Prep your tools and oven: Heat the oven to 350°F (175°C).
Line two baking sheets with parchment paper. Unwrap the chocolate kisses and set them in a bowl so they’re ready to go.
Mix dry ingredients: In a medium bowl, whisk 1 1/2 cups all-purpose flour, 1 teaspoon baking soda, and 1/4 teaspoon salt. Set aside.
Cream the butter and sugars: In a large bowl, beat 1/2 cup unsalted butter (softened), 1/2 cup creamy peanut butter, 1/2 cup granulated sugar, and 1/2 cup packed light brown sugar until light and fluffy, about 2 minutes.
Add egg and flavorings: Beat in 1 large egg, 1 teaspoon vanilla extract, and 1 tablespoon milk until smooth.
Combine wet and dry: Add the dry ingredients to the wet and mix on low until just combined.
The dough should be soft but not sticky.
Chill briefly: Cover the bowl and chill the dough for 20–30 minutes. This helps the cookies hold their shape and prevents over-spreading.
Shape and sugar-coat: Roll the dough into 1-inch balls (about 1 tablespoon each). Roll each ball in granulated sugar to coat and place on the prepared sheets, leaving 2 inches between them.
Bake: Bake for 8–10 minutes, until the edges are set and the tops are slightly cracked. They should still look a bit soft in the center.
Press the kisses: Remove the cookies from the oven.
Immediately press a chocolate kiss into the center of each cookie. The edges will crack slightly—that’s perfect.
Cool: Let the cookies sit on the baking sheet for 5 minutes to let the chocolate soften and set into the cookie. Transfer to a wire rack to cool completely.