Make the Cupcakes: Preheat oven to 350°F (175°C) and line a cupcake pan. Whisk dry ingredients. Cream butter and sugar, beat in eggs and vanilla, and alternate dry ingredients with milk. Bake for 18–20 minutes and cool.
Make Cookie Dough Filling: Heat-treat the flour. Cream butter and sugar, mix in vanilla, flour, salt, and milk, then fold in chocolate chips.
Fill Cupcakes: Core the cooled cupcakes and fill with cookie dough.
Make Frosting: Beat butter, add powdered sugar, mix in heavy cream, vanilla, and salt. Frost cupcakes.
Decorate: Garnish with mini chocolate chips or cookie crumbs.