Preheat the oven to 325 degrees. Line a 9x13 baking dish by with parchment paper and spray it with a nonstick baking spray.
In a large bowl, add the 2 cups butter, 1 1/2 cups powdered sugar, 1 cup granulated sugar, and 6 teaspoons vanilla extract. Beat with a hand mixer on medium until the butter is well combined.
Gradually add in the 4 cups all-purpose flour and beat until all of the flour is added. The shortbread will be crumbly but should hold it's shape when pinched together.
Take 3-4 cups of the shortbread dough and firmly press it into the bottom of your prepared pan.
Bake for 25 minutes or until the base is set and the edges are golden. Set aside to cool.
Pour the 14 ounce bag baking caramel bits and 1/3 cup heavy whipping cream into a saucepan and stir together on the stovetop until it’s all melted and gooey. Pour the caramel sauce over the cookie base and spread to the edges with an offset spatula.
Evenly sprinkle the 12 ounces semi-sweet chocolate chips all over the top of your caramel layer.
Using a small cookie scoop, scoop out dough balls from the remaining dough. Roll the dough into a ball and press it flat like a disc. Lay them over your chocolate chip layer allowing them to overlap a little.
Bake for 35-40 minutes until the top is golden brown. Set out at room temperature to cool completely.
Cut and serve.
Notes
Storage: Store covered or in an airtight container at room temperature for up to 5 days.