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Pineapple Upside-Down Cookies – A Fun Twist on a Classic Dessert Recipe

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  • Author: Maria
  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Total Time: 30 minutes
  • Yield: 24 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Description

Pineapple Upside-Down Cookies offer a delightful twist on the classic dessert with caramelized pineapple centers nestled in soft, buttery cookie dough. These 24 cookies combine warm cinnamon, tangy pineapple, and brown sugar in a simple baked treat that’s perfect for any occasion.


Ingredients

Scale

Cookie Dough

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 tsp vanilla extract
  • 2 ½ cups all-purpose flour
  • ½ tsp baking soda
  • ¼ tsp salt

Pineapple Topping

  • 1 cup canned pineapple, drained and chopped
  • ½ cup brown sugar, packed
  • 1 tsp ground cinnamon

Optional Garnish

  • Chopped walnuts or maraschino cherries for garnish

Additional Garnishes and Serving

  • 1 tablespoon olive oil
  • 1 tablespoon fresh lime juice
  • Fresh cilantro, chopped (for garnish)
  • Sliced lime wedges for serving


Instructions

  1. Preheat Oven: Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper or silicone baking mats to prevent sticking and ensure even baking.
  2. Cream Butter and Sugar: Beat the softened butter and granulated sugar together in a mixing bowl until the mixture is light, fluffy, and creamy, which should take about 2-3 minutes.
  3. Add Wet Ingredients: Mix in the egg and vanilla extract until the batter is smooth and well combined, ensuring an even distribution of flavors.
  4. Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually add this dry mixture to the butter mixture, stirring gently until just combined to avoid overmixing.
  5. Prepare Pineapple Mixture: In a small bowl, combine the drained chopped pineapple, brown sugar, and ground cinnamon. Set this mixture aside to allow the flavors to meld.
  6. Form Cookies and Add Topping: Scoop about 1 tablespoon of the dough and roll it into a ball. Place each ball onto the prepared baking sheet and press an indentation into the center of each cookie. Spoon a small amount of the pineapple mixture into each indentation carefully to avoid overflow.
  7. Bake: Bake the cookies in the preheated oven for 12-15 minutes, or until the cookies are golden around the edges and set. During baking, the pineapple topping will caramelize nicely.
  8. Cool Cookies: Let the cookies cool on the baking sheet for 5 minutes to firm up before transferring them to a wire rack to cool completely.

Notes

  • If desired, garnish cookies with chopped walnuts or maraschino cherries for added texture and visual appeal.
  • You may brush the cooled cookies with a mixture of olive oil and fresh lime juice for a subtle zest and shine.
  • Cookies can be stored in an airtight container at room temperature for up to 3 days.
  • For a gluten-free option, substitute the all-purpose flour with a gluten-free flour blend.
  • Ensure pineapple is well-drained to prevent excess moisture in the cookies.