The inspiration behind the pineapple upside down sugar cookies recipe stems from a personal preference for enjoying the toppings of desserts like pineapple upside down cake, only to be left with plain cake afterwards. This led to the creation of a cookie version where the topping-to-cookie ratio is more balanced, ensuring a satisfying treat from start to finish.
Ingredients
For the Cookies
- 1 cup butter (room temperature)
- 1 ½ cups granulated sugar
- 2 eggs
- 2 teaspoons vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- ½ teaspoon salt
For the Toppings
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup melted butter
- 1 cup packed light brown sugar
Instructions
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.
Mix Cookie Dough
- 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.