Line one tray and one baking sheet with parchment paper.

Beat cream cheese, powdered sugar, and 1/2 teaspoon vanilla with an electric mixer until thoroughly combined.

Scoop cream cheese mixture onto the prepared tray into 18 mounds. Freeze until solid, about 1 hour.

Preheat the oven to 375°F (190°C). Spread canned pumpkin on a plate and blot with paper towels to remove moisture.

Mix together flour, 2 teaspoons pumpkin pie spice, baking soda, and salt.

Beat butter on medium speed for 30 seconds. Add brown sugar and 1/4 cup white sugar, then beat until combined.

Add canned pumpkin and remaining 1 teaspoon vanilla, then beat until combined. Stir in the flour mixture with a wooden spoon.

Combine remaining 1/4 cup white sugar and 1 teaspoon pumpkin pie spice in a small bowl.

Portion cookie dough into 18 pieces. Flatten a piece, place a frozen cream cheese mound in the center, and wrap the dough around it to form a ball.

Roll the cookie ball in the sugar mixture, then place on the baking sheet. Repeat with all dough.