These Pineapple Upside Down Cupcakes (with cake mix) are so moist and full of pineapple flavor! They start with a doctored up pineapple box cake so they're a breeze to make!
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How to make pineapple upside down cupcakes:
The first step is making the topping, aka: the best part! It's a combination of brown sugar, butter, and pineapple...basically heaven!
This recipe makes 24 pineapple upside down cupcakes. If you want to make them all in one batch, here's a great option for a 24 cup muffin pan. and even though these start with butter in each muffin cup, I still highly recommend spraying the pan with non-stick spray. The butter mixes with the brown sugar and is very sticky so the non-stick spray is very helpful!
Once you add in the butter, you can sprinkle in the brown sugar. I like to use my clean fingers to just move it around so that it lays evenly in the melted butter and kind of sinks down into it.
After, adding the brown sugar, you can add the maraschino cherries. These are totally optional but I think they make the pineapple upside down cupcakes look so cute and look like a traditional pineapple upside down cake.
Next comes the crushed pineapple. You'll want to drain it with a mesh strainer before adding it to the muffin tins. Make sure you drain it over a bowl or measuring cup and save all the pineapple juice because we'll be using that for the cake mix!
Once you've assembled the topping, you can move on to the cake batter. I like to use the Duncan Hines pineapple supreme cake box but you could also use a regular yellow cake if you can't find that.
You'll make the cake just as it's directed on the box except for 2 changes. You'll substitute the water for pineapple juice and add an additional teaspoon of vanilla extract. If you are a little short on pineapple juice, you can just use water for the remaining liquid.
You'll also add the oil and eggs that are called for on the cake box. Once you've mixed the cake batter, you can add it into the muffin tin cups. You'll want to fill them about ¼ inch from the top.
Now you're ready to bake! These take about 18-20 minutes.
How to tell when pineapple upside down cake is done baking:
Just like most cakes, you can use a toothpick to insert in the center of the cupcake. Try to stay in the middle and not go all the way down into the brown sugar. If the toothpick comes out mostly clean and not wet, they're done!
After about 5-10 minutes, you can flip these over onto a sheet of parchment or wax paper. The cakes are slightly sticky so this helps them not rip apart on the bottom.
Other Recipes You'll Love:
- Blueberry Muffins with Cinnamon Topping
- Baked Hawaiian Chicken Kabobs
- Old Fashioned Apple Crisp
- THE BEST Broiled Salmon
Pineapple Upside Down Cupcakes (with cake mix)
Equipment
- cup muffin tin
- parchment or wax paper
- Non-stick spray
Ingredients
- ½ cup butter melted
- 1 and ½ cup brown sugar
- 24 maraschino cherries (stem removed)
- 20 ounce can of crushed pineapple (drain and save the juice)
- 1 box Pineapple Supreme Cake Mix
- 1 cup reserved pineapple juice
- ½ cup canola oil (or what cake mix calls for)
- 3 eggs
- 1 teaspoon vanilla extract
Instructions
- Pre-heat your oven to 350° and spray your muffin tin very well with non-stick spray.
- Pour 1 teaspoon of melted butter into each muffin cup.
- Add 1 tablespoon of brown sugar to each muffin cup and press gently into the butter.
- Press 1 cherry in the center of each muffin cup
- Drain the crushed pineapple and save the juice and set it aside.
- Add 1 tablespoon of the crushed pineapple and add it to each muffin cup and spread evenly around the cherry.
Preparing the cake mix
- In a large bowl, prepare the cake mix as directed on the box but substitute the water for the reserved pineapple juice. (if you are short on pineapple juice, you can top it off with water)
- Add in the oil and eggs as shown on the cake mix box and add an additional 1 teaspoon of vanilla extract. Mix well until you see no more dry spot in the batter.
- Add the cake batter to each muffin cup until each up is almost full (see photos above)
- Bake for 18-20 minutes or until a toothpick inserted in the center of a cupcake comes out clean.
- Allow the cupcakes to cool for about 10 minutes, then flip them onto either parchment or wax paper to prevent them from sticking. Serve warm for the best flavor!
Abigail says
Hi Mindy, I'm a housewife, today I followed your recipe and made this delicious food, to be honest I'm not very good at it, but the good thing is that your recipe is very detailed step by step, I managed to make it, thank you!