Add the instant vanilla pudding mix to a bowl. Add the milk and stir until mixed completely.
Place in the fridge and allow to sit for 5 to 10 minutes until it firms up slightly, but not completely.
Add in the rest of the pudding ingredients (pumpkin puree, Cool Whip, brown sugar, and spices. Mix well. Place back into the fridge for up to 45 minutes to chill.
Divide into individual bowls. Add optional whipped cream, a dusting of cinnamon, and cinnamon stick and serve.