Microwave milk at HIGH 3 minutes. Stir in 1/2 cup ground coffee, and let stand 10 minutes.
Pour coffee mixture through a fine wire-mesh strainer into a large bowl, discarding coffee grounds; let mixture cool completely.
Whisk together coffee mixture, sour cream, and pudding until thickened. Spoon into serving bowls; top evenly with whipped topping, and, if desired, serve with cookies.
Note: For testing purposes only, we used Pepperidge Farm Chocolate-Hazelnut Cream-Filled Pirouettes for the chocolate-hazelnut cream-filled cookies.