Begin by preheating your oven to 350 degrees F.
In a large bowl with your electric mixer on high, beat the butter until creamy. Then beat in the sugar and vanilla. Turn the mixer to low and beat in the flour until just incorporated.
Divide the dough into two parts. Place one half of the dough between two sheets of wax paper and roll it until it’s 1/4-inch thick. Then use a 2 1/2-inch-diameter round cookie cutter to cut the dough. Place the cut-outs on an ungreased cookie sheet. Repeat this process with the remaining half of the dough. (You can reform excess dough, roll it out, and cut it again until all the dough is used.)
Bake the cookies for 12 to 14 minutes or until set and just barely starting to brown. Transfer them to a cooling rack to cool completely.
While the cookies cool: In a microwave safe bowl, melt the unwrapped caramels and milk on high for 2-3 minutes, stirring every 30 seconds until the caramels are melted and the mixture is smooth.
Add1-2 teaspoons of the caramel mixture to each cookie. Then sprinkle the cookies with flake sea salt.
Finally, in another microwave safe bowl, melt the chocolate and butter on high for 1-2 minutes until it is smooth. Stir every 30 seconds. Drizzle the melted chocolate mixture over the cookies. Let the cookies cool until the chocolate sets.
Store the cookies in an airtight container.