Line two sheet pans with parchment paper and heat the oven to 360°F (182°C).
Whisk together the flour, baking powder, and salt in a medium bowl; set aside.
In a large mixing bowl, beat the softened butter, sugar, and lemon zest on medium-high until very light and creamy, 2 to 3 minutes.
Beat in the egg, then the yolk, followed by the vanilla, scraping the bowl as needed.
On low speed, add the dry ingredients in two additions, alternating with the milk (begin and end with dry). Mix just until no dry streaks remain; do not overmix.
Let the dough rest for 10 minutes to hydrate. Meanwhile, prepare a large 2–3 tablespoon scoop and a small bowl of water for smoothing.
Scoop 12–14 mounds onto the prepared pans, spacing about 3 inches apart. Lightly dampen your fingertips and smooth each mound into a gentle dome about 2 1/2 to 3 inches wide.
Bake 12 to 14 minutes, rotating pans halfway, until the cookies are set and just barely golden at the edges while still pale on top.
Cool on the pans for 5 minutes, then transfer to a wire rack. For a classic flat surface, flip each cookie upside down so the flat side faces up and let cool completely.
Make the icings: In a bowl, whisk the powdered sugar, 1/4 cup milk, and vanilla until smooth and thick but spreadable. Scoop half into a second bowl and whisk in the cocoa, adding 1–3 teaspoons more milk until the chocolate matches the white icing in consistency.
Using an offset spatula, spread white icing over one half of the flat side of each cookie. Let stand 10 minutes (or chill briefly) to set the first half.
Finish with the chocolate icing on the other half, slightly overlapping the white edge for a crisp line. Allow cookies to set at room temperature for 30 minutes before serving.