These Caramel Chocolate Chip Thumbprint Cookies are soft, buttery cookies filled with melted caramel and topped with a drizzle of milk chocolate. Perfect for Christmas cookie trays, holiday parties, cookie exchanges, or everyday baking.
In a large mixing bowl, whisk together the all-purpose flour and salt. Set aside.In a separate bowl, beat the softened butter and granulated sugar for 1–2 minutes until light and fluffy. Add the egg yolks and vanilla extract, then mix until everything is combined.Gradually add the flour mixture and mix until a soft cookie dough forms.
Line a baking sheet with parchment paper.Roll the dough into approximately 1-inch balls and place them on the prepared baking sheet. Use the back of a 1/4- or 1/2-teaspoon measuring spoon to gently press an indentation into the center of each cookie.Place the shaped cookies in the refrigerator for 1 hour to chill.
Preheat your oven to 350°F.Arrange the chilled cookies about 2 inches apart on the baking sheet. Bake for 14–15 minutes, or until the edges are lightly set.Remove from the oven and let the cookies cool completely. If the centers puff up while baking, gently press them again while the cookies are still warm.
Place the caramel bits and heavy cream in a microwave-safe bowl.Microwave for 1 minute, then stir. Continue heating in 30-second increments, stirring between each round, until the caramel is melted and smooth.Carefully spoon or drizzle a little caramel into the indentation of each cooled cookie.
Place the milk chocolate chips in a microwave-safe bowl. Microwave in 30-second increments, stirring well between each round until completely melted.Transfer the melted chocolate to a piping bag and snip off a small tip.Drizzle the chocolate over the caramel-filled cookies.
Step 6: Let the Toppings SetPlace the cookies in the refrigerator for about 1 hour, or until the caramel and chocolate have set.Once everything is firm, they’re ready to enjoy!