Preheat the oven to 315F. Line 2 half sheet pans (large baking trays) with parchment paper or silpat liners.
Whisk together the butter, brown sugar, molasses, milk, egg yolk, and vanilla in a large bowl.
Stir in the flour, baking soda, salt, ginger, cinnamon, nutmeg, cloves, and black pepper until well combined.
Scoop the cookie dough into 1 1/2-teaspoon sized balls and roll each in sugar.
Arrange the sugar coated cookie dough balls on the prepared baking trays about 1 1/2 inches apart.
Bake until the cookies are golden and crinkly looking, about 20 minutes, rotating the trays once halfway through.
As soon as the cookies come out of the oven, use a glass to press down on the top of each cookie to flatten.
To let the cookies crisp completely, let them cool before serving.