01 - Preheat the oven to 350°F. Line two baking sheets with parchment paper.
02 - Whisk together the all-purpose flour, baking soda, and salt in a medium bowl.
03 - In a large bowl, blend the melted and cooled butter with light brown sugar and granulated sugar until smooth.
04 - Add the eggs and pure vanilla extract to the butter-sugar mixture and beat until fully combined.
05 - Gradually add the dry ingredients to the wet mixture, stirring until just combined.
06 - Fold in the semisweet chocolate chips evenly throughout the dough.
07 - Scoop tablespoon-sized portions of dough onto the prepared baking sheets, spacing them two inches apart.
08 - Bake for 10 to 12 minutes until the edges turn golden. Transfer cookies to a wire rack and cool completely.
09 - Melt butter in a saucepan over medium heat. Stir in packed light brown sugar and cook for two minutes.
10 - Pour in whole milk and bring the mixture to a gentle boil, stirring constantly. Remove from heat and cool for five minutes.
11 - Gradually whisk in sifted powdered sugar and a pinch of salt until smooth and spreadable.
12 - Spread a layer of caramel frosting over each cooled cookie. Allow the frosting to set before serving.