Description

Delight in these Pineapple Upside Down Sugar Cookies, a charming twist on the classic pineapple upside-down cake. Each mini cookie features a caramelized base of buttery brown sugar topped with a juicy pineapple slice and maraschino cherry, crowned with tender, vanilla-scented sugar cookie dough baked to golden perfection. Perfect for gatherings or a sweet treat, these cookies combine fruity freshness with rich, buttery sweetness in every bite.

Ingredients

Scale

Cookie Dough

1 cup butter (room temperature)
1 1/2 cups granulated sugar
2 eggs
2 tsp vanilla extract
1/2 cup sour cream
3 cups all-purpose flour
1 tsp baking powder
1 tsp cornstarch
1/2 tsp salt

Toppings

13 canned pineapple slices
13 maraschino cherries

Caramel Base

1/2 cup butter (melted)
1 cup light brown sugar (packed)

Instructions

Preheat Oven: Preheat your oven to 350°F (175°C). Prepare a USA pan mini round cake pan by setting it aside for assembly.
Make Cookie Dough: In a large mixing bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Add the eggs, vanilla extract, and sour cream, mixing until fully combined.
Add Dry Ingredients: Gradually incorporate the flour, baking powder, cornstarch, and salt into the wet mixture. Mix until the cookie dough just forms, then set aside.
Prepare Caramel Base: In a separate bowl, stir together melted butter and packed light brown sugar until smooth and combined.
Fill Pan with Caramel: Spoon about a tablespoon of the brown sugar mixture into the bottom of each cavity in the cake pan. Spread evenly to cover the base.
Add Fruit Toppings: Place a pineapple slice on top of the brown sugar in each cavity, then place a maraschino cherry in the center of each pineapple slice.
Top with Cookie Dough: Using a 3-tablespoon cookie scoop, place dough over each pineapple and cherry-topped well. Flatten dough gently with an offset spatula.
Bake: Bake in the preheated oven for 25 minutes, or until the cookie edges are golden brown and the brown sugar mixture is bubbling up the sides.
Cool and Unmold: Allow the cookies to cool for 10 minutes in the pan. Carefully invert onto a surface lined with wax paper to catch any sticky syrup. If pineapple slices stick, reposition them gently back onto the cookie tops.
Final Cooling and Storage: Let the cookies cool completely before serving. Store in an airtight container; best enjoyed within 2 to 3 days for maximum freshness.

Notes

Use wax paper during unmolding to catch the sticky caramelized sugar.
If pineapple slices stick to the pan, reposition them gently onto the cookie after turning out.
Cookies are best eaten within 2 to 3 days when stored in an airtight container.
Room temperature butter creates a smoother, more easily creamed dough.

Prep Time: 15 minutes
Cook Time: 25 minutes
Category: Dessert
Method: Baking
Cuisine: American

Keywords: pineapple upside down cookies, sugar cookies, pineapple cookies, caramel cookies, fruit topped cookies, easy dessert, mini cake pan cookie recipe