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Pineapple Upside Down Sugar Cookies

If you’ve been searching for a dessert that combines the nostalgic charm of pineapple upside down cake with the convenience of cookies, these Pineapple Upside Down Sugar Cookies are a must-try. With a buttery, caramelized brown sugar topping and a soft sugar cookie base, these treats are perfect for parties, potlucks, or an everyday sweet indulgence.
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Prep Time 15 minutes
Cook Time 18 minutes
Total Time 33 minutes
Servings: 4 servings
Course: Dessert
Cuisine: American
Calories: 485
Ingredients Equipment Method Notes

Ingredients
  

For the Topping
  • 1/4 cup unsalted butter melted
  • 1/2 cup packed light brown sugar
  • 12 pineapple rings each cut into halves (canned or fresh)
  • 24 maraschino cherries drained
For the Sugar Cookie Base
  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon pure vanilla extract
  • 2.25 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon salt
  • 2 tablespoons pineapple juice from canned pineapple or fresh

Equipment

  • Muffin tin
  • Small bowl
  • Large mixing bowl
  • Electric mixer
  • Baking sheet or large platter

Method
 

  1. Preheat your oven to 350°F. Prepare your muffin tins by lightly greasing them or lining with paper liners.
  2. In a small bowl, combine 1/4 cup melted unsalted butter and 1/2 cup packed light brown sugar until well mixed. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup.
  3. Place half a pineapple ring into each muffin cup and nestle a maraschino cherry in the center to create the classic pineapple upside down look.
  4. In a large bowl, cream together 1 cup softened unsalted butter and 1 cup granulated sugar with an electric mixer until light and fluffy, about 2 minutes.
  5. Beat in 1 large egg, 1 teaspoon pure vanilla extract, and 2 tablespoons pineapple juice until well combined.
  6. In a separate bowl, whisk together 2.25 cups all-purpose flour, 1/2 teaspoon baking powder, 1/4 teaspoon baking soda, and 1/4 teaspoon salt.
  7. Gradually mix the dry ingredients into the wet ingredients just until incorporated, being careful not to overmix.
  8. Spoon the cookie dough over the prepared topping in each muffin cup, filling each about 2/3 full.
  9. Bake for 15-18 minutes, or until the edges are golden brown and the centers are set.
  10. Allow the cookies to cool in the pan for about 5 minutes. Then, place a baking sheet or large platter over the muffin tin and invert quickly to release the cookies.
  11. Let the cookies cool completely before serving so the caramelized topping has time to set.

Notes

These Pineapple Upside Down Sugar Cookies are a delightful twist on a classic dessert, combining a soft, buttery sugar cookie base with a caramelized pineapple and cherry topping. They are perfect for parties or casual gatherings, and most of the ingredients are common pantry staples. Feel free to experiment with variations such as substituting pineapple with peaches or adding a hint of coconut extract for an extra tropical flavor. Best enjoyed fresh, they will also keep in an airtight container for a few days.