In a separate bowl, toss granulated sugar and cinnamon together; set aside.
On a sheet of parchment paper or wax paper dusted with flour, roll half of the biscuit dough at a time into a large rectangle.
Brush rolled dough liberally with buttermilk and sprinkle with half of the sugar mixture and half of the chocolate chips, keeping one long edge of the dough wet but clean of other ingredients so that the roll will seal.
Carefully roll the dough into a tight log and slice with a serrated knife into one inch thick slices.
In your well-greased pan, coat the bottom with approximately 1/2 inch of caramel and place the slices of biscuit roll into the mixture, nestling them into the caramel and taking care to not overcrowd the pan.
Repeat with remaining half of dough.
Bake for approximately 20 minutes in the preheated oven or until golden brown.
Carefully invert the pan of sticky biscuits onto a serving platter, sprinkle with confectioners sugar and enjoy while they’re warm!