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Pineapple Upside-Down Sugar Cookies

Delightful cookies combining the flavors of pineapple upside-down cake with the charm of sugar cookies, perfect for any occasion.
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Prep Time 20 minutes
Cook Time 18 minutes
Total Time 38 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American, Tropical
Calories: 180
Ingredients Method Notes

Ingredients
  

Cookie Base
  • 1 cup unsalted butter, softened This creamy fat produces a tender cookie base.
  • 1 cup granulated sugar Imparts the right amount of sweetness.
  • 1 large egg Gives the cookies structure and moistness.
  • 1 tsp vanilla extract Enhances the overall flavor.
  • 2 1/2 cups all-purpose flour Gives the cookie a perfect chewy texture.
  • 1 tsp baking soda Contributes lift and spread.
  • 1/2 tsp baking powder Works with baking soda for ideal height.
  • 1/4 tsp salt Balances sweetness and enhances flavors.
Pineapple Topping
  • 1/2 cup brown sugar, packed Adds depth to the topping.
  • 1/4 cup unsalted butter, melted Creates a gooey base for the pineapple.
  • 1 can (20 oz) sliced pineapple, drained Provides the tropical kick.
  • to taste Maraschino cherries (optional) Adds sweetness and color.

Method
 

Preparation
  1. Preheat your oven to 350°F (175°C).
  2. Prepare your muffin tin by lining it with cupcake liners or lightly greasing it.
  3. In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
  4. Add the egg and vanilla extract, beating until well combined.
  5. In another bowl, whisk together the all-purpose flour, baking soda, baking powder, and salt.
  6. Gradually add the dry mixture to your wet ingredients, mixing just until combined.
Assembly
  1. In a small bowl, mix together the brown sugar and melted butter until well combined.
  2. Spoon about 1 teaspoon of the brown sugar mixture into the bottom of each muffin cup.
  3. Place a slice of pineapple on top of the brown sugar mixture in each muffin cup.
  4. Drop about 1 tablespoon of cookie dough on top of each pineapple slice, spreading it slightly to cover the fruit.
Baking
  1. Bake in the preheated oven for 15-18 minutes until the tops are lightly golden.
  2. Cool the cookies for about 5 minutes in the pan before transferring them to a wire rack to cool completely.
Serving
  1. Enjoy your Pineapple Upside-Down Sugar Cookies warm or at room temperature.

Notes

For a healthier option, substitute half of the butter with Greek yogurt or applesauce. Keep cookies in an airtight container for up to five days. These cookies freeze well; layer them between parchment paper and store for up to three months.