In a large mixing bowl beat brown sugar, peanut butter, butter, and sugar with electric mixer on medium speed until combined.
Add eggs, milk, and vanilla; beat well. Combine flour and baking soda; add to egg mixture and beat well.
Shape dough into 1 inch balls. Roll in the 1/2 cup sugar and place 2 inches apart on ungreased cookie sheets (we like to use parchment paper!).
Bake in 350-degree oven for 10 to 12 minutes or until lightly browned.
Let cool for 8-10 minutes and then press half of a peanut butter cup, cut side down, into each cookie, about 1/2 inch from bottom edges (cookies will crack a little…that's okay!).
Decorate with frosting to look like baskets!
