Preheat the oven to 325°F. Line two large baking sheets with parchment paper, lightly spray the parchment with non-stick spray, and set the sheets aside.
In a medium bowl, whisk together 1 cup plus 2 1/2 tablespoons all-purpose flour (do not pack the flour), 3 tablespoons unsweetened cocoa powder, 1 teaspoon baking powder, and 1/2 teaspoon salt. Set aside.
In a large, microwave-safe bowl, combine 6 ounces chopped semi-sweet chocolate and 2 tablespoons unsalted butter.
Microwave the chocolate and butter in 15-second increments, stirring between each increment, until the mixture is completely melted and smooth. Be careful not to overheat.
Whisk 1 1/2 teaspoons vanilla extract into the melted chocolate mixture. Then whisk in 1/4 cup packed light brown sugar, 1/4 cup granulated sugar, and 1 teaspoon orange zest until blended.
Beat in the 2 large room-temperature eggs one at a time, beating well after each addition until fully incorporated. Then beat in 2 tablespoons whole milk.
Add the dry ingredient mixture to the wet ingredients and stir gently until just combined—do not overmix.
Fold in 7 ounces chopped orange chocolate until evenly distributed. If you want to top the cookies after baking, reserve a few chocolate pieces before folding.
Using a 1/4-cup measure, scoop portions of batter onto the prepared baking sheets, spacing the scoops at least a couple of inches apart to allow for spreading.
Bake one sheet at a time on the oven’s middle rack: place the sheet in the oven, immediately reduce the oven temperature to 300°F, and bake for 16 to 19 minutes, or until the edges are set and the tops are dark and shiny.
If desired, press a few reserved chocolate pieces onto the tops of the warm cookies right after they come out of the oven.
Allow the cookies to cool completely on the baking sheet before transferring to a cooling rack or serving.