Preheat the oven to 350°F.
In a large bowl, use a hand mixer to cream butter (room temperature) and cashew butter together.
Mix until combined. Scrape down the sides of the bowl and add the brown sugar, sugar, peppermint extract and vanilla. Beat again until fluffy.
Add in the egg and milk. Beat again.
Pour all of the dry ingredients in with the wet ingredients: baking soda, salt, cocoa powder, and flour. Use the hand mixer to beat everything together. It will be thick but soften up as everything becomes mixed.
Once the dry ingredients are combined, switch from the hand mixer to a rubber spatula. Continue to fold the batter until it’s a shiny, chocolatey color.
Use a cookie scoop to scoop cookies. Shape into a ball with your hands and dip each of the cookie dough balls into a bowl of sugar.
Place each chocolate peppermint cookie on the baking sheet, lined with parchment paper.
Bake for 9-12 minutes or until the centers are set. DO NOT OVERBAKE.
While cookies are baking, unwrap the peppermint kisses.
Immediately after removing the cookies from the oven, press a candy kiss in the center of each cookie. Remove from the baking sheet after 2-3 minutes and onto a wire cooling rack.
Let come to room temperature and enjoy!