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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.

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Pineapple Upside-Down Cupcakes

4.70 from 13 votes
Sweet and simple pineapple upside down-cupcakes made entirely from scratch (don’t worry, they’re easy!).
Prep Time: 25 minutes
Cook Time: 25 minutes
Servings: 12 *





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


  • Prepare your cupcakes by beating together butter and sugar in a medium-sized bowl until creamy and well-combined.
  • Add eggs, beating one at a time until combined.
  • Stir in vanilla extract.
  • In a separate bowl, whisk together flour, baking powder, and salt.
  • 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).
  • 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.
  • Bake on 350F for 22-25 minutes.
  • Remove, allow to cool for 5 minutes, and then place a wire cooling rack over the cupcake tin, covering each cupcake.
  • 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.
  • Allow to cool before serving. These pineapple upside down cupcakes taste great served warm with vanilla ice cream!


*This recipe can easily be doubled for 24 cupcakes


Calories: 302kcalCarbohydrates: 41gProtein: 3gFat: 15gSaturated Fat: 9gCholesterol: 64mgSodium: 125mgPotassium: 109mgFiber: 1gSugar: 28gVitamin A: 465IUCalcium: 58mgIron: 1mg

Nutrition information is automatically calculated, so should only be used as an approximation.

Tried this recipe?Mention @alyssa_therecipecritic or tag #therecipecritic!


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About 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.

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Recipe Rating


  1. 3 stars
    The recipe was super easy, but the butter bubbled over and started a fire in my oven! The cupcakes had 10 minutes left to bake. Hoping to finish baking them after I scour the oven down. 🙁 Maybe less melted butter in the bottom of the cupcakes next time? I definitely want this to work!

  2. 5 stars
    This is a wonderful recipe! I followed recipe to the T. The cupcakes came beautifully. No overflow on the cupcake pan, perfect golden color.. And the taste was on point, moist cake with perfect consistancy. I will definitely make them again. Wish I could post a picture of them. 😁