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  • Author: asma
  • Total Time: 30 minutes
  • Yield: 13 cookies 1x
  • Diet: Vegetarian

Description

These Pineapple Upside-Down Cookies bring all the flavors of the classic cake into a bite-sized treat! Featuring a buttery vanilla cookie base, tangy pineapple slices, and a caramelized topping, these cookies are soft, chewy, and bursting with tropical flavor—perfect for any occasion!


Ingredients

Scale

For the Cookie Dough:

  • 1 cup butter, room temperature
  • 1 1/2 cups granulated sugar
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 1/2 cup sour cream
  • 3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon cornstarch
  • 1/2 teaspoon salt

For the Pineapple Topping:

  • 13 canned pineapple slices, drained and patted dry
  • 1/2 cup brown sugar (optional, for caramelization)

Instructions

Step 1: Preheat & Prep

  1. Preheat oven to 350°F (175°C).
  2. Line a baking sheet with parchment paper.

Step 2: Make the Cookie Dough

  1. In a large mixing bowl, beat butter and sugar until light and fluffy.
  2. Add eggs, vanilla extract, and sour cream, mixing until well combined.
  3. In a separate bowl, whisk together flour, baking powder, cornstarch, and salt.
  4. Gradually add dry ingredients to the wet mixture, mixing until a soft dough forms.

Step 3: Assemble the Cookies

  1. Scoop tablespoon-sized portions of dough onto the baking sheet, spacing them 2 inches apart.
  2. Press a pineapple slice gently into the center of each cookie.
  3. Sprinkle brown sugar over the pineapple slices for a caramelized finish (optional).

Step 4: Bake & Cool

  1. Bake for 12-15 minutes, or until cookies are set and lightly golden around the edges.
  2. Let cool for 5 minutes on the baking sheet before transferring to a wire rack.

Serving & Storage:

  • Serve warm or at room temperature for the best flavor.
  • Store in an airtight container at room temperature for up to 3 days or refrigerate for up to 5 days.

Notes

  • For extra caramelization, brush pineapple slices with melted butter and brown sugar before baking.
  • Make them extra tropical by adding ¼ cup shredded coconut to the cookie dough!
  • Want a cherry on top? Place a maraschino cherry in the center of each pineapple slice before baking.
  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Category: Desserts
  • Method: Baking
  • Cuisine: American