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

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 cupcakes


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 cupcakes

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

4.7 from 3 reviews
Pineapple Upside-Down Cupcakes
Sweet and simple pineapple upside down-cupcakes made entirely from scratch (don’t worry, they’re easy!).
Serves: 12*
  • 6 Tablespoons butter, melted
  • ¾ cup brown sugar
  • 20 oz +8 oz can pineapple chunks in pineapple juice (or substitute fresh pineapple)
  • 12 Maraschino cherries
  • ½ cup unsalted butter, softened to room temperature
  • ¾ cup sugar
  • 2 eggs
  • 1 teaspoon vanilla extract
  • 1½ cups all-purpose flour
  • 1½ teaspoons baking powder
  • ¼ teaspoon salt
  • ½ 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!
*This recipe can easily be doubled for 24 cupcakes
Nutrition Information
Calories: 335


You Might Also Like These Recipes!

Easy Vanilla Cupcakes

Lemon Blueberry Cupcakes

Lemon Blueberry Cupcakes

Carrot Cake Cupcakes

  • share the post!
  • read more posts in
    · · ·