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Pineapple Upside-Down Sugar Cookies Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.4 from 6 reviews
  • Author: Sue
  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Total Time: 30 minutes
  • Yield: 10-12 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Description

Pineapple Upside Sugar Cookies combine the tropical sweetness of canned pineapple rings with classic sugar cookies, baked to golden perfection with a delightful caramelized pineapple topping that adds a unique twist to the traditional cookie experience.


Ingredients

Cookie Dough

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 egg
  • 1 tsp vanilla extract
  • 2½ cups all-purpose flour
  • ½ tsp baking soda
  • ¼ tsp salt

Topping

  • 1012 canned pineapple rings, well-drained and patted dry
  • Additional sugar for sprinkling


Instructions

  1. Preheat Oven: Preheat your oven to 350°F (175°C) to prepare for baking the cookies.
  2. Prepare Pineapple: Drain canned pineapple rings thoroughly and pat dry to remove excess moisture to avoid soggy cookies.
  3. Make Cookie Dough: In a mixing bowl, cream together the softened unsalted butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until well combined.
  4. Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt.
  5. Mix Dry and Wet: Gradually add the dry ingredients to the wet ingredients, mixing until just combined to form a soft dough.
  6. Shape and Arrange Cookies: Take portions of the dough and flatten slightly. Place each cookie dough portion onto a lined or greased baking sheet, then carefully press one pineapple ring onto each cookie, sprinkling additional sugar on top of the pineapple for caramelization.
  7. Bake Cookies: Bake in the preheated oven for about 12-15 minutes or until the edges are golden and the cookies are set.
  8. Cool: Allow the cookies to cool on baking sheets for several minutes before transferring to wire racks to cool completely, allowing the pineapple topping to set.

Notes

  • Ensure pineapple rings are well-patted dry to prevent excess moisture from making the cookies soggy.
  • You can substitute brown sugar for the additional sugar topping for a richer caramel flavor.
  • Store cookies in an airtight container to maintain freshness for up to 4 days.
  • For a softer cookie, slightly underbake or reduce baking time by a minute or two.