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Pineapple Upside Sugar Cookies

Pineapple Upside Sugar Cookies

Delicious sugar cookies with a caramelized pineapple and cherry topping, reminiscent of classic pineapple upside-down cake.

  • Total Time: 1 hour 32 minutes
  • Yield: 24 cookies 1x

Ingredients

Scale
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 tsp vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1/2 tsp baking powder
  • 1/4 tsp salt
  • 1/2 cup crushed pineapple, well-drained
  • 1/4 cup brown sugar
  • Maraschino cherries, halved
  • Pineapple slices or tidbits (optional for topping)

Instructions

  1. Prepare the Dough: In a large mixing bowl, cream together the softened butter and granulated sugar using an electric mixer on medium speed until light and fluffy (about 2-3 minutes).
  2. Add Wet Ingredients: Beat in the egg and vanilla extract until fully combined.
  3. Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, mixing on low speed until a soft dough forms.
  4. Fold in Pineapple: Gently fold in the well-drained crushed pineapple. Be sure to remove as much moisture as possible from the pineapple to prevent the dough from becoming too wet. Pat the pineapple dry with paper towels if needed.
  5. Chill the Dough: Cover the dough and refrigerate for at least 1 hour. This helps the dough firm up, making it easier to handle and bake evenly.
  6. Prepare Toppings: While the dough chills, prepare a small bowl of brown sugar. This will create the “upside-down” caramelized effect.
  7. Assemble Cookies: Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper. Scoop about 1.5 tablespoons of dough and roll it into a ball. Flatten each ball slightly and press the top into the brown sugar.
  8. Add Pineapple & Cherry: Optionally, press a small pineapple tidbit or a slice piece into the center of each cookie. Add half a maraschino cherry on top of the pineapple for that classic upside-down look.
  9. Bake: Place the cookies brown sugar side up on the prepared baking sheet, spacing them about 2 inches apart. Bake for 10-12 minutes or until the edges are lightly golden.
  10. Cool & Serve: Let the cookies cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.

Notes

  • Ensure your crushed pineapple is very well-drained to prevent soggy cookies.
  • For an extra caramelized topping, you can broil the cookies for an additional 1-2 minutes after baking — just watch closely to prevent burning.
  • Author: Sabrine Jay
  • Prep Time: 20 minutes
  • Cook Time: 12 minutes
  • Category: Dessert, Cookie
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 150

Keywords: pineapple, sugar cookies, upside-down, cherry, dessert