Preheat your oven to 350 degrees. Line two baking sheets with parchment paper and set aside.
Add your butter and sugar to a bowl and mix on high for five minutes until the mixture is light and fluffy.
Mix in your vanilla and eggs.
Add in the dry ingredients and mix until just combined.
Use a scoop to portion out the cookies between the two cookie sheets.
Bake your cookies for 7-10 minutes until the edges are just golden.
Remove from the trays and allow to cool completely on baking racks.
While the cookies are cooling add the sweetened condensed milk to a saucepan over medium heat. Allow it to cook for 5 minutes until lightly golden blond. Let cool.
Use a double boiler or microwave to melt the chocolate.
Scoop a small amount of the caramel into the center of each cooled cookie.
Drizzle the melted chocolate over the top of the caramel filled cookies.