Preheat your oven to 375 degrees F and line two baking sheets with parchment paper or silicone baking mats.
Using an electric mixer, mix together the softened cream cheese, brown sugar, pumpkin puree, pumpkin pie spice, and vanilla extract, then set aside.
Open, unroll, and separate the dough from both cans of crescent rolls. Spoon about 1 tbsp of pumpkin filling onto the middle of the widest part of the dough, then smear it towards the tip, leaving a border around the edges.
Roll up each triangle, starting at the side opposite the point, and place each roll onto the lined baking sheets, leaving a little space between each one.
Combine the granulated sugar and remaining pumpkin pie spice in a shallow bowl.
Roll each rollup in the pumpkin spice sugar mixture to coat, then bake for 14-17 minutes or until puffy and golden brown.