Whisk together the egg yolks and sugar until well combined and lighter in color. Set aside.
In a small saucepan, combine milk, pumpkin puree and 2 tsp pumpkin pie spice.
Heat over medium heat stirring often. Once the mixture just begins to bubble, remove from the heat.
Temper the egg mixture by adding ⅓ of the pumpkin mixture to the egg mixture and whisking constantly.
Add in the remaining pumpkin mixture scoop by scoop and continue to whisk until it is all combined and smooth.
Transfer the mixture back into the saucepan, and over medium heat. Continue to stir constantly as it reaches boiling. It does not take long for the mixture to thicken once it boils.
Once the mixture is thick and smooth custard - remove from the heat and transfer it to a bowl. Cover the mixture with plastic wrap that touches the surface of the custard. Allow to cool for 2-4 hours.
Once the pumpkin custard is chilled, combine with the softened cream cheese. Set aside.
In the bowl of a stand mixer, combine heavy whipping cream, vanilla, and powdered sugar. Whip on high speed for 2-3 minutes or until stiff peaks form. Do not over-whip. Set aside.
In a shallow bowl, combine the espresso and Kahlua, if using.