Stir in the coffee mixture and the butter mixture in the bowl of an electric stand mixer. Mix until combined. Gradually add sifted ingredients, mixing until combined.
Chill dough for at least 30 minutes.
Preheat oven to 375 degrees F. Grease or line 4 baking sheets with parchment paper.
Using a 1-1/2 tablespoon scoop, place cookies onto baking sheets.
Bake for 8 minutes or until the edges are slightly brown. Remove the cookies from the pan put them on a cooling rack. Let the cookies cool completely.
In a medium saucepan, combine condensed milk and brown sugar. Bring to a boil over medium-high heat, whisking constantly. Reduce heat, and simmer for 5 minutes, whisking constantly.
Remove from heat and whisk in butter and vanilla.
Spoon hot caramel over cooled cookies. When cooled, the caramel will set and be difficult to spoon so wait to make the caramel when the cookies have cooled.
In a glass bowl, melt butter in the microwave. Add remaining ingredients and mix on low until blended. Turn on high and blend for another minute or until smooth. Drizzle with a fork, piping bag or a squeeze bottle. Allow drizzle to set.
Cookies were adapted from a local radio program in 1949! Caramel Adapted from Lady Behind The Curtain blog
This recipe was calculated using the exact brands and measurements I used to make this recipe. If you are following a strict diet please note changing anything will cause the nutritional info to change. My calculations are intended as a guide only.