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A fun twist on the classic cake recipe, these pineapple upside down cupcakes have the perfect hint of pineapple flavor!
These tropical pineapple upside down cupcakes are a great addition to any BBQ or get-together. If you love the classic Pineapple Upside Down Cake, then these individualized treats are sure to be a hit anywhere you take them.
classic Cake in Cupcake Form
Whenever I eat pineapple upside-down cake, it always brings back fond memories of family gatherings. It’s a popular recipe during holidays like Christmas and Easter, but we also love enjoying it during the summer. There’s nothing more refreshing than pineapple flavor
For a fun twist on the classic cake recipe, I decided to try a cupcake version! I couldn’t be more pleased with how they turned out. All the amazing tastes of pineapple-flavored cake, with caramelized pineapple slices and cherries on top, but in individual serving sizes.
Pineapple upside-down cupcakes are just as simple—if not simpler—to make, and are a crowd-pleaser. Everyone loves them, especially the kids. Plus, are they not adorable?!
How to Make Pineapple Upside Down Cupcakes
Pineapple upside down cupcakes with cake mix are so simple to make and are delightful tropical.
PREP. Preheat the oven to 350°F. Prepare 24 wells of a muffin tin by spraying with cooking spray.
CAKE. In a large bowl, mix together the pineapple juice, yellow cake mix, oil, and eggs until well blended.
FRUIT. Cut each of the pineapple rings into four equal-sized pieces. Mix together the butter and brown sugar, and add about 1 teaspoon of the butter mixture to each well of the muffin tin. Add two pieces of pineapple and a maraschino cherry half, cut side up.
BAKE. Pour the cake batter into the cupcake tin, filling to about ¼ inch from the top. Bake 20-25 minutes, or until golden brown. Remove from oven and let cool 15 minutes, then loosen the cupcakes from the sides of the muffin tin with a knife and invert onto a cooling rack.
Serve warm with freshly Whipped Cream, if desired.
Recipe Tips
This pineapple upside down cupcake recipe is pretty magical. The pineapple adds the perfect amount of brightness.
Pineapple. You can cut the rings into smaller sections or buy a 20-ounce can of pineapple chunks or even use crushed pineapple or pineapple tidbits.
The amount of pineapple juice should equal to 1 cup. If you are shy, add water to the juice to get 1 cup.
Liners. I don’t recommend lining the muffin cups with paper cupcake liners, however, you can use reusable silicone liners.
Cake mix. The yellow cake mix can be substituted with a pineapple cake mix.
Flipping Tips
Flipping the cupcakes is the hardest part, and even then, it’s not too difficult. Here are some tips to help you flip the cupcakes.
- Wait a few minutes for the little cakes to cool a bit.
- Use a sharp paring knife or a small rubber spatula and slide it around each cake releasing the sides from the pan.
- Flip the cupcake pan onto wax paper.
- Allow the cupcakes to sit for another few minutes with the pan still covering them.
- The cakes should begin to plop down on their own. Carefully remove the pan.
Voila – not too hard, right?!
Storing Info
STORE. Store the pineapple upside down cake cupcakes in the fridge, in an airtight container, for about 3 days.
FREEZE. To store in the freezer, allow the cupcakes to cool and flash freeze by placing them in the freezer for about an hour. Take the cupcakes out, wrap them with plastic wrap, then again with foil.
Or place the wrapped cupcakes in a freezer-safe container. Label and freeze for 2-3 months.Â
Recipe FAQ
Be sure to remove them before they have a chance to cool off too much. If you wait too long the sugary topping will cool into a sticky syrup which will make it harder to remove the cupcakes successfully. If you wish, you can cut small rounds out of parchment paper to add to the bottom of each cupcake well.
The tops will be sticky but the base should not be soggy. Be sure to use the ingredients listed on the recipe card and do not follow the box directions, drain the pineapple and cherries, and bake until a toothpick inserted into the center comes out clean or with a few moist crumbs.
For More Fruity Cupcake Recipes, Try:
- Banana Cupcakes
- Strawberry Lemonade Cupcakes
- Cherry Almond Cupcakes
- Fresh Strawberry Cupcakes
- Cherry Cheesecake Cupcakes
Pineapple Upside Down Cupcakes Recipe
Ingredients
- 1 (20-ounce) can pineapple rings drained and juice reserved
- 1 (15.25-ounce) box yellow cake mix
- ½ cup vegetable oil
- 3 eggs
- â…“ cup butter melted
- â…” cup brown sugar packed
- 12 maraschino cherries cut in half
Instructions
- Preheat the oven to 350°F. Prepare 24 wells of a muffin tin by spraying with cooking spray.
- In a large bowl, mix together the pineapple juice, yellow cake mix, oil, and eggs until well blended.
- Cut each of the pineapple rings into four equal-sized pieces. Mix together the butter and brown sugar, and add about 1 teaspoon of the butter mixture to each well of the muffin tin. Add two pieces of pineapple and a maraschino cherry half, cut side up.
- Pour the cake batter into the muffin tins, filling to about ¼ inch from the top. Bake 20-25 minutes or until golden brown. Remove from oven and let cool 15 minutes, then loosen the cupcakes from the sides of the muffin tin with a knife and invert onto a cooling rack.
- Serve warm with freshly whipped cream, if desired.
Video
Nutrition
Nutrition information is automatically calculated, so should only be used as an approximation.
adapted from Betty Crocker
Are these baked in standard muffin tins or miniature ones that have 24 wells? Thank you.
They are baked in standard muffin tins. 🙂
GREAT!!! GREAT!!! GREAT !!!
Made these for a ladies tea for my wife’s work. They were a huge hit. So good. And pretty simple. I was very happy with how easy they came out of the pans. I did use pineapple tidbits, but otherwise, followed the recipe. Thank you so much.
I’m so glad to hear they were a hit!! Thanks for giving the recipe a try!
Wonderful recipe. So much easier to send home with adult son’s. After they come for dinner.
Very good, very quick recipe. Less than an hour from start to finish. Love it.
I’m so happy to hear that!!
This recipe was so very easy and uncomplicated, Thank you Lil’Luna!!!
I just took mines out of the oven, can’t wait to have one!!!!!
You’re welcome!! Hope you enjoyed the cupcakes!
Can these be made 2 days ahead & kept in the fridge?
Yes! Just store in an airtight container.
I want to try these today. I have 15.25 oz boxes of cake mix. Is that what you used?
Yep, that should work great!
A very tasty treat that everyone enjoyed more than a whole cake. They already gone before I remembered to take a picture. Lol
Haha..that’s what I love to hear! Thank you!
Okay I am terrified of cake, it always ends up horrible even from box mixes, but this recipe was so easy and ended up so delicious and tender!! The flipped out clean, they’re moist and sweet and have that perfect pineapple summer Tang. My family is anti MARACHINO cherry SO we threw a pecan in the middle and iT was amazing. Definitely going to be making these over and over this summer. Thank you!!
This makes me so happy to hear! Thank you so much for letting me know 🙂 Adding a pecan would be perfect!
This was a hit at iur home especi with the little one and bog ones with a sweet tooth
I love to hear that!! I am so glad they liked them! Thank you so much 🙂