In a mixing bowl, whisk together the flour, cocoa powder, and salt.
In a separate bowl, or bowl of a stand mixer, beat the butter and sugar together until light and fluffy. Add the egg yolk, milk, and vanilla extract and mix until combined. Mix in the dry ingredients. The dough will be stiff. Wrap the dough in plastic wrap and refrigerate for one hour.
In a bowl, whip together the egg whites until frothy (I used a food processor). Add the chopped pecans to a separate bowl. Use a 2 tablespoon cookie scoop to measure the dough and roll into a ball. Dip the dough in the egg whites, then roll in the pecans. Place on a parchment paper-lined baking sheet, 2 inches apart.
Use the back of a ½ teaspoon measuring spoon to make a well in the top of the cookies.
Bake at 350 degrees, for 11-12 minutes. Remove from the oven and allow to rest on the baking sheet for 2-3 minutes. While they are resting, use the measuring spoon to indent once again. Transfer the cookies to a cooling rack.
Unwrap and add the caramels and heavy cream to a microwave-safe bowl. Heat in the microwave for 1-2 minutes, stirring every 30 seconds, until melted and combined. Add ½ teaspoon of caramel to the indent of each cookie.
Melt the chocolate chips in the microwave at 50% power, stirring every 30 secons. Add to a ziplock bag and drizzle over the cookies.