Place oven rack in the center of the oven and preheat to 325. Line 3 baking sheets with parchment paper or wax paper. Whisk flour, cocoa, baking powder, baking soda and salt together in a bowl.
Combine the unsweetened chopped chocolate and the butter together in a mug and microwave on ½ power until melted - 2-3 minutes - if the butter becomes hot - allow it to cool before proceeding.
Whisk brown sugar, eggs, espresso powder and vanilla together in a larger bowl. Add the melted butter and chocolate mixture and mix until it becomes thick.
Fold in the flour mix into the egg mixture – this is difficult to mix and the powdered chocolate will want to float on the top of the more liquid mix. Just keep stirring it will eventually come together. Once all of the dry streaks are gone – allow the mixture to set for at least 10 minutes.
Place granulated sugar and powdered sugar onto saucers – Use a #30 scoop so that the cookies come out the same size. Scoop out the cookie dough and drop onto the granulated sugar – roll around and coat – then move to the powdered sugar – and roll around and coat so that there is an even thin coat of powdered sugar on the cookie ball.
Place the cookie balls onto the lined baking sheet – 11 per sheet. This recipe makes 27 cookies – so three sheets will be needed.
Bake cookies one sheet at a time – check at 11 minutes. The cookies will be puffed and cracked with the darker cracks looking raw. Let cool completely before trying to remove from the cookie sheet.
Notes
Make sure to serve with a napkin! These can be a little messy.