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
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.
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.
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.
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…
Other Pineapple Desserts You Will Love:
- Pineapple Whoopie Pies
- Pineapple Whip Pie
- No-Bake Pineapple Dream Dessert
- Pineapple Poke Cake
- Hummingbird Cake
Pineapple Upside Down Cupcakes
Ingredients
- 1 box Pineapple Cake Mix can use yellow
- 3 eggs
- 1/2 cup vegetable oil
- 1 cup pineapple juice
- 1 cup melted butter
- 1 1/2 cups brown sugar
- 4 cups crushed pineapple drained
- 24 maraschino cherries patted dry
Instructions
- 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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30 comments on “Pineapple Upside Down Cupcakes”
Use Pam in tins and they come out perfect.
Cupcakes stuck, put parchment paper circle down first before layering sugar, pineapple and cherry & batter. They will pop out clean and then you can remove parchment paper. Other than that, they are delicious
Are you sure you meant a CUP of butter? I thought that was overkill and thought maybe you meant 1 stick(1/2cup) and it was perfect amount
Hi Cindy. Yes, it is 1/2 cup. That is a typo that I will update. Thanks!
Help! In the description above you said spoon 1 TABLESPOON of melted butter in the bottom, but in the actual recipe you wrote spoon 1 TEASPOON of melted butter. Which is it? I’m about to put them in the tins and place them in the oven and I’m bringing them to a party but this is a big discrepancy. Can you please clarify? Thank you!
Hi Shannon. Sorry about that. I will correct it. You will use one teaspoon melted butter in the bottom.
Thanks so much! That was what I ended up doing because I figured one tablespoon would be way too much. I did end up though with an extra half cup of melted butter. So I’m wondering if the total quantity needed correction on the recipe, too? Anyway they are delicious! Everyone will love them today. Thank you so much!
Thank you Shannon!
Can I freeze them to have when unexpected guests arrive?
Hi Cindy. Yes, these cupcakes will freeze well. You will want to remember to thaw them for several hours prior to serving.
It was so delicious that when I shared some with neighbors, they all want to pay for more supplies so I can make them each a batch. Soooooo good!!!
That’s awesome Fani! Thanks!
Very clear and precise instructions.
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!
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
Cut the tops off before you flip them out of the pan
that are great, everyone loves them, I make them all the time.
Thank you Michele!
Came out beautifully! If you are counting calories, this is the way to go. Takes a little more time than a cake.
Thanks Jamee!
I loved them and want to upliad a picture but can’t see a way to do that
Can I make these in the 6 section muffin tins, since they are quite a bit larger than the 2 section cup cake tin.
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!
Could I freeze them for later
Yes, these will freeze ok.
These cupcakes are AMAZING! It’s really hard to not eat them all! Thanks for the great recipe!
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!
Made these for church meeting. Everyone loved them, easy and pretty to serve and make,!
Looks yummy
THANKS I HAVE BEEN LOOKING FOR THIS RECIPE FOR AT LEAST YRS. I BOUGHT A SPECIAL PAN FOR IT THE LOST RECIPE