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!
Pineapple Upside-Down Cupcakes
- 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
- 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
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