Adjust the oven rack to the middle position and preheat to 350°F. Line 2 large baking sheets with parchment paper.
In a microwave-safe bowl, melt the butter and chocolate together in 30 second increments until smooth. Stir in the vanilla and allow to cool slightly.
6 Tablespoons salted butter, 6.5 oz dark chocolate bar, 1 tsp pure vanilla extract
In a large bowl with an electric mixer or stand mixer with the whisk attachment, beat the sugars and eggs together until pale and very fluffy, 3-4 full minutes. When you lift the whisk out of the mixture, it should fall back into the mixture in thick ‘ribbon-like’ trails before disappearing into the batter.
3/4 cup granulated sugar, 2 large eggs, 1 large egg yolk
With the mixer running on low, pour in the chocolate mixture and beat on low until combined and no yellow streaks remain.
1 tsp pure vanilla extract
Stir together the cocoa powder, flour, baking powder, and salt. Gently fold until you get a smooth glossy batter, similar to brownie batter. Add the chocolate chips and stir to combine.
1 1/2 cups all-purpose flour, 1/4 cup Dutch-process cocoa powder, 1 teaspoon baking powder, 1/2 teaspoon salt
Use a medium (2 Tablespoon) cookie scoop to scoop out all of the dough out at once onto the prepared baking sheets. This makes about 16 cookies and they should fit comfortable on 2 baking sheets. You need to bake them all quickly for the best crackly glossy tops.
Bake in the preheated oven for 8-10 minutes (I did 8), until shiny and cracked on top but still soft in the center.
Directly from the oven you can use a round cookie cutter or rim of a glass to nudge and shape the cookies into a perfect circle. Immediately use the back of a small spoon (like a Tablespoon) to press a shallow indent into the center of each warm cookies. Allow the cookies to cool on the baking sheet for 10 minutes before transferring to a wire rack.
While they’re cooling, combine the caramels and heavy cream in a microwave safe bowl. Heat in 30 second increments until the caramels are full melted and smooth. Allow to cool slightly (5 minutes) to firm up so it’s pourable but thick enough to hold it’s shape.
11 oz soft caramels, 2 Tablespoons heavy cream
Spoon the caramel into the indent of each cookie. Sprinkle with flaky sea salt and let the caramel set, about 20 minutes.
Flaky sea salt