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Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies


  • Author: Jonathan
  • Total Time: 35 minutes
  • Yield: 24 cookies 1x
  • Diet: Gluten Free

Description

These Pineapple Upside Down Sugar Cookies offer a delightful tropical twist on a classic favorite, combining soft, buttery sugar cookies with caramelized pineapple topping for a perfect balance of sweet and tangy flavors. Ideal for any occasion, these cookies feature a melt-in-your-mouth texture and a beautifully sticky, flavorful pineapple caramel topping that brings a mini celebration to every bite.


Ingredients

Scale

For the Pineapple Topping

  • 1 cup fresh pineapple chunks
  • 1/3 cup brown sugar (natural)
  • 1 tsp natural gelling agent

For the Sugar Cookie Dough

  • 2 1/4 cups all-purpose flour (or gluten-free baking blend)
  • 3/4 cup granulated sugar
  • 3/4 cup unsalted butter (plant-based), softened
  • 1 tsp baking powder
  • 1 tbsp apple cider vinegar (natural)
  • 1 tsp vanilla extract (natural)
  • 2 tsp cornstarch (natural)

Instructions

  1. Prepare the Pineapple Topping: Mix the fresh pineapple chunks with the brown sugar (natural) and natural gelling agent. Gently cook the mixture over low heat until it becomes sticky and caramel-like, creating a flavorful topping that mimics the classic upside-down cake effect.
  2. Create the Sugar Cookie Dough: In a large bowl, cream together the softened unsalted butter (plant-based) and granulated sugar until light and fluffy. Add apple cider vinegar (natural) and vanilla extract (natural), then gradually mix in the all-purpose flour (or gluten-free blend), cornstarch (natural), and baking powder until just combined to maintain tenderness.
  3. Assemble the Cookies: Preheat the oven to 350°F (175°C) and line cookie sheets with parchment paper. Scoop the dough into small, even rounds, flatten each gently, and press a spoonful of the pineapple topping firmly into the center of each cookie, allowing the caramelized mixture to integrate slightly with the dough.
  4. Bake and Cool: Bake the cookies until the edges turn golden and the pineapple topping bubbles lightly, approximately 12-15 minutes. Allow the cookies to cool fully on the baking sheet so the topping can set before transferring to a wire rack.

Notes

  • Use fresh pineapple for optimal flavor and texture in the topping.
  • Mix the dough just until combined to ensure tender and soft cookies.
  • Adjust the amount of brown sugar (natural) in the topping to control caramelization and sweetness.
  • If the dough feels too soft, chill for 30 minutes before baking to maintain shape.
  • Line baking sheets with parchment paper to prevent sticking and ease cleanup.
  • Prep Time: 20 minutes
  • Cook Time: 15 minutes
  • Category: Appetizers
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 150
  • Sugar: 12g
  • Sodium: 80mg
  • Fat: 7g
  • Saturated Fat: 2g
  • Unsaturated Fat: 5g
  • Trans Fat: 0g
  • Carbohydrates: 20g
  • Fiber: 1g
  • Protein: 1g
  • Cholesterol: 0mg

Keywords: Pineapple Upside Down Sugar Cookies, tropical sugar cookies, pineapple cookies, vegan cookies, gluten-free cookies, caramelized pineapple cookies