Preheat oven to 350 degrees F.
In a large bowl, cream butter and sugar together.
Add vanilla, flour and salt and mix until well combined.
On a lightly floured surface, roll the dough out to 1/2 inch thick. With a small biscuit cutter, cut out cookies and place on a cookie sheet lined with parchment paper or a silicone liner.
Bake for 14-16 minutes, or until cookies are set and just beginning to brown on the bottom. Remove from oven and let cookies cool completely.
Combine caramel and evaporated milk in a microwave safe bowl and melt according to package directions. Spread over cooled cookies and let set.
In a small microwave safe bowl, melt chocolate chips and shortening in 30 second increments, stirring in between each increment until melted and smooth. Spread over the tops of cooled caramel.
And then your done!!