In a large mixing bowl, combine the pumpkin puree, milk, vanilla pudding mix, pumpkin pie spice, and vanilla extract until smooth and well combined.
Using a hand mixer on low speed, mix in the thawed Cool Whip until incorporated.
In six dessert cups or ramekins, add 2 tablespoons of graham cracker crumbs to the bottom of each cup.
Evenly distribute the pumpkin pie filling across the six cups. Smooth the pumpkin filling down with the back of a spoon.
Chill for 1 hour before serving for the best flavor. Top with whipped cream and a light sprinkle of cinnamon.
Notes
Storage: Store leftover pumpkin pie cups in the refrigerator, covered with plastic wrap, for up to 3 days. If making ahead, add the whipped cream topping just before serving to keep it fresh.