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Pineapple Upside Down Sugar Cookies

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A delightful twist on the classic dessert, featuring buttery sugar cookies topped with a glossy, caramelized pineapple ring for a crispy and tender treat.

  • Total Time: 29 minutes
  • Yield: 12 servings 1x

Ingredients

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

Instructions

  1. Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
  2. In a large bowl, cream butter and sugar until light and fluffy.
  3. Beat in the egg and vanilla until well combined.
  4. In a separate bowl, whisk together flour, baking soda, and salt. Gradually add to the butter mixture to form a soft dough.
  5. Roll dough into 1½ tbsp balls, flatten slightly, and place on baking sheet.
  6. Top each dough disk with a pineapple ring, pressing gently.
  7. Sprinkle sugar on top of pineapple for extra sparkle.
  8. Bake for 12–14 minutes until edges are golden. Cool for 5 minutes, then transfer to a rack.

Notes

Ensure to drain and pat the pineapple rings thoroughly to avoid sogginess. Room-temperature butter works best for incorporating air into the dough.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 200
  • Sugar: 12g
  • Sodium: 150mg
  • Fat: 10g
  • Saturated Fat: 6g
  • Unsaturated Fat: 4g
  • Trans Fat: 0g
  • Carbohydrates: 24g
  • Fiber: 0g
  • Protein: 1g
  • Cholesterol: 25mg