Pineapple Upside-Down Cupcakes

Sweet and simple pineapple upside down-cupcakes made entirely from scratch (don’t worry, they’re easy!). With fluffy vanilla cupcake bases topped off with caramelized pineapple and maraschino cherries, these are a great new way to enjoy a classic recipe!

Easy, from-scratch, pineapple upside-down cupcakes on a cooling rack.

Hello again! Sam here from Sugar Spun Run, back with another sweet-tooth appeasing recipe for you today!

I’m something of a pineapple fiend. I love it on my pizza (any other pineapple pizza lovers out there?! I know it seems to be a love-it or hate-it kind of thing!), I’m a sucker for a great Pina Colada, and the ever-popular Pineapple Upside-Down Cake is one of my all-time favorite cake recipes. In fact, I love it so much that, in an effort to justify my constant need to have this cake on hand, I decided to make a miniature version (or rather, a dozen miniature versions!) and these pineapple upside-down cupcakes were born.

Easy, from-scratch, pineapple upside-down cupcake on a plate.

I actually recently shared a full-sized pineapple upside-down cake recipe on my own site (because I’m obsessed, remember?), and decided that a miniature version was urgently necessary. A few tweaks were in order, though.

While the cupcakes are a very basic and simple vanilla cake recipe, I used buttermilk in this recipe to help keep them extra soft and keep them from drying out in their cupcake wells (and if you don’t happen to keep buttermilk handy – I know I rarely do – I have a super simple buttermilk substitute you can use that works just as well).

Easy, from-scratch, pineapple upside-down cupcake with a bite out to show the inside of this moist cake.

My biggest frustration with this recipe was that a 20 oz can of pineapple chunks is just too small to cover 12 cupcakes, so you’ll have to buy an additional small can of pineapples for that twelfth cupcake, leaving you with a few extra unused pineapple chunks. Alternatively you can still use the butter, brown sugar, and cherries but leave the pineapple off to avoid breaking open another can, which is what I usually do (as much as I love pineapple, I’m not going to turn down a brown sugar and cherry topped cupcake, either).

Other than that, these pineapple upside-down cupcakes are frustration-free! The vanilla cupcake base is simple, soft, and so fresh (better than any box-mix, trust me!). You can have them in your oven and baking in less than 25 minutes.

So…. what are you waiting for!? Enjoy!

Easy, from-scratch, pineapple upside-down cupcakes on a cooling rack in rows.

Pineapple Upside-Down Cupcakes

4.72 from 7 votes
Prep Time 25 minutes
Cook Time 25 minutes
Servings 12 *
Sweet and simple pineapple upside down-cupcakes made entirely from scratch (don’t worry, they’re easy!).



  • 6 Tablespoons butter melted
  • 3/4 cup brown sugar
  • 20 oz +8 oz can pineapple chunks in pineapple juice or substitute fresh pineapple
  • 12 Maraschino cherries


  • 1/2 cup unsalted butter softened to room temperature
  • 3/4 cup sugar
  • 2 eggs
  • 1 teaspoon vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup buttermilk


  1. Preheat oven to 350F and lightly spray a 12-count cupcake tin with baking spray.
  2. Evenly divide butter into the bottom of each cupcake well.
  3. Sprinkle each well with 1 Tablespoon of brown sugar.
  4. Rim the bottom of each pan by laying 4 pineapple chunks in a flower pattern over the butter and brown sugar.
  5. Press a Maraschino cherry into the center of each "flower". Set aside.


  1. Prepare your cupcakes by beating together butter and sugar in a medium-sized bowl until creamy and well-combined.
  2. Add eggs, beating one at a time until combined.
  3. Stir in vanilla extract.
  4. In a separate bowl, whisk together flour, baking powder, and salt.
  5. Alternate adding flour and buttermilk, starting and ending with flour and mixing until just combined after each addition (I prefer to do this part by hand with a spatula to be sure not to over-mix).
  6. Evenly divide the cupcake batter into your prepared pan. The batter will be thick, so use a spoon to spread it evenly into each cupcake well. Fill each cupcake well all the way to the top.
  7. Bake on 350F for 22-25 minutes.
  8. Remove, allow to cool for 5 minutes, and then place a wire cooling rack over the cupcake tin, covering each cupcake.
  9. Carefully, using potholders as the tin will be very hot, keep the cooling rack pressed against the tin and invert. Lift the muffin tin, the cupcakes should release easily.
  10. Allow to cool before serving. These pineapple upside down cupcakes taste great served warm with vanilla ice cream!

Recipe Notes

*This recipe can easily be doubled for 24 cupcakes

Nutrition Facts
Pineapple Upside-Down Cupcakes
Amount Per Serving
Calories 302 Calories from Fat 135
% Daily Value*
Fat 15g23%
Saturated Fat 9g45%
Cholesterol 64mg21%
Sodium 125mg5%
Potassium 109mg3%
Carbohydrates 41g14%
Fiber 1g4%
Sugar 28g31%
Protein 3g6%
Vitamin A 465IU9%
Calcium 58mg6%
Iron 1mg6%
* Percent Daily Values are based on a 2000 calorie diet.

All nutritional information is based on third party calculations and is only an estimate. Each recipe and nutritional value will vary depending on the brands you use, measuring methods and portion sizes per household.


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Samantha Merritt

Sam is the baker behind the website Sugar Spun Run, where she shares sweet, simple, and from-scratch dessert recipes (usually of the chocolate variety!). She lives in Pennsylvania with her husband and their two dogs, Penny and Leia.

Read More Posts by Samantha

Visit Samantha's Website

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  1. What is the difference between all purpose flour and self rising flour can you use either in recipes that call for one or the other i used all purpose in some biscuits and it didnt rise

  2. 5 stars
    I made these last weekend and they tasted AMAZING!! If the cupcakes weren’t for a cake walk, I would have eaten them all! Thanks for sharing this recipe!

  3. 5 stars
    I made this with a few tweaks, but it was AMAZING. I can’t believe I’ve never thought to make these before. Sweet, soft, moist, and sturdy; the perfect pineapple upside down experience.
    1/2 cup buttermilk –> 1/4 cup reserved pineapple juice, 1/4 cup buttermilk
    6 tbsp melted butter–> 6 tbsp softened butter, smeared around the bottom and sides of each cup
    3/4 cup brown sugar–> 1/4 tsp white sugar under the 1 tbsp brown sugar. Packed along the bottom and up sides of the tin.

    Thanks for a great recipe!

  4. 5 stars
    I just made the recipe using fresh pineapple. I didn’t have any buttermilk so I did 1/2 milk and 1/2 greek yogurt. They were amazing! They were easy to release from the pan, moist and delicious. I’m saving this recipe 🙂

  5. Question before making… can I use cupcake liners? Can they be paper or should I use the foil ones? I’d like to make these for my niece in laws birthday. Thanks

  6. 4 stars
    I liked this recipe. However, I added about a 1/3 cup of pineapple juice to the batter and I felt it enhanced the cupcakes! I didn’t change anything else /portions of dry vs liquid and they turned out great.

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