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Pineapple Upside-Down Sugar Cookies Recipe

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★★★★★

4.9 from 63 reviews

These Pineapple Upside-Down Sugar Cookies blend the classic tropical flavors of pineapple and cherry with a soft, buttery sugar cookie base. Featuring a delightful caramelized brown sugar and butter glaze topped with juicy pineapple slices and maraschino cherries, these cookies are a perfect balance of sweet and tangy. Easy to prepare and baked to golden perfection, they make a charming treat for any occasion.

Ingredients

Scale

Cookie Dough

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 ½ cups all-purpose flour
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ½ teaspoon salt

Topping

  • 1 can (8 oz) pineapple slices, drained (reserve juice)
  • ¼ cup unsalted butter
  • ½ cup brown sugar, packed
  • Maraschino cherries (one for each cookie)

Instructions

  1. Preheat Oven and Prepare Baking Sheets: Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper to prevent sticking and promote even baking.
  2. Cream Butter and Sugar: In a mixing bowl, cream the softened butter and granulated sugar together using an electric mixer until the mixture becomes light and fluffy, about 3-4 minutes, to incorporate air for a tender cookie.
  3. Add Egg and Vanilla: Beat in the egg and vanilla extract until the mixture is smooth and well combined, ensuring the flavors meld evenly throughout the dough.
  4. Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt to distribute the leavening agents and seasoning evenly.
  5. Mix Dry and Wet Ingredients: Gradually add the dry flour mixture to the creamed butter mixture, stirring gently until just combined to avoid overmixing which can make cookies tough.
  6. Make Brown Sugar Butter Mixture: In a small saucepan over medium heat, melt ¼ cup of unsalted butter with the brown sugar, stirring continuously until the mixture is bubbly and smooth, forming a caramel-like glaze.
  7. Assemble Toppings on Baking Sheets: Spoon about a tablespoon of the warm butter-sugar mixture onto the center of each cookie spot on the prepared baking sheets. Place a pineapple slice on top of each dollop, then position a maraschino cherry in the center of each pineapple slice.
  8. Top with Cookie Dough: Scoop about 1 tablespoon of cookie dough and gently spread it over each pineapple slice, making sure to cover the fruit slightly but leaving some visible for presentation.
  9. Bake the Cookies: Place the baking sheets in the preheated oven and bake for 12-15 minutes, or until the edges of the cookies are lightly golden brown, indicating they are cooked through.
  10. Cool Before Serving: Allow the cookies to cool on the baking sheets for 5 minutes to set, then transfer them to a wire rack to cool completely for best texture and handling.

Notes

  • Use room temperature butter for easier creaming with sugar.
  • Do not overmix the dough to keep cookies tender and soft.
  • Reserve the pineapple juice for another use, such as a cocktail or smoothie.
  • For a more tropical flavor, consider adding a teaspoon of coconut extract with the vanilla.
  • Store cookies in an airtight container at room temperature for up to 3 days.

Keywords: pineapple upside-down cookies, sugar cookies, tropical cookies, pineapple cherry cookies, baked cookies, buttery cookies

Find it online: https://cookedbycleo.com/pineapple-upside-down-sugar-cookies-recipe/