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+ servings
A stack of three Pineapple Upside Sugar Cookies, each topped with a pineapple ring and a maraschino cherry.

Pineapple Upside Down Sugar Cookies

These cookies combine the sweet, tropical flavor of pineapple upside down cake with the simple joy of a sugar cookie.
Prep Time 20 minutes
Cook Time 10 minutes
Chilling Time 15 minutes
Total Time 45 minutes
Servings: 24 cookies
Course: Cookies, Dessert
Cuisine: American

Ingredients
  

For the Cookies
  • 1 cup unsalted butter softened
  • 1.5 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 3 cup all-purpose flour
  • 1 teaspoon baking powder
  • 0.5 teaspoon salt
For the Topping
  • 1 can crushed pineapple drained well
  • 0.5 cup brown sugar packed
  • 0.25 cup maraschino cherries halved

Equipment

  • Baking sheets
  • Parchment paper
  • Mixing bowls
  • Electric mixer
  • Rolling Pin
  • cookie cutters

Method
 

  1. In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
  2. Beat in the eggs one at a time, then stir in the vanilla extract.
  3. In a separate bowl, whisk together the flour, baking powder, and salt.
  4. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix.
  5. Divide the dough in half, flatten each half into a disc, wrap in plastic wrap, and refrigerate for at least 15 minutes.
  6. Preheat your oven to 375°F (190°C). Line baking sheets with parchment paper.
  7. On a lightly floured surface, roll out one disc of dough to about 1/4-inch thickness.
  8. Use cookie cutters to cut out shapes. Place the cut-out cookies onto the prepared baking sheets.
  9. In a small bowl, combine the drained crushed pineapple and packed brown sugar. Mix well.
  10. Place a small spoonful of the pineapple mixture onto the center of each cookie. Top with a maraschino cherry half.
  11. Bake for 10-12 minutes, or until the edges are lightly golden brown.
  12. Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Notes

You can also make these cookies by pressing the dough into small tart pans or muffin tins, adding the pineapple topping, and baking. Adjust baking time as needed.

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