Chocolate-Topped Vanilla Cookie

"These cookies from Lisa Yockelson are made with rich chocolate frosting and crisp sugar cookies...."

INGREDIENTS
4 cups bleached all-purpose flour
1 teaspoon baking soda
1 teaspoon cream of tartar
1/2 teaspoon salt
1/2 pound unsalted butter, softened
1 cup plain vegetable oil (such as canola)
1 cup superfine sugar (or just blitz granulated sugar in a blender until finely ground but not powdery)
1 cup confectioners' sugar
4 large egg yolks
2 1/2 teaspoons vanilla extract
4 cups confectioners' sugar, or more as needed
1/8 teaspoon salt
6 ounces unsweetened chocolate, melted and cooled to tepid
2 1/2 teaspoons vanilla extract
1/2 cup plus 1 tablespoon milk, heated to tepid
8 tablespoons unsalted butter, softened
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