Description

Delight in these Pineapple Upside-Down Cookies, a charming twist on the classic dessert. Featuring a caramelized topping of buttery brown sugar, juicy pineapple rings, and maraschino cherries baked beneath a soft, flavorful cookie dough, these treats combine tropical sweetness with a tender cookie texture. Perfect for gatherings or a special sweet snack, these cookies boast a beautiful presentation when inverted after baking.

Ingredients

Topping Layer:

1/2 cup unsalted butter, melted
1/2 cup light brown sugar
6 canned pineapple rings (halved or trimmed to fit molds)
6 maraschino cherries

Cookie Dough:

1 cup unsalted butter, room temperature
1 cup granulated sugar
1/2 cup packed light brown sugar
2 large eggs
1 tsp vanilla extract
1/2 cup sour cream
3 cups all-purpose flour
1 tsp baking powder
1/2 tsp baking soda
1/4 tsp salt
2 tsp cornstarch

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Instructions

Preheat and Prepare Pan: Preheat your oven to 350°F (175°C). Lightly grease or spray a muffin pan to prevent sticking and allow easy removal of the cookies after baking.
Assemble Topping: Pour 1 teaspoon of melted butter and 1 teaspoon of brown sugar into each muffin cup. Place a halved pineapple ring and one maraschino cherry in the center of each cup, creating the caramelized and fruity topping layer.
Make Cookie Dough: In a large bowl, beat the room temperature butter together with granulated sugar and brown sugar until the mixture becomes light and fluffy. Add eggs one at a time, mixing well after each addition, then stir in the vanilla extract and sour cream for moisture and richness.
Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, salt, and cornstarch to evenly distribute the leavening agents and thickeners.
Mix Dough: Gradually add the dry ingredients into the wet mixture, stirring just until combined to form a soft dough with a tender crumb.
Fill Muffin Cups: Spoon or scoop the cookie dough over the pineapple and cherry in each cup, filling almost to the top to cover the fruit completely and bake evenly.
Bake Cookies: Bake in the preheated oven for 18 to 22 minutes, or until the cookies are golden brown and set in the center.
Cool and Invert: Allow the cookies to cool in the pan for about 10 minutes. Then, carefully invert each cookie onto a wire rack so the caramelized pineapple and cherry topping is displayed beautifully on top.

Notes

For best results, use canned pineapple rings that are well-drained to prevent excess moisture in the cookies.
Make sure the butter is at room temperature for the cookie dough to achieve a fluffy texture.
You can customize with other fruits like peach slices or use different flavored cherries for variation.
Cool cookies slightly before inverting to avoid breaking or sticking.
Store cookies in an airtight container at room temperature for up to 3 days.