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Pineapple Upside Down Sugar Cookies

These delightful cookies capture the flavors of traditional pineapple upside-down cake in a fun, bite-sized treat, topped with caramelized pineapple and cherries.
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Prep Time 20 minutes
Cook Time 15 minutes
Total Time 35 minutes
Servings: 24 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 150
Ingredients Method Notes

Ingredients
  

Cookie Base Ingredients
  • 1 cup unsalted butter, softened Ensure the butter is properly softened, yielding to gentle pressure.
  • 1 cup granulated sugar
  • 1 egg
  • 1 teaspoon vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
Topping
  • 1/2 cup crushed pineapple, drained Ensure the pineapple is well-drained to prevent soggy cookies.
  • as needed Maraschino cherries, halved Use as a topping for each cookie.

Method
 

Preparation
  1. Preheat your oven to 350°F (175°C) and line your baking sheets with parchment paper.
  2. Soften the butter so it yields to gentle pressure but still holds its shape.
  3. Drain the crushed pineapple thoroughly, pressing out excess moisture with a paper towel.
Create the Cookie Base
  1. In a large bowl, cream together the softened butter and granulated sugar until light and fluffy, about 3-4 minutes with an electric mixer.
  2. Add the egg and vanilla extract, beating until fully incorporated.
Add Dry Ingredients
  1. In a separate bowl, whisk together the all-purpose flour, baking powder, and salt until evenly combined.
  2. Gradually add the dry mixture to the wet ingredients, mixing on low speed just until incorporated.
  3. Stop mixing as soon as no dry streaks remain to prevent tough cookies.
Incorporate the Pineapple
  1. Gently fold in the well-drained crushed pineapple using a spatula until evenly distributed.
Form and Bake the Cookies
  1. Using a cookie scoop or tablespoon, drop rounded portions of dough onto prepared baking sheets, spacing them about 2 inches apart.
  2. Press a halved maraschino cherry into the center of each cookie, gently pushing it down.
  3. Bake for 12-15 minutes until the edges are lightly golden but the centers still look slightly soft.

Notes

Store cookies in an airtight container at room temperature for up to one week. If freezing, use a resealable bag for up to three months.