In the bowl of a stand mixer with the paddle attachment, beat the cream cheese until it's light and fluffy; about 3 minutes.
Add the pumpkin puree and pumpkin pie spice and mix until completely combined.
Scrap down the sides of the bowl.
Add the sweetened condensed milk, followed by the cheesecake pudding mix.
Mix again until everything is combined.
Change the paddle attachment to the whisk attachment and slowly add in the Cool Whipped Topping until well combined. You can also do this step by hand if you prefer.
Refrigerate the mixture until the pudding has firmed up. This should take about 30 minutes or so.
At this point you could store the mixture in an air-tight container and refrigerate till the next day.
Combine the crushed graham cracker crumbs in a bowl.
Add the melted butter and 4 tablespoons sugar.
Stir to combine.
Add the crumbs to the bottom of the cups you want to serve the dessert in.
Use the tart tamper to press the crumbs down into the bottom of the cup.
Using a cookie scoop, add a few scoops of cheesecake pudding on top of the graham cracker crumbs.
Top the pumpkin cheesecake pudding with homemade whipped cream or a dollop of whipped topping on top.
Then sprinkle chopped pecans and a few graham cracker crumbs.
Notes
Depending on the size cups you use for this dessert, you should be able to get 8 to 10 servings.