Line a 8x8 baking dish with parchment paper making sure the sides are completely covered and some of the paper is sticking off the side, so you can pick it up later. Preheat the oven to 325°.
In a large bowl add the sugar and 1/2 stick of melted butter, mix with a hand beater until combined. Add in the salt and cocoa powder, beat again until completely mixed through.
Add in the eggs and vanilla and beat until combined. Add in the flour and mix with the beater until it’s all mixed together. Pour the brownie batter into the prepared baking dish.
Spread around evenly. Bake for 20-25 minutes.
In a small microwave safe bowl add the heavy cream and caramels, place in the microwave and cook for 30 seconds, stir and repeat until completely melted and smooth. Once the brownies are done pour the caramel on top of the brownies and smooth it out evenly.
Wait for the baking dish to cool a bit (about 10-15 minutes) and then place in the freezer for 25 minutes. Once the caramel is hard on top, remove from the freezer.
While you wait for the caramel to harden, make the cookie dough layer. To a large bowl add the brown sugar, sugar and 1/2 cup of room temp butter, mix using the hand mixer until it becomes light and fluffy.
Add in the heavy cream and vanilla, mix again. Add the salt and flour and mix. Sprinkle in the 1/2 cup of chocolate chips and mix once again. Remove the baking dish from the freezer and evenly spread the cookie dough layer all over top of the caramel layer.
In a medium sized microwave safe bowl add the oil and 8 oz of the chocolate chips. Microwave for 30 seconds and stir, repeat until melted. Pour the chocolate all over top of the cookie dough layer and spread. Place in the fridge until ready to serve. Slice and enjoy!