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Pineapple Upside Sugar Cookies

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  • Author: Sue
  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Total Time: 30 minutes
  • Yield: 12 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

These pineapple upside sugar cookies combine the fruity, caramelized magic of pineapple upside-down cake with the soft, chewy goodness of a sugar cookie. With bright pineapple, maraschino cherries, and a buttery base, these bite-sized treats are tropical, nostalgic, and guaranteed to impress.


Ingredients

  • 1/2 cup unsalted butter, softened
  • 3/4 cup granulated sugar
  • 1 egg
  • 1 tsp vanilla extract
  • 1 1/4 cups all-purpose flour
  • 1/2 tsp baking powder
  • 1/4 tsp salt
  • 6 canned pineapple rings, cut into small chunks
  • 6 maraschino cherries, halved
  • 1/4 cup brown sugar
  • Optional: 1–2 tsp pineapple juice (for extra flavor)

Instructions

  1. Preheat oven to 350°F (175°C). Lightly grease a standard muffin tin.
  2. Place 1 tsp brown sugar into the bottom of each muffin cup. Add a pineapple chunk and a cherry half, cut-side down.
  3. In a bowl, cream the butter and granulated sugar until light and fluffy.
  4. Beat in the egg and vanilla extract. Add pineapple juice if using.
  5. In a separate bowl, whisk together flour, baking powder, and salt. Gradually add to the wet ingredients to form a soft dough.
  6. Scoop and gently press dough over the fruit in each muffin cup, covering evenly.
  7. Bake for 12–15 minutes, until edges are golden and centers are set.
  8. Let cool in the pan for 5 minutes, then invert onto a tray to release the cookies.
  9. Cool completely before serving.

Notes

  • Pat pineapple chunks dry before using to avoid soggy cookies.
  • Add coconut extract or shredded coconut for a tropical twist.
  • Store-bought sugar cookie dough works in a pinch—just enhance it with vanilla or pineapple juice.
  • Dough can be made ahead and refrigerated for easier shaping.