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Pineapple Upside Down Sugar Cookies Recipe

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★★★★★

4.6 from 132 reviews

These Pineapple Upside Down Sugar Cookies combine the sweet, caramelized flavor of classic pineapple upside-down cake with the soft, buttery texture of sugar cookies. Each cookie features a juicy pineapple ring topped with a maraschino cherry and a golden brown cookie baked right on top, creating a visually stunning and delicious treat perfect for any occasion.

Ingredients

Scale

Cookie Dough

  • 1 1/2 cups all-purpose flour
  • 3/4 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 1 egg
  • 1 1/2 tsp baking powder
  • 1/4 tsp salt

Toppings

  • 6 canned pineapple rings
  • 1/2 cup brown sugar
  • 12 maraschino cherries (for garnish)

Instructions

  1. Preheat Oven and Prepare Baking Sheet: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking and ensure easy cleanup.
  2. Cream Butter and Sugar: In a mixing bowl, beat together the softened butter and granulated sugar until the mixture becomes light and fluffy, which ensures a tender cookie texture.
  3. Add Egg: Incorporate the egg into the creamed mixture and mix thoroughly to combine all wet ingredients smoothly.
  4. Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, and salt to evenly distribute the leavening agent and seasoning.
  5. Combine Dry and Wet Ingredients: Gradually add the dry mixture to the wet ingredients, stirring until just combined to avoid overmixing that can toughen the cookies.
  6. Prepare Pineapple Toppings: Place a small spoonful of brown sugar in the center of each pineapple ring on the prepared baking sheet; this will caramelize during baking for that signature upside-down flavor.
  7. Add Cherries: Position a maraschino cherry in the center of each pineapple ring atop the brown sugar, adding a classic garnish and a pop of color.
  8. Shape and Place Dough: Scoop tablespoon-sized portions of cookie dough and slightly flatten them before placing each gently on top of a pineapple ring with cherry.
  9. Bake Cookies: Bake all the assembled cookies in the preheated oven for 10-12 minutes until the cookies turn lightly golden brown and are cooked through.
  10. Cool Cookies: Let the cookies cool on the baking sheet for several minutes to allow them to set, then transfer them to a wire rack to cool completely without becoming soggy.
  11. Serve: Enjoy these Pineapple Upside Down Sugar Cookies warm or at room temperature as a delightful treat that blends fruit and sweetness perfectly.

Notes

  • For best results, use fresh canned pineapple rings drained well to avoid excess moisture making the cookie soggy.
  • Chilling the cookie dough for 15-20 minutes before scooping can make it easier to handle.
  • Store cookies in an airtight container at room temperature for up to 3 days to maintain freshness.
  • You can substitute light brown sugar for a more subtle caramel flavor or dark brown sugar for a richer, deeper taste.
  • These cookies make a festive addition to holiday cookie trays or summer parties.

Keywords: pineapple upside down cookies, sugar cookies, pineapple cookies, cherry topped cookies, baked fruit cookies, easy dessert recipes

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