In a large bowl, use an electric mixer (or you may use a stand mixer) to beat together butter and sugars until light and fluffy.

Add egg yolk and vanilla extract and stir well.

In a separate bowl, whisk together flour, cocoa powder, and salt.

With mixer on low-speed, gradually add flour mixture to butter mixture until completely combined. Be sure to scrape the sides and bottom of the bowl. The dough will be crumbly at first but as you stir it will cling together. This is a dry, stiff dough by design.

Once dough is clinging together, scoop and roll into 1 ½ Tablespoon-sized balls. Place on a wax-paper lined plate or baking sheet and use your thumb or the rounded end of a teaspoon to indent each cookie. Transfer cookies to freezer for 10-15 minutes to help keep them from spreading too much when they bake. Meanwhile, preheat oven to 350F (175C).

Once oven is preheated, place cookies on parchment paper lined baking sheet spacing at least 2” apart. Bake on 350F (175C) for 10-11 minutes. Immediately after removing from the oven, gently re-indent each cookie with the rounded back of a teaspoon (don’t use your thumb here, the cookies are hot!).

Allow cookies to cool completely on baking sheet before filling. While they cool, prepare your caramel.

Combine caramel and cream in a small saucepan over medium-low heat. Stir frequently until caramel is melted and mixture is smooth (alternatively you may do this in a microwave-safe bowl in the microwave, heating in 30-second intervals until melted).

Spoon melted caramel into cookie indents, filling to the brim but taking care to not overfill. Immediately after filling, sprinkle pecan pieces over the caramel. Repeat until all cookies are filled.

Drizzle cookies with melted chocolate. Allow caramel to cool and chocolate to harden before enjoying.