To make the filling, place all dry ingredients in a saucepan and whisk to combine. Then add pumpkin purée and whisk again. Slowly pour in milk and stir again until well combined.
Place over medium heat and bring to a low bubble – not boil – whisking often. Once it starts bubbling and getting thick, reduce heat to medium-low and continue cooking until a visible ribbon forms when spooning it across the top. It should be thick and kind of jiggly. During this process switch to a rubber spatula for stirring to ensure the pudding is not sticking to the bottom or sides of the pan.
Remove from heat and add vanilla and whisk. Let set for 5-10 minutes, then transfer to a glass bowl and cover with plastic wrap, making sure the wrap touches the pudding – otherwise a film will form.
Refrigerate for several hours or until completely chilled and set.
While the pudding is setting, crush your graham cracker crumbs or prepare your crust. Set aside.
Prepare your coconut whipped cream- chill in the fridge until serving.
To assemble, gather 6-8 small glasses and fill with a healthy spoonful of graham cracker crumbs or crust (about 3/4 inch high - see photos). Next divide pudding evenly among cups and top with whipped cream. Sprinkle with a little pumpkin pie spice and serve immediately. Cover with plastic wrap to store for later. Will keep for a couple days.