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Pineapple Upside Down Sugar Cookies

Bring the flavors of a classic pineapple upside down cake to your cookie tray with these irresistible Pineapple Upside Down Sugar Cookies. Featuring a soft, buttery sugar cookie topped with caramelized brown sugar, sweet pineapple, and a bright maraschino cherry, they’re perfect for holidays, bake sales, summer parties, and everyday dessert cravings. This easy dessert recipe is simple to make, family-friendly, and guaranteed to become one of your favorite cookie recipes.

  • Total Time: 40 minutes
  • Yield: 13 cookies 1x

Ingredients

Scale

For the Cookie Dough

  • 1 cup butter, softened
  • 1½ cups granulated sugar
  • 2 eggs
  • 2 teaspoons vanilla extract
  • ½ cup sour cream
  • 3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon baking soda
  • ½ teaspoon salt

For the Topping

  •  13 canned pineapple slices, drained
  • 13 maraschino cherries
  • ½ cup butter, melted
  • 1 cup packed light brown sugar

Instructions

  1. Preheat oven to 350°F (175°C) and lightly grease a muffin pan.
  2. Divide the melted butter evenly among the muffin cups.
  3. Sprinkle the brown sugar over the melted butter.
  4. Place a pineapple slice or trimmed pineapple piece into each cup.
  5. Add one maraschino cherry to the center of each pineapple slice.
  6. Cream together the softened butter and granulated sugar until light and fluffy.
  7. Beat in the eggs one at a time.
  8. Mix in the vanilla extract and sour cream.
  9. In a separate bowl, whisk together the flour, baking powder, baking soda, and salt.
  10. Gradually mix the dry ingredients into the wet ingredients until a soft dough forms.
  11. Scoop cookie dough over each pineapple slice and gently spread to cover.
  12. Bake for 18–22 minutes until lightly golden.
  13. Cool for about 5 minutes before carefully inverting onto a cooling rack.
  14. Allow the cookies to cool slightly before serving.

Notes

  • Thoroughly drain and pat dry the pineapple before assembling.
  • Invert the cookies while they’re still warm for the cleanest release.
  • Store leftovers in the refrigerator because of the fruit topping.
  • Author: Emmy Carter
  • Prep Time: 20 minutes
  • Cook Time: 20 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 13 cookies
  • Calories: 340 calories per cookie

Keywords: Pineapple Upside Down Sugar Cookies, pineapple cookies, upside down cookies, easy sugar cookies, pineapple dessert, caramel pineapple cookies, tropical cookies, homemade sugar cookies