Try these Pineapple Upside-Down Sugar Cookies for a unique take on a classic dessert. Start by preheating your oven to 350°F and preparing your mini round cake pan. In a large bowl, cream together butter and granulated sugar. Add eggs, vanilla extract, and sour cream, mixing until combined. Then incorporate the dry ingredients: flour, baking powder, cornstarch, and salt. Separately, mix melted butter with brown sugar. Place a spoonful of this mixture in each pan cavity, top with a pineapple slice and maraschino cherry, and cover each with a scoop of cookie dough. Bake for 25 minutes or until golden brown. Cool for 10 minutes before turning out onto a wax paper-lined surface. Let the cookies cool completely before serving. Store in an airtight container for up to 7 days.

Pineapple Upside-Down Cookie Delights
Pineapple upside-down cookie delights | Myhomemaderecipe.com

Pineapple Upside Down Sugar Cookies are the perfect summer treat, combining the delightful flavors of a classic pineapple upside down cake with the convenience and portion control of cookies. This recipe was inspired by my own love for the toppings of desserts like pineapple upside down cake. Often, I find myself enjoying the caramelized pineapple and cherries more than the cake itself. This led me to create a cookie version that captures the essence of these toppings while providing a soft, fluffy sugar cookie base.

Recipe Overview

This Pineapple Upside Down Sugar Cookie recipe is quick, easy, and perfect for any time of the year. Here’s a brief overview of what you can expect:

  • Prep Time: 20 minutes
  • Cook Time: 25 minutes
  • Total Time: 45 minutes

The use of canned pineapple slices and maraschino cherries makes this recipe accessible year-round, eliminating the need for fresh ingredients that may be seasonal.

Ingredients

To make these delicious Pineapple Upside Down Sugar Cookies, you will need the following ingredients:

  • 1 cup butter (room temperature)
  • 1 ½ cups granulated sugar
  • 2 eggs
  • 2 tsp. vanilla extract
  • ½ cup sour cream
  • 3 cups all-purpose flour
  • 1 tsp. baking powder
  • 1 tsp. cornstarch
  • ½ tsp. salt
  • 13 canned pineapple slices
  • 13 maraschino cherries
  • ½ cup melted butter
  • 1 cup light brown sugar (packed)

These ingredients will help you create a cookie that is both flavorful and visually appealing.

Instructions

Preheat Oven and Prepare Pan

To start, preheat your oven to 350 degrees Fahrenheit. For this recipe, it is highly recommended to use a USA Pan mini round cake pan or a similar mini cake pan. These pans are ideal for creating individual cookies with a perfectly portioned topping.

In a large mixing bowl, combine the butter and sugar. Mix until the mixture becomes light and fluffy, which should take about 2-3 minutes. Add the eggs, vanilla extract, and sour cream, and continue mixing until all the ingredients are well combined.

Next, add the flour, baking powder, cornstarch, and salt. Mix until the dough just comes together. It is important not to overmix at this stage, as it can make the cookies dense. Set the dough aside for later use.

Prepare Brown Sugar Mixture

In a separate bowl, mix together the melted butter and light brown sugar until they are well combined. This mixture will serve as the glaze for the bottom of each cookie, adding a rich, caramelized flavor.

Assemble Cookies

Lightly spray the mini round cake pan with non-stick spray to ensure the cookies will release easily. Add about a tablespoon of the brown sugar mixture to the bottom of each cavity in the pan. Spread it slightly to cover the bottom.

Place a pineapple slice on top of the brown sugar and a maraschino cherry in the center of the pineapple. This will create the signature upside-down effect of the cookies.

Scoop about 3 tablespoons of the cookie dough into each cavity, using an offset spatula or the back of a spoon to flatten and spread the dough evenly. This ensures that the cookie will bake uniformly and hold its shape.

Bake

Bake the cookies for 25 minutes or until the edges are golden brown and the brown sugar is bubbling up the sides. This bubbling is a sign that the cookies are done and the glaze is caramelized.

Cool and Serve

Let the cookies cool for 10 minutes in the pan before turning them out onto a wax paper covered surface. If any pineapple slices stick to the pan, simply reposition them back onto the cookie. Let the cookies cool completely before serving.

Store the cookies in an airtight container. They are best if eaten within the first 2-3 days, as the freshness of the ingredients and the texture of the cookies are optimal during this period.

Additional Notes

Versatility of the USA Pan Mini Round Cake Pan

The USA Pan mini round cake pan is a versatile tool in your baking arsenal. Besides making these Pineapple Upside Down Sugar Cookies, you can use it for various other recipes such as mini cakes, muffins, and even savory dishes. The non-stick coating and durable construction make it a valuable investment for any home baker.

Other Great Pineapple Desserts

If you enjoy the flavors of pineapple and are looking for other delicious desserts, here are a few suggestions:

  • Pineapple Upside Down Skillet Cake: A large, skillet-baked version of the classic pineapple upside down cake, perfect for family gatherings or potlucks.
  • Pineapple Carrot Cake with Cream Cheese Frosting: A moist carrot cake infused with the sweetness of pineapple and topped with a tangy cream cheese frosting.
  • No-Bake Pineapple Cream Dessert: A light and refreshing dessert made with pineapple, cream, and a graham cracker crust, perfect for hot summer days.

These desserts offer different ways to enjoy the tropical flavor of pineapple and can be great additions to your dessert repertoire.

Tips and Variations

Tips for Making the Cookies

To ensure your cookies turn out perfectly, here are a few tips:

  • Use a Cookie Sheet Under the Pan: To catch any brown sugar that bubbles over during baking, place a cookie sheet under the mini cake pan. This will make cleanup easier and prevent any mess.
  • Fresh vs. Canned Ingredients: While canned pineapple slices and maraschino cherries are convenient and accessible year-round, you can also use fresh ingredients if they are available. Fresh pineapple slices will add a slightly different texture and flavor, but they work beautifully in this recipe.
  • Adjusting the Brown Sugar Mixture: If you find that the brown sugar mixture is too thick, you can add a little more melted butter to achieve the desired consistency.

Variations

Here are some variations you can try to make the recipe more interesting:

  • Different Types of Cherries: Instead of using maraschino cherries, you can experiment with other types of cherries like fresh cherries or even cranberries for a different flavor profile.
  • Adding Spices: A pinch of cinnamon or nutmeg can add a warm and comforting flavor to the cookies, especially during the fall and winter seasons.
  • Using Different Pans: While the mini round cake pan is ideal, you can also use muffin tins or even a regular cookie sheet if you don’t have the mini pans. Adjust the baking time accordingly based on the size of the cookies.

Conclusion

Pineapple Upside Down Sugar Cookies are a delightful summer treat that combines the best of both worlds: the caramelized sweetness of pineapple upside down cake and the convenience of individual cookies. With their soft, fluffy sugar cookie base, caramelized brown sugar glaze, and sweet pineapple and cherry toppings, these cookies are sure to be a hit at any gathering.

The recipe is easy to follow, and the use of canned ingredients makes it accessible year-round. Whether you are a seasoned baker or just starting out, this recipe is a great addition to your baking repertoire.

Encourage your readers to try this recipe and share their experiences. The feedback and variations shared by readers can often lead to new ideas and improvements, making the recipe even more enjoyable for everyone.

Final Thoughts

Baking is not just about following a recipe; it's about creating something special that brings joy to those who taste it. These Pineapple Upside Down Sugar Cookies are more than just a dessert; they are a way to share love and happiness with family and friends. So go ahead, bake a batch, and enjoy the sweet and tangy flavors of summer in every bite.