Line two large baking sheets with parchment paper or silicone baking mats and set aside.

Whisk together the flour, Dutch processed cocoa powder, salt, and baking powder in a medium size bowl.

Set aside.

In the bowl of a stand mixer fitted with the paddle attachment cream together the butter and both sugars on medium high speed until light and fluffy, about 2-3 minutes.

Add the egg yolk and the vanilla then beat again until completely combined. Scrape down the sides of the bowl as necessary.

Turn the mixer speed to low, then slowly add the dry ingredients, mixing until just combined.

Using a cookie scoop , drop mounds of cookie dough onto the prepared baking sheets until you have used up all of the dough.

Using a ¼ teaspoon measure, gently press down on the tops of the dough balls to create an indent.

If the spoon is sticking to the dough, dip it into some cocoa powder.

Once all of the cookie dough balls have been indented, chill in the refrigerator for at least 1 hour.

Preheat the oven to 350ºF

Bake the cookies no more than 8 to a baking sheet for 9 to 11 minutes until the edges are set.

Remove the cookies from the oven, then press down gently again with the ¼ teaspoon measure to re-shape the wells while the cookies are still hot.

Allow the cookies to cool for at least 5 minutes on the baking sheet before transferring to a cooling rack to cool completely before filling with caramel.

In a small bowl with a spout (preferably a glass measuring cup with a spout), combine the unwrapped caramels, 2 teaspoons of milk, and salt.

Melt in the microwave on high for 30 seconds, stir, then continue to microwave in 15 second intervals, stirring after each, until you have a smooth, pourable mixture.

Add an additional ½ teaspoon of milk if you need to thin it out more.

While the caramel is still very warm, slowly and carefully fill each chocolate cookie, taking care not to overfill the wells.

The caramel will spread to the edges, so only fill it about halfway before adding more to fill to the brim.

Allow the caramel to set before drizzling with chocolate.