I start by heating my oven to 350°F so it's fully ready by the time my batter is mixed. Then I lightly grease my 9x13 pan with baking spray or a little coconut oil. Skipping this step is asking for a stuck cake later.
Next, I prepare the boxed yellow cake mix exactly as the package directs, using the eggs, oil, and water it calls for. I pour this batter straight into my prepared pan and spread it into an even layer. I haven't baked it yet, but this is just the base.
In a separate large bowl, I whisk together the pumpkin puree, evaporated milk, heavy cream, eggs, brown sugar, and pumpkin pie spice. I keep whisking until it's completely smooth with no streaks of egg or sugar left behind.
This is the fun part. I slowly pour the pumpkin mixture all over the top of the unbaked cake batter, moving in a steady back-and-forth motion so it covers every corner. I don't stir it the layers separate on their own in the oven.
I carefully place the pan in the oven and bake for 50 to 60 minutes. I check for doneness by inserting a toothpick into the center; it should come out clean, and the middle shouldn't jiggle. The top may look a little darker than a normal cake, and that's completely normal.
Once it's out of the oven, I let the cake cool to room temperature right in the pan. Rushing this step means a melty frosting later, so I usually let it sit for at least an hour before touching it.
While the cake cools, I whisk the instant vanilla pudding mix with pumpkin pie spice and cold milk in a medium bowl until it starts to thicken. Then I gently fold in the Cool Whip with a spatula until it's fully combined and fluffy.
Finally, I spread the frosting evenly over the cooled cake. I like to chill mine for at least an hour before slicing so the layers set firmly and cut cleanly.