Ganache

1. Place the chopped chocolate in a large glass bowl. Place the cream in a pan over medium heat and bring just until it starts to boil/bubble around the edges. Pour the cream over the chocolate and let sit undisturbed for 5 minutes.
2. Using a whisk or rubber spatula slowly start to stir the cream and chocolate together until smooth and creamy. At this point, fold in the brownie pieces and optional bourbon. Allow to cool for 30 minutes then place in the fridge to cool completely. ~2 hours.
3. When the ganache is firm to the touch, scoop out a teaspoon of mixture and roll into a ball. Place on a parchment-lined pan and repeat. Once all of the balls have been formed, place them in the freezer until frozen. ~1 hour. At this point you can remove the pan, place the balls in a freezer bag until ready to use (or eat on their own!).

Cookies

1. Preheat the oven at 350F, rack in the middle. Line a cookie sheet with parchment. Set aside.
2. Place the 5 ounces semi-sweet chocolate and butter in a microwave safe bowl. Microwave in 30 second increments until fully melted and smooth. Set aside to cool slightly.
3. Sift together the flour, cocoa powder, espresso powder and salt into a bowl; set aside. In the bowl of a stand mixer fitted with the paddle attachment, beat the eggs, brown sugar and extract until well combined, scraping down the sides. ~5 minutes. Add in the melted chocolate mixture and slowly turn the mixer on to combine. Once the chocolate is all incorporated, slowly add in the flour mixture in small increments, scraping down the sides. It’s okay if it doesn’t all get blended it. A few streaks are OK.
4. Remove the bowl from the mixer and fold in the chocolate chips. At this point, remove the truffles from the freezer. *If your kitchen is hot, only remove a few truffles at a time.
5. With a medium cookie scoop (or 2 heaping tablespoon), form the dough into a ball and, using your thumb, press a cavity in the center. Place one truffle ball in the middle and form the cookie dough around it. Repeat and leave a 2” space between each cookie.
6. Bake for 8-11 minutes or until the sides are set and the top is still slightly soft. The cookie will firm up as it cools. You do not want to overbake these.
7. Cool on the pan for 5 minutes then carefully transfer to a cooling rack. Allow to cool completely before storing in an airtight container.