To make the gingerbread shortbread pieces, begin by creaming together the butter, powdered sugar and brown sugar until light and fluffy, about 1 minute. Mix in the molasses and vanilla. Add the flour and spices and stir until the dough comes together. Wrap the dough into a disk with plastic wrap and chill in the freezer for 15 to 20 minutes.
Preheat oven to 350°F. Line two baking sheets with parchment paper and set aside.
Transfer the chilled dough onto a lightly floured work surface and roll out to 1/2-inch thick. Cut into 1-inch squares and transfer to the baking sheets. Bake until golden brown and crisp around the edges, about 18 to 20 minutes. Remove from the oven, reduce temperature to 250°F and allow the cookie pieces to cool completely. Remove the cooked onto a plate or bowl and spray the parchment-lined baking sheets with cooking spray and set aside.
Meanwhile, let's make the caramel corn. Place a very large, heavy-bottomed pot over medium heat with the oil. Once hot, add the kernels and spread out evenly and cover with a tight fitting lid. Allow to cook, shaking the pan ever so often, until the kernels have popped, about 8 to 10 minutes.
Transfer the popped corn to the largest bowl you have. Wipe the pot clean and return to medium heat. Add brown sugar, butter, corn syrup, molasses, and spices and cook, stirring constantly until the mixture comes to a boil. Allow to cook, without stirring, for 4 minutes.
Remove the pot from the heat and stir in the baking soda and vanilla. The mixture will bubble up, but keep stirring until thickened and smooth. Immediately pour over the popped corn and stir until evenly coated. Divide between the two prepared baking sheets, spreading out into an even layer.
Bake for 1 hour, tossing every 10 to 15 minutes. Let cool completely in the pans. Then break up any large bits. Drizzle with the melted chocolate and then top with the gingerbread cookie bits. Store in an airtight container, at room temperature, for up to 5 days. Enjoy!