Preheat Oven and Prepare Pan

    • Preheat the oven to 350 degrees Fahrenheit.

 

  • Set aside a USA Pan mini round cake pan or a similar baking pan.
    • In a large mixing bowl, combine the butter and sugar until light and fluffy.
    • Add the eggs, vanilla extract, and sour cream; mix until combined.
    • Add the flour, baking powder, cornstarch, and salt; mix until the dough just comes together. Set aside.

Prepare Brown Sugar Glaze

  • In a separate bowl, stir together the melted butter and brown sugar until combined.

Assemble Cookies

    • Add about a tablespoon of the brown sugar mixture to the bottom of each cavity in the pan. Spread it around to cover the bottom.
    • Place a pineapple slice on top of the brown sugar and a maraschino cherry in the center of the pineapple.
  • Add a 3-tablespoon cookie scoop of cookie dough to the top and flatten it using an offset spatula.

Bake and Cool

    • Bake for 25 minutes or until the edges are golden brown and the brown sugar is bubbling up the sides.
    • Let cool for 10 minutes, then turn out onto a wax paper-covered surface. If the pineapple sticks to the pan, reposition it back on the cookie.
    • Let cool completely before eating.

Storage and Best Consumption

  • These cookies are best consumed within the first 2-3 days.
  • Store them in an airtight container.

Additional Tips and Recommendations

  • The use of a USA Pan mini round cake pan is recommended, as it can be used for multiple recipes.
  • Other great pineapple desserts mentioned include Pineapple Upside Down Skillet Cake, Pineapple Carrot Cake with Cream Cheese Frosting, and No-Bake Pineapple Cream Dessert.

Tips for Making the Best Pineapple Upside Down Sugar Cookies

    • Ensure the butter is at room temperature for easier mixing.
  • Use wax paper to prevent the brown sugar from sticking and making a mess.
  • If the pineapple sticks to the pan, gently reposition it back on the cookie after cooling.

Delicious Twist on Tradition

Pineapple upside down sugar cookies are a creative and delicious twist on traditional desserts. With their balanced topping-to-cookie ratio and the ease of using canned ingredients, these cookies are a perfect treat for any occasion, offering a sweet and satisfying experience with each bite. They are ideal for summer but can be enjoyed year-round due to the availability of canned pineapple and maraschino cherries.

Summary

Pineapple Upside Down Delight Cookies are delicious treats that combine the nostalgic tastes of pineapple upside-down cake with the convenience and texture of cookies, perfect for any dessert lover.