Step 1: In the bowl of an electric mixer, beat cream cheese and 1/3 cup sugar (or more) until light and fluffy, about 2 minutes. Slowly add in 1 1/2 cups heavy cream and beat until stiff peaks form.
Step 2: In another medium bowl, beat milk, pudding mix, pumpkin, and pumpkin pie spice until well-mixed and thick. (Start with 1 1/2 cups milk and beat until it's the consistency of a pudding—if it's too thick, continue to add the rest of the milk.)
Step 3: Spread a thin layer of cream cheese mixture in a high-sided 9"-x-13" baking dish. Top with a layer of graham crackers. Add half the pudding mixture and top with a layer of half the cream cheese mixture. Drizzle with caramel and repeat, ending with the cream cheese layer (hold the caramel until ready to serve).
Step 4: Cover loosely with plastic wrap and refrigerate at least 6 hours and up to overnight.
Step 5: Drizzle with caramel and garnish with pecans before serving.
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