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Pineapple Upside Down Sugar Cookies


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  • Total Time: 29 minutes
  • Yield: 24 cookies
  • Diet: Vegetarian

Description

These portable cookies combine the tropical flavors of pineapple upside-down cake with the classic taste of sugar cookies, featuring a caramelized pineapple ring topping.


Ingredients

  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend)
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 can canned pineapple rings (well-drained)
  • 2 tablespoons additional sugar for sprinkling


Instructions

  1. Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone mats and set aside.
  2. Drain the canned pineapple rings very well. Pat them dry with paper towels and cut them into halves or quarters if you prefer smaller cookie toppers.
  3. Cream together the softened unsalted butter and 1 cup granulated sugar until light and fluffy—about 2–3 minutes with an electric mixer on medium speed.
  4. Beat in the large egg and 1 teaspoon vanilla extract (if using) until combined.
  5. Whisk together the 2 cups all-purpose flour, 1 teaspoon baking soda, and 1/2 teaspoon salt in a separate bowl.
  6. Add the dry ingredients to the wet mixture gradually, mixing on low speed until a soft dough forms.
  7. Use a 1.5 tablespoon cookie scoop and place the dough balls about 2 inches apart on the prepared baking sheets.
  8. Flatten each dough ball gently with the palm of your hand to create a small well in the center.
  9. Place a well-drained pineapple ring piece on top of each flattened dough portion. Sprinkle each pineapple-topped cookie lightly with the additional sugar.
  10. Bake for 10–14 minutes, rotating the baking sheets halfway through, until cookies are golden.
  11. Allow cookies to cool on the baking sheet for 3–5 minutes before transferring to a wire rack to cool completely.

Notes

Ensure pineapple is thoroughly drained to avoid soggy cookies. Use room temperature ingredients for better mixing.

  • Prep Time: 15 minutes
  • Cook Time: 14 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American