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Pineapple Upside-Down Sugar Cookies

These delightful Pineapple Upside-Down Sugar Cookies blend chewy and crispy textures, topped with sweet caramelized pineapple for a tropical treat.
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Prep Time 15 minutes
Cook Time 18 minutes
Total Time 33 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 120
Ingredients Method Notes

Ingredients
  

Cookie Base
  • 1 cup unsalted butter, softened Provides necessary richness.
  • 1 cup granulated sugar Balances the tangy notes of the pineapple.
  • 1 large egg Binding agent for tender texture.
  • 1 tsp vanilla extract Enhances flavor profile.
  • 2.5 cups all-purpose flour Gives structure to cookies.
  • 1 tsp baking soda Leavening agent for rising.
  • 0.5 tsp baking powder Enhances fluffiness.
  • 0.25 tsp salt Balances sweetness.
Topping
  • 0.5 cup brown sugar, packed Adds depth and moisture.
  • 0.25 cup unsalted butter, melted Deepens flavor and aids caramelization.
  • 1 can (20 oz) sliced pineapple, drained The star of the cookie.
  • to taste pieces Maraschino cherries (optional) Adds color and sweetness.

Method
 

Preparation
  1. Preheat your oven to 350°F (175°C) and prepare a muffin tin by lining it with cupcake liners or greasing it lightly.
  2. In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Then, beat in the egg and vanilla extract until smooth.
  3. In another bowl, whisk together the flour, baking soda, baking powder, and salt. Gradually fold the dry ingredients into the wet mixture until just combined.
  4. In a small bowl, mix the brown sugar and melted butter to form a glaze. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup.
  5. Place a slice of pineapple on top of the brown sugar mixture in each muffin cup, optionally adding a maraschino cherry in the center.
Baking
  1. Drop about 1 tablespoon of cookie dough on top of each pineapple slice, spreading it slightly to cover.
  2. Bake for 15-18 minutes or until the cookie tops are lightly golden and set.
  3. Let the cookies cool in the pan for about 5 minutes before transferring them to a wire rack to cool completely.
Serving
  1. Enjoy your cookies warm or at room temperature, with options to pair them with a glass of cold milk or tea.

Notes

Ensure butter is at room temperature for best texture. Use fresh pineapple for an added freshness.