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Pineapple Upside Sugar Cookies

Pineapple Upside Sugar Cookies

These Pineapple Upside Sugar Cookies combine the nostalgic flavors of pineapple upside-down cake with a soft, chewy sugar cookie base. With crushed pineapple, coconut, and a caramelized brown sugar coating, they’re a tropical twist perfect for sunny days, bake sales, or festive treats.
Prep Time 15 minutes
Cook Time 15 minutes
Servings 24 cookies
Calories 180 kcal

Ingredients
  

  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • cups all-purpose flour
  • ½ teaspoon baking powder
  • ¼ teaspoon salt
  • ½ cup crushed pineapple well-drained
  • ½ cup brown sugar for rolling
  • ¼ cup unsweetened shredded coconut
  • Maraschino cherries optional, for garnish

Instructions
 

  • Preheat oven to 350°F (175°C). Line two baking sheets with parchment paper.
  • In a large bowl, cream butter and sugar until light and fluffy (2–3 minutes).
  • Beat in egg and vanilla until smooth.
  • In another bowl, whisk flour, baking powder, and salt.
  • Gradually mix dry ingredients into wet until just combined.
  • Fold in drained pineapple and shredded coconut.
  • In a small bowl, mix brown sugar with 1–2 teaspoon flour.
  • Roll dough into tablespoon-sized balls and coat in brown sugar mixture.
  • Place on baking sheets, flatten slightly, and add a maraschino cherry to each (if using).
  • Bake for 12–15 minutes, until edges are golden.
  • Cool on sheet for 5 minutes, then transfer to wire rack to cool completely.

Notes

  • Drain pineapple well to avoid soggy dough.
  • Substitute lime zest for a citrusy boost.
  • For crunch, toast the coconut beforehand.
  • Freeze dough balls for later; bake from frozen with 1–2 extra minutes.
  • For a decorative finish, drizzle with pineapple glaze (powdered sugar + pineapple juice).