For the Brownie Layer

1. Preheat the oven to 350°F. Generously grease a 9×13-inch baking pan and line it with parchment paper.
2. In a medium-sized mixing bowl, combine the granulated sugar with the oil, milk, and vanilla extract and beat together until well combined.
3. Next, add the eggs and beat just until combined, about 30 seconds or so.
4. Combine the dry ingredients in a separate bowl and stir to combine. Add the dry ingredients to the batter and mix just until combined. Fold in the chocolate chips with a spatula.

For the Pumpkin Layer:

1. In a large mixing bowl, beat the cream cheese until free of lumps then add the sugar and beat on low speed until completely smooth, scraping down the bowl occasionally. Next, add the pumpkin puree and beat until well combined.
2. Finally, add the egg, vanilla extract, and pumpkin pie spice and mix on low speed until well combined. Scrape down the bowl as needed.

To Assemble:

1. Spread the 2/3 of the brownie batter in the prepared pan. Then spoon 2/3 of the pumpkin filling over the brownies. Finally, spoon the remaining brownie batter and pumpkin filling on top and swirl with a knife.
2. Bake at 350°F for 34-38 minutes. The toothpick should still have some crumbs on it but not be wet or glossy. Remove from the oven and allow to cool prior to cutting. Store in an airtight container.