheese frosting in the refrigerated.

sides of Pineapple Upside Down Cupcakes

Variations & Tips

  • Sub the pineapple cake mix for yellow cake mix – you won’t have as much of a pineapple flavor, but this will work just fine.
  • Why are my pineapple cupcakes soggy? This could be because of the amount of liquid added in from the fruit. Making sure your pineapple and cherries are drained well will eliminate this issue.
  • Toppings: take this pineapple dessert up a notch with adding homemade whipped cream or vanilla ice cream.
  • Replace the crushed pineapple with sliced pineapple – simple cut the sliced pineapple in half, then in half again and place the cute slices into the muffin cups on top of the brown sugar like this…
Collage or Upside-Down Pineapple Cupcakes

Other Pineapple Desserts You Will Love:

Upside Down Pineapple Cupcakes feature
5 from 15 votes

Pineapple Upside Down Cupcakes

These pineapple upside-down cupcakes take all the flavors of a traditional upside down cake and makes it in the perfect portion size. These light and fluffy cupcakes make the perfect cupcake for an easy weeknight dessert or for a special occasion.
Servings: 24
Prep: 15 minutes
Cook: 20 minutes
Total: 35 minutes



  • Preheat oven to 350 degrees.
  • Spray two 12 count cupcake pans with non-stick cooking spray.
  • Mix cake mix, oil, eggs and pineapple juice on low speed of mixer until combined. Switch to med. Speed and mix for about 2 min.
  • Spoon 1 teaspoon melted butter in bottom of each cupcake cup.
  • Add 2 teaspoons brown sugar to each cup.
  • Place a cherry in the center of the cups.
  • Add 1 Tablespoon of the crushed pineapple to each cup and pack down.
  • Fill the cups with the cake batter to just below the tops of each cup.
  • Bake on center rack of oven for 20 min. or until toothpick inserted in center comes out clean.
  • Only push toothpick part way into the cupcake so you don’t reach it into the pineapple mixture.
  • Allow to cool in pan on baking rack for 5 min., then invert onto another pan or wax paper covered surface. Turn each cupcake right side up.

Last Step:

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Serving: 24g | Calories: 205kcal | Carbohydrates: 23g | Protein: 1g | Fat: 13g | Saturated Fat: 6g | Polyunsaturated Fat: 3g | Monounsaturated Fat: 3g | Trans Fat: 0.3g | Cholesterol: 41mg | Sodium: 73mg | Potassium: 91mg | Fiber: 1g | Sugar: 22g | Vitamin A: 289IU | Vitamin C: 5mg | Calcium: 27mg | Iron: 0.4mg


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16 comments on “Pineapple Upside Down Cupcakes”

  1. 5 stars
    I just made a batch and one pan looks normal but the other pan has the pointy tops like someone else mentioned. Does anyone know why this happens? I have no doubt they’ll still get devoured though lol Thanks for the recipe!

  2. I did my turn up with a pointed top. They look like hats delicious but had a weird pointy top. Maybe when I flip them the flat now hopefully

  3. 5 stars
    Came out beautifully! If you are counting calories, this is the way to go. Takes a little more time than a cake.

  4. 5 stars
    Can I make these in the 6 section muffin tins, since they are quite a bit larger than the 2 section cup cake tin.

    1. Hi Kathryn. I have not tried that, but the recipe yield for the 24 small should still work for the 12 large. Let me know how they turn out!

  5. 5 stars
    I used this recipe to make individual pineapple upside down cakes. I put 1 t. Melted butter, 2 t. brown sugar, 1/2 maraschino cherry, and surrounded the cherry with pineapple tidbits. Topped all with the cupcake batter and baked. It made 4. Topped with whipped cream. So easy and delicious!