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Pineapple Upside-Down Cookies

A fun twist on a classic dessert, these cookies bring the nostalgic flavors of pineapple upside-down cake into a chewy, delightful cookie form.
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Prep Time 15 minutes
Cook Time 12 minutes
Total Time 27 minutes
Servings: 24 cookies
Course: Dessert, Snack
Cuisine: American, Tropical
Calories: 130
Ingredients Method Notes

Ingredients
  

Cookie Base
  • ½ cup Unsalted Butter, softened Use high-quality unsalted butter for best flavor.
  • ¾ cup Granulated Sugar Can substitute with brown sugar for richer flavor.
  • 1 Large Egg For egg-free version, use a flax egg.
  • 1 tsp Vanilla Extract Enhances sweetness.
  • 1 ¼ cups All-Purpose Flour Gluten-free flour blend can be used.
  • ½ tsp Baking Powder Provides subtle rise.
  • ¼ tsp Salt Balances sweetness.
Topping
  • ½ cup Brown Sugar Creates syrupy effect when baked.
  • 2 tbsp Melted Butter Helps mix brown sugar into syrup.
  • 1 small can Pineapple Rings, cut into smaller pieces Fresh pineapple can also be used.
  • ½ Maraschino Cherries, halved For color and sweetness.

Method
 

Prepare the Cookie Dough
  1. Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
  2. In a large bowl, cream together softened butter and granulated sugar until light and fluffy, about 3 minutes.
  3. Add the egg and vanilla extract, mixing until combined.
  4. In a separate bowl, whisk together flour, baking powder, and salt. Gradually combine with the butter-sugar blend.
Prepare the Topping
  1. In a small saucepan over low heat, combine melted butter and brown sugar until dissolved, creating a syrup.
Assemble the Cookies
  1. Spread a spoonful of the brown sugar mixture on the bottom of each cookie dough ball. Top with pineapple pieces and a half cherry.
Bake the Cookies
  1. Bake in the oven for 10-12 minutes until edges are golden and cookies are set in the center.
Serve and Enjoy
  1. Allow to cool for 5 minutes on the baking sheet before transferring to a wire rack to cool completely.

Notes

These cookies can be stored in an airtight container at room temperature for up to 3 days, or in the fridge for up to a week. You can also prepare the dough ahead of time and refrigerate it for up to 2 days before baking.