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Pineapple Upside Down Sugar Cookies — Soft, Caramel-Topped Holiday Cookies Pinterest recipe pin

Pineapple Upside Down Sugar Cookies

Soft sugar cookies topped with caramelized pineapple rings and an optional cherry, using a chilled-dough method to keep the topping glossy without soggy bottoms.
Print Recipe Pin Recipe
Prep Time 25 minutes
Cook Time 13 minutes
Total Time 48 minutes
Servings: 18 –20 cookies
Calories: 150
Ingredients Equipment Method Notes

Ingredients
  

  • 1 3/4 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon fine salt
  • 1/2 cup 1 stick unsalted butter, softened
  • 1/2 cup granulated sugar
  • 2 tablespoons packed light brown sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 can 8 ounces pineapple rings, drained and patted dry or 1 cup fresh pineapple rings, patted dry
  • 1/3 cup packed light brown sugar for glaze
  • 2 tablespoons unsalted butter for glaze
  • 1 teaspoon fresh lemon juice for glaze
  • Optional: 18 maraschino cherries drained

Equipment

  • 1 Rimmed baking sheet (half-sheet, 18 x 13 inches)
  • 1 Small nonstick skillet or 8-inch saucepan
  • 1 2-inch round cutter (optional)
  • 1 Parchment paper

Method
 

Prepare the topping
  1. In a small skillet over medium heat, combine 1/3 cup packed light brown sugar and 2 tablespoons butter; stir until sugar dissolves and mixture bubbles gently, 2–3 minutes.
  2. Stir in 1 teaspoon lemon juice, remove from heat, and spoon about 1 teaspoon of the warm glaze onto each pineapple ring placed on parchment; add a cherry in the center if using and let cool 10 minutes until tacky.
Make the dough
  1. Whisk 1 3/4 cups flour, 1 teaspoon baking powder, and 1/4 teaspoon salt in a bowl.
  2. Cream 1/2 cup softened butter with 1/2 cup granulated sugar and 2 tablespoons packed brown sugar until light, 2–3 minutes. Beat in 1 egg and 1 teaspoon vanilla until combined.
  3. Fold the dry ingredients into the wet just until combined, then cover and chill the dough 20 minutes.
Assemble and bake
  1. Preheat oven to 350°F and line baking sheets with parchment. Shape chilled dough into 18–20 balls, flatten to 1/2-inch discs, and place on prepared sheets.
  2. Top each disc with a glazed pineapple ring, pressing gently so cookie edges rise slightly around the ring. Chill assembled sheets 15–20 minutes.
  3. Bake at 350°F for 11–13 minutes until edges are set and lightly golden. Let cool on the sheet 3–4 minutes, then transfer to a rack to cool completely.

Notes

Drain and pat pineapple dry before glazing to avoid excess moisture. Chill assembled cookies before baking to prevent topping slippage and reduce spread. Cookies keep well in an airtight container at room temperature for up to 3 days; freeze plain baked cookies (without topping) for up to 2 months.