Set oven rack in center of oven. Preheat oven to 350-degrees F. Line 2 large baking sheets with baking parchment, set aside.
In medium bowl, whisk together the flour, cocoa powder, baking soda and salt. Set dry ingredients aside.
In the bowl of a stand mixer, or using large mixing bowl and hand-held mixer, beat butter with Sugar In The Raw on medium speed until butter is pale and fluffy; mixture will be grainy. Beat in egg and Monk Fruit In The Raw just until combined. Add dry ingredients and mix until completely combined; dough will be dense and dry. Add milk, vanilla, peppermint extract and mix until dough is moist and sticky. Mix in chocolate chips by hand.
Place 30-inch piece of wax paper on work surface. Turn dough out onto paper and shape it into 10-inch disk. Wrap and refrigerate until dough is firm enough to handle, 1-2 hours. Dough may be refrigerated up to 24 hours and set at room temperature to soften slightly.
To shape cookies, break off walnut-size piece of dough and roll between your hands into a 1 1/2-inch ball. Repeat with remaining dough, setting balls on prepared cookie sheets, 2 inches apart. With your fingers, flatten balls into 2-inch rounds. If desired, for shiny finish, moisten your fingers slightly with water and smooth cookie tops and sides.
Bake cookies, one sheet at a time, for 10-12 minutes, until edges are firm. If garnishing, immediately sprinkle tops of soft cookies with crushed peppermint candy, pressing gently. Cool cookies for 2 minutes on the pan, then transfer to wire rack. Repeat with the second pan of cookies.
Peppermint Brownie Cookies are best served warm. Leftovers can be stored in airtight container for up to 24 hours.