Prep a cookie sheet with a sheet of parchment paper and set aside.
In a separate small bowl, whisk together the flour, cocoa, and salt. Set aside.
In a stand mixer fitted with a paddle attachment, cream together the butter and sugar until it’s light and fluffy. Add in the egg yolk, milk, and vanilla. With the mixer on low speed, mix in the flour/cocoa/salt mixture until just combined. Don’t overmix. Chill dough for an hour in the refrigerator.
Preheat the oven to 350 degrees.
In a small bowl, whip up the egg whites until they’re bubbly and foamy.
In another separate bowl, add in the pecans.
One by one, scoop up the chocolate cookie dough with a small cookie scoop, roll the dough into an even ball, roll the cookie dough ball in the foamy egg whites, then in the pecans until they stick. Set onto the prepared cookie sheet. Repeat with all the dough.
Using the rounded end of a circle-shaped measuring spoon or a small round end of a melon baller, press the curve into the cookie to create a crater in each cookie dough ball.
Bake for 10-12 minutes, then use the back of the melon baller to create the crater again (cookies like to flatten a bit and creating the crater again will make space for our caramel pool in the middle).
Add the melted caramel to a squeeze bottle (likely used for ganache, etc) and squeeze in a pool of caramel once the cookies have cooled.
Add the melted chocolate to another squeeze bottle, piping bag, or plastic baggy, and drizzle on a bit of the melted chocolate chips. Place in the freezer for 5 minutes to set.
Store in an airtight container for up to a week for maximum freshness. Enjoy!