Pineapple Upside-Down Cupcakes


It’s been a while since I’ve last baked in the kitchen. I had the baking bug recently and decided to make pineapple upside-down cupcakes. To be honest, I’ve never tried pineapple upside-down cake before! It’s my boyfriend’s favorite cake, so I thought, why not? I decided to make a cupcake version – easier to eat and share. The cupcakes turned out beautiful with a golden brown color and delicious with a wonderful brown sugar taste. Plus, I love the upside-down aspect of them. If you’re a fan of pineapple, this is the cake to try!



Pineapple Upside-Down Cupcakes Recipe (yields 24):

Ingredients for cake:

  • 2 sticks unsalted butter, softened
  • 1-1/2 cups granulated sugar
  • 1/2 cup packed brown sugar
  • 3 eggs
  • 2-1/2 cups all-purpose flour
  • 1 tsp baking powder
  • 1/2 tsp baking soda
  • 1/2 tsp salt
  • 1 tsp vanilla
  • 1 cup sour cream


Directions for cake:

  1. Preheat oven to 350 degrees
  2. Spray muffin pans with baking spray
  3. In medium bowl, whisk together dry ingredients: flour, baking powder, baking soda & salt
  4. In bowl of stand mixer, beat butter and sugars until light and fluffy
  5. Add eggs, one at a time, and beat until combined; add vanilla
  6. Add in half of the dry ingredients and mix, scraping sides of bowl
  7. Pour in sour cream and mix
  8. Add in the rest of the dry ingredients and mix until well combined


Ingredients for pineapple mixture:

  • 1/2 stick unsalted butter, melted
  • 1/2 cup packed brown sugar
  • 2 (8 oz.) cans crushed pineapple, drained
  • 1/2 cup chopped walnuts
  • 12 maraschino cherries, cut in half


Directions for pineapple mixture:

  1. In large bowl, mix melted butter and brown sugar
  2. Add pineapple and walnuts; mix well


To assemble cupcakes:

  1. Place half of a maraschino cherry (cut side up) in the center of prepared muffin pan
  2. Spoon thin layer of pineapple mixture around the cherry
  3. Place a scoop of cake batter on top, fill to rim
  4. Bake for 20-22 minutes until toothpick inserted in center comes out clean
  5. Let cupcakes cool in pans for about 10 minutes
  6. Run a knife around the cupcakes in the pan and then invert onto wire rack.



Jamie’s tips for this recipe:

  • Be sure to add the cake batter slowly into the muffin pan; otherwise, it might move the cherry off center.
  • If you don’t like pineapple, the cake batter itself makes delicious plain cupcakes on its own without the pineapple mixture. I had a little extra batter remaining and baked mini ones (no pineapple) and they were scrumptious when cooked a little longer to well done.
  • Add a scoop of ice cream for the perfect dessert!


Have you tried pineapple upside-down cake before?

About Jamie

Hi! My name is Jamie and I am a Boston native, amateur baker, food nerd, macaron addict, globetrotter, and fitness enthusiast. Currently, I manage grants at Dana-Farber Cancer Institute in Boston, MA. I'll be blogging every Friday about my baking endeavors, food interests and travel, restaurant reviews, and reports on the latest food trends.

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