In a large mixing bowl, beat butter and powdered sugar for several minutes until well blended. Add in flour, salt and vanilla. Beat for 2-3 minutes until dough starts to form a ball.
Drop dough onto a light floured surface. Using your hands, shape into a log, about the size of a paper towel tube. Wrap in plastic wrap and refrigerate at least 30 minutes.
Slice dough (about 1/5 inch thick) and bake on a parchment paper lined baking sheet. Bake in a 350 degree oven for 11-13 minutes, until edges set and begin lightly browning. Do not overbake.
While cookies are cooling, add caramel and whipping cream to a microwave safe bowl. Microwave for 1 minutes. Stir and heat again for 15-30 seconds. Stir until smooth. Using a small metal scoop, drop about 3/4 Tbsp of caramel into the center of each cookie. It will spread on it own.
Melt milk chocolate in a microwave safe bowl for 1 minute. Stir and heat an additional 15-30 seconds if needed. Frost the tops of each cookie and allow chocolate to set (about 30 minutes). Store in airtight container at room temperature. ENJOY.