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Pineapple Upside Down Sugar Cookie

Pineapple Upside Down Sugar Cookie

These pineapple upside down sugar cookies capture the nostalgic charm of a classic cake in soft, chewy cookie form, complete with juicy pineapple rings, sweet cherries, and a golden caramel glaze.

  • Total Time: 35 minutes
  • Yield: 12 cookies 1x

Ingredients

Scale
  • 2 ¼ cups all-purpose flour
  • 1 teaspoon baking powder
  • ½ teaspoon salt
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 12 pineapple rings (canned, drained and patted dry)
  • 12 maraschino cherries
  • ½ cup brown sugar (optional, for glaze)

Instructions

  1. Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper or grease a muffin tin.
  2. In a bowl, whisk together flour, baking powder, and salt.
  3. In another bowl, cream together butter and sugar until fluffy. Beat in eggs and vanilla extract.
  4. Gradually add dry ingredients to the wet mixture, stirring until combined.
  5. Scoop dough onto prepared baking sheet or into muffin cups.
  6. Top each dough scoop with a pineapple ring and place a cherry in the center.
  7. Brush the top with brown sugar syrup if using.
  8. Bake for 12 to 15 minutes, until edges are golden.
  9. Let cookies rest for 5 minutes before transferring to a cooling rack.

Notes

  • Pat the pineapple rings dry to prevent soggy cookies.
  • Use muffin tins for a perfectly shaped cookie with caramel edges.
  • Refrigerate dough slightly to help it hold its shape.
  • Author: Monica
  • Prep Time: 20 minutes
  • Cook Time: 15 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Nutrition

  • Serving Size: 1 cookie
  • Calories: 260
  • Sugar: 21g
  • Sodium: 95mg
  • Fat: 13g
  • Saturated Fat: 8g
  • Unsaturated Fat: 4g
  • Trans Fat: 0g
  • Carbohydrates: 33g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 45mg

Keywords: pineapple upside down cookies, sugar cookies, pineapple dessert, tropical cookie recipe, cherry topped cookies