This website may contain affiliate links and advertising so that we can provide recipes to you. Read my disclosure policy.
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!
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.
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).
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!
Pin this now to find it later
Pin It
Pineapple Upside-Down Cupcakes
Ingredients
Topping
- 6 tablespoons melted butter
- ¾ cup brown sugar
- 1 (20-ounce) can +1 (8-ounce) can pineapple chunks in pineapple juice, or 28 ounces fresh chopped pineapple
- 12 maraschino cherries
Cupcakes
- ½ cup softened unsalted butter
- ¾ cup granulated sugar
- 2 eggs
- 1 teaspoon vanilla extract
- 1 ½ cups all-purpose flour
- 1 ½ teaspoons baking powder
- ¼ teaspoon salt
- ½ cup buttermilk
Instructions
Toppings
- Preheat oven to 350 degrees Fahrenheit and lightly spray a 12-count cupcake tin with non-stick baking spray.
- Evenly divide the 6 tablespoons melted butter into the bottom of each cupcake well. sprinkle the bottom of each cup with 1 tablespoon of the ¾ cup brown sugar.
- Lay 4 of the 1 (20-ounce) can +1 (8-ounce) can pineapple chunks in pineapple juice, in a flower pattern over butter and brown sugar in each cup. Press one of the 12 maraschino cherries into the center of each "flower". Set aside.
Cupcakes
- Using a hand mixer, whisk the ½ cup softened unsalted butter and ¾ cup granulated sugar in a medium-sized bowl until creamy and well combined.
- Add the 2 eggs, whisking one at a time until combined. Stir in the 1 teaspoon vanilla extract.
- In a separate bowl, whisk together 1 ½ cups all-purpose flour, 1 ½ teaspoons baking powder, and ¼ teaspoon salt.
- Alternate adding flour mixture and ½ cup buttermilk to the butter mixture, starting and ending with flour, using a spatula and mixing until just combined after each addition
- Evenly divide the cupcake batter into the prepared pan. The batter will be thick, so use a spoon to spread it evenly into each cupcake well. Fill each cupcake well to the top.
- Bake 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, use oven mitts as the tin will be very hot, keep the cooling rack pressed against the tin flip it over. Lift the muffin tin off the cooling rack and the cupcakes should release easily.
- Allow to cool before serving. These pineapple upside down cupcakes taste great served warm with vanilla ice cream!
Notes
Nutrition
Nutrition information is automatically calculated, so should only be used as an approximation.
You Might Also Like These Recipes!
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!
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. 😁