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Pineapple Upside Down Sugar Cookies

A delightful twist on a classic dessert, these cookies combine a light, chewy base with sweet crushed pineapple and brown sugar for a refreshing summer treat.
Servings 12 cookies
Prep Time 15 minutes
Cook Time 20 minutes
Total Time 35 minutes

Ingredients

Cookie Base

  • 1 cup unsalted butter, softened At room temperature for easier mixing
  • 1 cup granulated sugar For sweetness and quick energy
  • 1 large egg At room temperature
  • 1 teaspoon vanilla extract For flavor
  • 2 cups all-purpose flour Scoop measured for best results
  • 1 teaspoon baking soda For leavening
  • 1/2 teaspoon salt To balance flavors
  • 1 cup crushed pineapple, drained Drain thoroughly to avoid excess moisture
  • 1/2 cup brown sugar For a caramel-like flavor

Topping

  • 12 pieces maraschino cherries, drained For decoration

Instructions

Preparation

  • Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
  • In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
  • Add the egg and vanilla extract, and mix well until combined.
  • In another bowl, whisk together the flour, baking soda, and salt until evenly mixed.
  • Gradually add the dry ingredients to the wet mixture, mixing until everything is just combined.
  • Fold in the crushed pineapple and brown sugar gently to incorporate them into the batter.

Baking

  • Spread the batter evenly on the prepared baking sheet, smoothing it out to make a nice, even layer.
  • Place the maraschino cherries on top of the batter, spacing them out as desired.
  • Bake for 15-20 minutes or until a toothpick inserted into the center comes out clean. Keep an eye on them to avoid overbaking.
  • Allow to cool before cutting into bars and serving.

Notes

Store in an airtight container at room temperature for 3-5 days. For longer storage, freeze wrapped cookies for up to 3 months. Thaw at room temperature before enjoying.
Calories: 150kcal
Course: Dessert, Snack
Cuisine: American
Keyword: Baking, Pineapple Dessert, Pineapple Upside Down Cookies, Sugar Cookies, Summer Treats