Preheat oven to 350F. Line a 9×13” glass pan with parchment paper with a 1” overhang. Spray the parchment with cooking spray.
Mix the carrot cake mix, pumpkin puree, and milk in a bowl with a wooden spoon. The mixture will become creamy. Add in the cinnamon chips and mix to combine. Spread the batter into the pan.
Bake for 25-35 minutes or until a toothpick comes out clean (a few crumbs are OK). Place the pan on a cooling rack. Wait 10 minutes and poke holes every 2” in the cake using the handle of a wooden spoon.
Pour the condensed milk over top of the entire cake. Wait 10 minutes and then pour the caramel sauce over top of the entire cake evenly. Allow to cool completely to room temperature. ~60-90 minutes.
Place the cake in the refrigerator, uncovered for 6 hours though overnight is better.
In bowl add in the cream cheese and butter. Using an electric mixer cream together the cream cheese and butter. ~2-3 minutes. Add in the confectioners’ sugar and vanilla and mix together on low so as to not blow the sugar everywhere. Once the sugar is incorporated add in the heavy cream and whip until fluffy. Remove the cake from the fridge and spread the whipped frosting on top of the caramel.
Place back in the fridge and allow to chill for 1 hour prior to serving.