Line a baking sheet with a silicone mat or parchment paper and set aside.
Pour 1/2 c sugar into medium saucepan over medium heat. Heat sugar undisturbed until a light caramel forms around the edge (5 min). With a heat-resistant rubber spatula, gently stir, eliminating lumps, cooking to a smooth, amber color (3 min). Quickly add almonds and stir to coat. Caution: will be very hot.
Transfer almonds to prepared baking sheet and flatten with spatula, pressing nuts into caramel. Chill completely to create an almond praline. Can be made a day ahead.
Chop almond praline into small pieces with a knife. Place a layer of ladyfingers on the bottom of each jar/bowl/ramekin, cutting them to fit snugly. Drizzle each with 1/2 t or more of Amaretto.
In electric mixer bowl, add cream and 3 T sugar; whip just until peaks form. In separate mixing bowl, whisk together 2 T sugar, pumpkin, cinnamon, vanilla and salt. Add mascarpone and combine well. Gently add pumpkin mixture to cream and fold to combine. Add ½ c of praline, reserving the rest for garnish.
Spoon pumpkin cream over ladyfingers, filling just shy of half. Arrange another layer of ladyfingers, gently pressing into cream Drizzle with Amaretto and top with remaining pumpkin cream. Gently tap each dish against counter to fill any gaps.
Refrigerate a minimum of 4 hr, up to overnight. Sprinkle chopped praline on top and serve.