January 25, 2017

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes: a sweet cake base topped with a brown sugar, pineapple and maraschino cherries.

Pineapple Upside Down Cupcakes by A Teaspoon of Home

This sweet dessert takes a classic dessert and turns it into individual portions. Pineapple upside down cake is a total blast from my past dessert. I don’t remember eating it often but anytime I did it was a real treat.

I love the combination of flavors from the sweet cake base to the rich pineapple topping. If you’re looking for something to change up the normal go to treats, this is the dessert for you.

These were a total success with my family. Every single member ate them and no one child spit any out. That right there is a major accomplishment.

Pineapple Upside Down Cupcakes by A Teaspoon of Home

Pineapple Upside Down Cupcakes


  • 1st Layer:
  • 1 (20 oz) can pineapple chunks in pineapple juice
  • 1/3 c packed brown sugar
  • 1/3 c butter, melted
  • Cupcake Layer:
  • 1 c flour
  • 3/4 c sugar
  • 1/2 t baking powder
  • 1/4 t salt
  • 1/4 c butter, softened
  • 1/2 c pineapple juice (from pineapple chunks can)
  • 1 egg
  • 1/2 t vanilla
  • Topping:
  • 3/4 c heavy cream
  • 2 T sugar
  • 12 maraschino cherries


  1. Preheat oven to 350 degrees.
  2. Spray 12 muffin cups generously with non-stick cooking spray.
  3. First Layer:
  4. Drain pineapple chunks but save the juice for the batter.
  5. Place pineapple over several layers of paper towels to drain well.
  6. Melt butter in a microwave safe bowl then stir brown sugar into melted butter.
  7. Divide mixture into muffin wells, adding about 2 t into each one.
  8. Arrange pineapple chunks on top of sugar mixture about 4 per well and set aside.
  9. Cupcake Layer:
  10. Mix dry ingredients into a bowl.
  11. Using a hand mixer, add butter and pineapple juice then mix until batter is smooth.
  12. Mix in egg and vanilla until well combined.
  13. Divide batter evenly among the muffin cups, layering over pineapple layer.
  14. Bake in preheated oven until center of cupcake comes out clean, about 23-26 minutes.
  15. Remove from oven and cool 5 minutes, then run a sharp knife around the edges to loosen.
  16. Place a wire cooling rack over the top of the muffin pan and flip to invert on wire rack.
  17. Let cool completely and then top with whipped cream and cherry just before serving.
  18. Topping:
  19. Using a hand mixer or whisk attachment, whip cream on high speed until soft peaks form.
  20. Add sugar then whip until stiff peaks form.
  21. Place on top of cupcake with a maraschino cherry.
  22. Recipe: cookingclassy.com

They are quite simple to create and they will disappear before you know it. My only suggestion is to make sure you generously grease the muffin tins. I had a few cupcakes that refused to come out and because the sugar caramelizes I had to use some serious skill to remove them. I didn’t end up with a full dozen, but every inch of the cupcakes were eaten.

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Pineapple Upside Down Cupcakes by A Teaspoon of Home

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