Begin by preheating your oven to 350°F. In a microwave-safe bowl, melt the unsalted butter on high until fully liquefied. Add the semisweet chocolate chips and sweetened condensed milk, microwaving in intervals, stirring every 30 seconds, until the chocolate is completely melted and the mixture is smooth. Incorporate the vanilla extract, followed by the all-purpose flour, mixing until well combined. Finally, fold in the toasted chopped pecans and caramel bits.

Using a tablespoon, drop the dough onto parchment-lined baking sheets, spacing them two inches apart. Bake in the preheated oven for approximately 7 to 9 minutes, or until the edges are set. Once baked, allow the cookies to cool on the pans for 2 minutes before transferring them to wire racks to cool completely.

For the icing, melt the semisweet chocolate chips and shortening together in the microwave on high until smooth, then drizzle this mixture over the cooled cookies. Store the finished cookies in an airtight container to maintain their freshness.