Combine the pudding and milk in a large bowl. Whisk for about 2 minutes until thick. Fold in softened cool ship until smooth using a spatula. Layer the bottom of a 9 by 13 pan with graham crackers. Pour in half of the pudding mixture even on top. Lay another layer of graham crackers. Pour the remaining pudding mixture on top. Finish with one more layer of graham crackers.
Evenly spread the chocolate frosting over the graham crackers until dessert is fully covered. Put in the refrigerator and allow to chill. Ideally made a day in advance.
Notes
Katie's Tips:*This dessert gets better as it sits so make a day in advance if you have time.*The cool whip will soften if left on the counter for 30 minutes.*You may have to break a few of the graham crackers to make them fit into the pan. You will not notice once the dessert is frosted and served.