In a large mixing bowl, beat softened 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 ⅕ 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 ¾ 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.
Store cookies in airtight container for up to one week.
Use regular kraft caramels if you can't find the "bits."