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Upside Sugar Cookies Recipe

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4.1 from 154 reviews

Delight in these charming Upside Sugar Cookies featuring a soft, buttery cookie base topped with juicy canned pineapple rings and a sparkling sugar finish. Perfectly baked until golden at the edges, these cookies combine sweet tropical flavors with classic sugar cookie goodness for a unique treat.

  • Total Time: 29 minutes
  • Yield: 12 servings

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

  • 10–12 canned pineapple rings, well-drained and patted dry
  • Additional sugar for sprinkling

Instructions

  1. Preheat Oven: Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper to prevent sticking and ease cleanup.
  2. Cream Butter and Sugar: In a large bowl, beat together the softened unsalted butter and granulated sugar until the mixture becomes light and fluffy, setting the base for a tender cookie.
  3. Add Egg and Vanilla: Incorporate the egg and vanilla extract, mixing thoroughly until well combined to enrich the dough with flavor and moisture.
  4. Mix Dry Ingredients: In a separate bowl, whisk the all-purpose flour, baking soda, and salt, then gradually add these dry ingredients to the wet butter mixture to form a soft and manageable dough.
  5. Shape Dough Balls: Roll the dough into balls roughly 1½ tablespoons in size, flatten them slightly, and arrange evenly spaced on the prepared baking sheets.
  6. Add Pineapple Rings: Place one well-drained and patted dry canned pineapple ring on top of each dough disk, pressing gently to adhere but preserve shape.
  7. Sprinkle Sugar: Sprinkle additional granulated sugar on top of the pineapple rings to add extra sparkle and sweetness after baking.
  8. Bake Cookies: Bake the cookies for 12–14 minutes, or until the edges are just golden, indicating they’re perfectly baked without over-drying.
  9. Cool and Serve: Let the cookies cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely and set.

Notes

  • Make sure the pineapple rings are well drained and patted dry to avoid soggy cookies.
  • Use parchment paper or silicone baking mats to prevent sticking and promote even baking.
  • For chewier cookies, slightly underbake and allow to cool on the sheet.
  • Feel free to experiment by adding a sprinkle of cinnamon or nutmeg to the dough for a warm spice variation.
  • Store cookies in an airtight container at room temperature for up to 5 days.
  • Author: Olivia
  • Prep Time: 10 minutes
  • Cook Time: 14 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American