Photo: Victor Protasio; Prop Styling: Heather Chadduck Hillegas; Food Styling: Torie Cox
Active Time
45 Mins
Total Time
3 Hours 50 Mins
Yield
40

Holiday cookie baking can be impressive without being stressful. Make this easy cookie dough and store it in the fridge up to two days before you need to bake these fantastic filled cookies. What's great about this recipe is that you'll stand apart at the annual cookie exchange. Not only are your cookies a different shape, but they are filled with ooey-gooey caramel and topped with a crunchy pecan and a little sea salt for the perfect mix of sweet and salty. 

How to Make It

Step 1

Prepare the Chocolate Sugar Cookie Dough:  Beat butter and sugar with a heavy-duty electric stand mixer on medium-high speed until light and fluffy, about 3 minutes. Add eggs and vanilla. Beat on medium until combined, stopping to scrape down sides of bowl as needed.

Step 2

Stir together flour, cocoa, baking powder, and salt in a medium bowl. With mixer running on low speed, add flour mixture to butter mixture, beating until just incorporated.

Step 3

Shape dough into a disk, wrap tightly in plastic wrap, and chill at least 2 hours or up to 2 days.

Step 4

Prepare the Cookie Cups: Divide dough into 40 (1-Tbsp.) balls. Place 1 ball in the cups of 2 (24-cup) lightly greased miniature muffin pans. (You’ll fill only 40 cups.) Using a teaspoon measure, press dough into bottom and up sides of muffin cups. Chill 20 minutes.

Step 5

Preheat oven to 350°F. Bake in preheated oven until cookies are dry to the touch and shape is set, about 10 minutes. Immediately press cookies again with teaspoon. Cool cookie cups in pans on a wire rack 5 minutes. Transfer cookie cups to wire rack to cool completely, about 30 minutes.

Step 6

Meanwhile, beat butter, cream cheese, and 2 tablespoons jarred caramel sauce with a heavy-duty electric stand mixer on medium speed until creamy, 1 to 2 minutes. Reduce speed to low, and, with mixer running, gradually add powdered sugar, beating until smooth. Beat in vanilla extract and flaky sea salt.

Step 7

Transfer filling to a piping bag fitted with a large star tip, and evenly pipe into cooled cookie cups. Drizzle about 1 tsp. jarred caramel sauce on each filled cookie cup. Sprinkle each cookie with desired amount of flaky sea salt, and top each with a toasted pecan half.