Pineapple Upside Down Cupcakes are the cutest little twist on the classic cake, and they are always a hit! Each one has that buttery brown sugar topping, sweet pineapple, and a bright cherry right in the center, all baked into perfectly portioned cupcakes.
What makes these so great is how easy they are, thanks to a cake mix shortcut, but they still look like you spent a lot of time in the kitchen. They are perfect for parties, potlucks, holidays, or anytime you want a fun dessert that serves itself.
If you love easy, nostalgic desserts like this, you should also try Pineapple Upside Down Cake, Strawberry Shortcake Bars, and Lemon Bars.
Why we think you’ll love it:
- Shortcut friendly. Starts with a cake mix, so you can make a homemade style dessert with very little prep time.
- Perfect for gatherings. Individual cupcakes are easy to serve at parties, potlucks, or family dinners.
- Reliable results. This tested recipe turns out soft, moist cupcakes that look impressive but are simple to make.
Pineapple Upside Down Cupcake Ingredients
- Pineapple rings (1 twenty ounce can, drained and juice reserved): Adds juicy sweetness and that signature tropical flavor. The reserved juice is used in the batter for extra moisture and flavor.
- Yellow cake mix (1 fifteen point twenty five ounce box): Creates a soft, fluffy cupcake base with consistent results. We like classic brands like Betty Crocker or Duncan Hines. Pineapple cake mix can also be used.
- Vegetable oil (½ cup): Keeps the cupcakes moist and tender even after they cool. You can substitute canola oil if needed.
- Eggs (3): Provides structure and richness, helping the cupcakes rise properly and hold their shape.
- Butter melted (⅓ cup): Combines with brown sugar to form the caramelized topping that gives these cupcakes their classic upside down flavor.
- Brown sugar packed (⅔ cup): Adds deep sweetness and creates that gooey, buttery glaze as the cupcakes bake. Light or dark brown sugar both work.
- Maraschino cherries (12, cut in half): Brings bright color and a sweet pop of flavor that makes each cupcake feel festive and fun.
How to Make Pineapple Upside Down Cupcakes
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 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.
Kristyn’s Recipe Tips
- Spray the muffin tin very well to help the caramel topping release cleanly after baking.
- 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 be equal to 1 cup. If you are shy, add water to the juice to get 1 cup.
- 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.
- Do not overfill the wells since the cupcakes will rise and could spill over.
- Let cupcakes cool slightly before inverting so the topping sets but is still warm enough to release.
Pineapple Upside Down Cupcakes Recipe
Video
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
- ⅓ cup butter melted
- ⅔ 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.
Notes
- Do not overfill the wells since the cupcakes will rise and could spill over.
- Let cupcakes cool slightly before inverting so the topping sets but is still warm enough to release.
- Use kitchen shears to quickly cut pineapple rings into even pieces for easier assembly.
- 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 be equal to 1 cup. If you are shy, add water to the juice to get 1 cup.
Nutrition
Nutrition information is automatically calculated, so should only be used as an approximation.
Recipe FAQ
Store the pineapple upside down cake cupcakes in the fridge, in an airtight container, for about 3 days.
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.
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This recipe was first shared April, 2016.
Very, very good! Really outstanding! But, can you freeze them? Only my husband and myself at home would like to freeze them?
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 🙂
I love that these are cupcakes. so BEAUTIFUL and tasty. Making these more this summer.
SUch a fun twist on a classic. Perfect for parties!
Was the muffin tin, the mini type or regular size?
Thank you
my daughter made these with her friends the other day! They turned out great!
My hubby loves these! I am more of the chocolate fan & him the fruity, but I really do like these! They are soft & full of flavor! I love pineapple, so if I can’t have chocolate, this is the next best!
Pineapple upside down cake made in a dutch oven is my moms favorite camping treat. With your delicious recipe and instructions im able to have it at home!
My husband can eat a whole upside down cake by himself. Excited to try these individual servings. Same great taSte.
These look absolutely fantastic. I made similar cupcakes for a church function last year and they went over very well. I used some crushed pineapple and some which had been cut into quarters (two to a muffin cup). 1/4 tsp butter, one tsp crushed pineapple, 1/2 cherry then fill each cup to about 1/4 inch from top.
That sounds great! I bet they were a hit 🙂
Must have been. I’ve been volunteered to make more this year (+ 3 additional cakes) for their bake sale
Super delicious and so cute!! Perfect for a party. Thanks for the recipe!!
They’re perfect for parties!! Hope you give them a try:) Let me know what you think!
Such cute little cakes!
Aren’t they!:) Thanks so much for checking them out!
Nice recipes Kristyn. Thank you and have a great Monday.