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Pineapple Upside Down Sugar Cookies

These cookies combine the nostalgic flavors of the classic dessert with a delightful twist, featuring a chewy texture and a sweet caramelized pineapple topping.
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Prep Time 15 minutes
Cook Time 12 minutes
Total Time 27 minutes
Servings: 24 cookies
Course: Dessert
Cuisine: American
Calories: 120
Ingredients Equipment Method Notes

Ingredients
  

Main
  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 cup brown sugar packed
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 3 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1 teaspoon salt
  • 1 can 20 oz crushed pineapple, drained
  • 1/2 cup maraschino cherries halved

Equipment

  • Baking sheet
  • Mixing bowl
  • Whisk
  • Rubber spatula
  • Measuring cups and spoons
  • Parchment paper

Method
 

  1. Preheat the oven to 350°F (175°C).
  2. Line a baking sheet with parchment paper.
  3. In a mixing bowl, beat the softened butter, granulated sugar, and brown sugar together until creamy.
  4. Mix in the eggs and vanilla extract until fully combined.
  5. In another bowl, whisk together the flour, baking soda, and salt.
  6. Gradually add the dry ingredients to the wet mixture, mixing until just combined.
  7. In a small bowl, mix the drained crushed pineapple with halved maraschino cherries.
  8. Drop spoonfuls of cookie dough onto the prepared baking sheet, then place a spoonful of pineapple and cherry mixture on top.
  9. Bake for 10-12 minutes until the edges are golden.
  10. Let the cookies cool on the baking sheet for a few minutes before transferring them to a wire rack.

Notes

These cookies are best enjoyed fresh from the oven, but they can also be stored in an airtight container.