Toss the graham crackers into a food processor or blender and pulse until they’re fine crumbs. Add melted butter, sugars, and cinnamon. Give it a few more pulses until everything is combined.
Spoon about 3 tablespoons of the crust mixture into each jar or cup. Press it down gently. You can set a little aside if you want to sprinkle some on top later.
In a stand mixer with the paddle attachment, beat the softened cream cheese for 2 minutes. Scrape the sides and add the pumpkin, pumpkin pie spice, pudding mix, and condensed milk. Mix until smooth and creamy.
Use a spatula to gently fold in the whipped topping until just combined. Don’t overmix.
Divide the filling evenly between your jars on top of the crust.
If you’re serving right away, add a swirl of whipped cream and a sprinkle of those extra graham crumbs. If you’re making them ahead, just pop them in the fridge and add the toppings right before serving.