First, make the dirty chai sugar. In a small bowl, combine the granulated sugar, spices and black pepper. Set aside.
Next, make the cookies. In a stand mixer fitted with the paddle attachment, beat the butter, granulated sugar, and brown sugar on low speed to combine, then increase to medium-high and beat until light and fluffy, about 2 minutes.
Use a silicone spatula to scrape down the sides and bottom of the bowl, then add in the egg, egg yolk, Greek yogurt, and vanilla. Beat on medium-high until mixture is fluffy and pale in color, about 2 minutes.
Stop the mixer and scrape down the bowl, then add the flour, cinnamon, ginger, cardamom, espresso powder, cloves, black pepper, cream of tartar, baking soda, and salt and beat on low speed until just combined and no streaks of flour remain.
Use a 2 ounce cookie scoop to portion out equal amounts of dough. Roll each ball of dough in the dirty chai sugar until it’s evenly coated. Place the cookies on the prepared baking sheet, spacing them 3 inches apart.
Bake until the cookies have started to crackle on the top and are set and firm around the edges but still somewhat soft in the middle, 12 to 13 minutes. Remove the baking sheet from the oven and allow the cookies to cool completely on the baking sheet before serving.