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Pineapple Upside-Down Sugar Cookies

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  • Prep Time: 15 minutes
  • Cook Time: 20 minutes
  • Total Time: 35 minutes
  • Yield: 12 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

Buttery sugar cookies baked in muffin tins with a caramelized brown sugar pineapple topping and a cherry center, delivering all the nostalgia of pineapple upside-down cake in petite, glossy bites.


Ingredients

Scale
  • 1/2 cup unsalted butter, melted
  • 1/2 cup packed brown sugar
  • 6 to 8 canned pineapple rings, patted dry
  • 6 to 8 maraschino cherries, drained and patted dry
  • 1 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon fine salt


Instructions

  1. Preheat oven to 350°F (175°C). Lightly grease a standard 12-cup muffin tin.
  2. Stir the melted butter and brown sugar together. Spoon about 1 tablespoon into the bottom of each muffin cup.
  3. Place a pineapple ring in each cup, trimming or halving rings to fit as needed. Nestle a cherry in the center.
  4. Cream the softened butter and granulated sugar until light. Beat in the egg and vanilla until smooth.
  5. Whisk flour, baking powder, and salt, then mix into the wet ingredients until a soft dough forms.
  6. Portion dough with a scoop and gently press on top of the pineapple in each cup. Bake 18 to 22 minutes until golden at the edges.
  7. Cool 5 minutes, then invert the pan onto a rack. Let set and serve warm or at room temperature.

Notes

  • Pat pineapple and cherries very dry to prevent soggy tops.
  • Use room temperature ingredients for a smooth, even dough.
  • A pinch of cinnamon in the brown sugar adds cozy warmth.
  • Drizzle a light vanilla glaze after cooling for extra shine.
  • For gluten free, use a 1:1 baking blend and monitor bake time.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 210
  • Sugar: 18 g
  • Sodium: 95 mg
  • Fat: 9 g
  • Saturated Fat: 5 g
  • Unsaturated Fat: 3 g
  • Trans Fat: 0 g
  • Carbohydrates: 30 g
  • Fiber: 1 g
  • Protein: 2 g
  • Cholesterol: 30 mg