To prepare the cookie dough

1. Preheat the oven to 350 degrees.
2. Combine flour, cocoa powder, and salt in a small bowl. Set aside. In a separate small bowl, combine the cream, vanilla, and espresso powder. Stir to combine and continue preparing the dough.
3. In the bowl of a stand mixer, cream together the butter and sugar until light and fluffy, about 2 minutes. Add the egg yolk and beat to combine. Scrape the sides of the bowl. Add the cream/vanilla/espresso mixture and beat to combine. Add the dry ingredients and stir just until combined.
4. Scoop out 2 teaspoons sized (about 3/4 inch balls) of dough and roll in hands into a ball. Toss the balls in the sugar until well coated and then place them about 2 inches apart on a sheet pan lined with parchment paper. Using the rounded back of a 1/2 teaspoon measuring spoon, lightly press “thumbprints” in the centers of each ball to create a cratered round of dough. Bake in the preheated oven until the edges are set, about 10 minutes. Remove from oven and gently pat dough the centers of the puffed dough with the measuring spoon again if needed to maintain a cratered center. Allow to cool on a cooling rack.

To prepare the coffee caramel

1. Stir to combine the heavy cream and espresso powder in a measuring cup. Set aside
2. Evenly spread the sugar in the bottom of a large non-stick pan over medium-high heat. Stir occasionally while the sugar is melting, incorporating all the clumps of sugar. After about 6-7 minutes, the sugar should have evenly melted. Allow to brown to a dark amber color and then reduce the heat to medium-low. Add the butter chunks and stir until melted and combined. Next, carefully add the heavy cream in a slow stream, stirring constantly. Cook for 1 minute and then remove from the burner. Stir in the salt and the pour into a heat proof container (I use a mason jar) and allow to cool.

To assemble the cookies

1. Melt the chocolate in a double boiler or a heat proof bowl over a pot of simmering water. Set aside once melted.
2. Fill each round of cookie with caramel (about 1/2 teaspoon). Melt caramel in 15 second intervals in the microwave, if needed, in order to get to the best consistency. Allow the caramel to set up slightly before drizzling with the melted chocolate.