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Pineapple upside down sugar cookie with caramelized topping

Pineapple Upside Down Sugar Cookies

  • Author: Savannah
  • Total Time: ~45 minutes
  • Yield: 12–16 cookies 1x
  • Diet: Vegetarian

Description

Soft, buttery sugar cookies topped with caramelized pineapple and a cherry, inspired by the classic pineapple upside down cake. These cookies are easy to make, perfect for parties, and bring a nostalgic old fashioned flavor to every bite.

Ingredients

Scale

🛒 Ingredients (for 12–16 cookies):

For the Cookie Dough:

  • 2 ½ cups all-purpose flour

  • 1 teaspoon baking powder

  • ½ teaspoon baking soda

  • ¼ teaspoon salt

  • ½ cup (1 stick) unsalted butter, softened

  • ½ cup vegetable oil

  • 1 cup granulated sugar

  • 1 large egg

  • 1 teaspoon vanilla extract

For the Pineapple Topping:

  • ½ cup brown sugar, packed

  • 2 tablespoons unsalted butter, melted

  • 8–10 small pineapple rings or chopped pineapple chunks

  • 12 maraschino cherries (optional, for garnish)

Instructions

📝 Instructions:

Step 1: Prep Pineapple Topping

  1. Preheat oven to 350°F (175°C).

  2. Mix brown sugar and melted butter in a small bowl.

  3. Line a baking sheet with parchment paper. Spoon a teaspoon of the brown sugar mixture onto each cookie space. Top each with a small pineapple piece and optionally a cherry.

Step 2: Make Cookie Dough

  1. In a medium bowl, whisk flour, baking powder, baking soda, and salt.

  2. In a large bowl, cream butter, oil, and sugar until smooth. Beat in egg and vanilla.

  3. Gradually add dry ingredients, mixing until dough forms.

Step 3: Assemble Cookies

  1. Scoop dough (about 1 tablespoon each) and gently press on top of the pineapple topping.

  2. Slightly flatten each cookie with your hand or a spoon.

Step 4: Bake

  1. Bake for 12–15 minutes, or until edges are lightly golden.

  2. Remove from oven and let cool on the pan for 5 minutes, then carefully transfer to a wire rack.

Step 5: Serve & Enjoy

  1. Serve warm or at room temperature. Cookies can be stored in an airtight container for up to 4 days.

Notes

  • Chewy or Soft: Slightly underbake for softer cookies.

  • Mini Version: Use smaller dough portions for bite-sized treats.

  • Make Ahead: Dough can be refrigerated for 24 hours before baking.

  • Prep Time: 20 minutes
  • Cook Time: 12–15 minutes
  • Category: Dessert / Cookie
  • Method: Baked / Topped / Decorated
  • Cuisine: American

Find it online: https://www.eminentrecipes.com/pineapple-upside-down-sugar-cookies/