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Pineapple Upside Down Cookies with colorful cherry and pineapple topping

Pineapple Upside Down Sugar Cookies

Delightful cookies that combine the classic flavors of pineapple upside-down cake with a soft and chewy sugar cookie base, perfect for any occasion.
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Prep Time 10 minutes
Cook Time 20 minutes
Total Time 30 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 130
Ingredients Method Notes

Ingredients
  

Cookie Base
  • 2 cups all-purpose flour Can substitute with gluten-free flour blend.
  • 1 cup granulated sugar For the cookie base.
  • 1/2 cup butter, softened Use room temperature butter for best texture.
  • 1 large egg At room temperature.
  • 1 teaspoon vanilla extract
  • 2 teaspoons baking powder Ensure gluten-free if needed.
Pineapple Topping
  • 1 can pineapple rings Canned or thinly sliced fresh pineapple can be used.
  • 12 pieces maraschino cherries One for each pineapple ring.

Method
 

Preparation
  1. Gather your ingredients: flour, sugar, butter, eggs, baking powder, vanilla extract, a can of pineapple rings, and maraschino cherries.
  2. Preheat your oven to 350°F (175°C).
  3. In a bowl, cream together the softened butter and sugar until light and fluffy.
  4. Add in the egg and vanilla, mixing well.
  5. In a separate bowl, combine flour and baking powder, then gradually add to the wet ingredients until fully combined.
Assembling and Baking
  1. In a baking dish, place the pineapple rings and cherries in the center of each ring.
  2. Using a scoop or spoon, place dollops of cookie dough over the pineapple and cherries, carefully spreading it to cover them.
  3. Bake for 15-20 minutes or until the edges are lightly golden.
  4. Allow the cookies to cool slightly before flipping them over to reveal the beautiful pineapple topping.

Notes

These cookies can be served on their own or with a scoop of vanilla ice cream or chocolate sauce. Store cookies in an airtight container at room temperature for up to a week or freeze for longer storage.