Pineapple Upside Down Cupcakes

2016-06-25 04.43.31 I don’t ever want to bake professionally, but I frequently am asked to bake for events that friends and coworkers are having. A coworker is having a 1920’s themed event in a few weeks and wanted to serve a 1920’s dessert. Pineapple upside down cake originated in 1925, so these cupcakes should be absolutely perfect!
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I had never made a pineapple upside down cake before and hadn’t eaten one in years, so I wasn’t really sure what to expect with these. My expectations were exceeded about a thousand times. These were absolutely amazing, and Graham said it was the best pineapple upside down cake he had ever had.

Typically this cake is made with a ring of pineapple & a cherry baked with the cake. I don’t like cherries, so I decided to make it a garnish instead of part of the cake. Also, this cake doesn’t come with a frosting of any sort. I personally don’t think something can be called a cake without a fluffy topping. I made a super fast & easy whipped cream frosting that was absolutely incredible on these (and out of the bowl with a spoon).

I can’t wait to make these again, and I hope my coworker & her guests love these as much as we did.

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Pineapple Upside Down Cupcakes 
Makes 12 cupcakes
(Recipe adapted from this one.)


  • 1 20 oz can of pineapple chunks (reserve the juice) 
  • 1/3 cup packed light brown sugar  
  • 1/3 cup unsalted butter, melted
  • 1 cup all-purpose flour
  • 3/4 cup sugar
  • 1/2 teaspoons baking powder
  • 1/2 stick unsalted butter, at room temperature
  • 1/2 cup pineapple juice
  • 1 egg  
  • 1 t. of coconut extract
  • 12 Maraschino cherries
  • Whipped cream frosting (recipe to follow)


  1. Preheat the oven to 350°F. Spray or grease a nonstick muffin pan. 
  2.  Drain the pineapple chunks, reserving 1/2 cup juice for the batter.
  3. Place the pineapple on a 2-3 sheets of paper towels to drain completely.
  4. Melt butter in a small sauce pan or microwave safe bowl.
  5. Mix together the brown sugar and melted butter. Divide evenly among the muffin pan cups (about 1 T. per cup).
  6. Arrange the pineapple chunks on top of the sugar mixture (about 4 per cup). Set aside.
  7. In the bowl of a mixer, or a large mixing bowl if using a hand mixer, combine the flour, sugar, and baking powder. Mix in the butter and pineapple juice, beating for 2 minutes or until smooth.
  8. Beat in the egg & the coconut extract.
  9. Spoon the batter over the fruit in the muffin pan.
  10. Bake on the middle rack for 30 minutes, or until a cake tester or toothpick inserted into the center of a cupcake comes out clean.
  11. Cool the cupcakes in the pan for 5 minutes, then place a wire rack on top of the muffin pan and flip the pan over so the pineapple is on top. Let cool completely before topping with whipped cream.

Whipped Cream Frosting


  • 1/2 pint of heavy whipping cream
  • 1/2 cup of powdered sugar


  1. In a large mixing bowl (or bowl of a stand mixer) beat whipping cream with a whisk or whisk attachment until stiff peaks form.
  2. Mix in the powdered sugar.

Pipe the whipped cream onto cupcakes & top with a cherry. Enjoy!

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4 thoughts on “Pineapple Upside Down Cupcakes

  1. Alicia Curley says:

    Hi! Found your blog through #healthySELF – I LOOOVE these cupcakes! Pineapple upside down cake is such an indulging pleasure for me – I like that these are single servings, so hopefully I won't go too crazy next time 🙂

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