Place cream cheese and 1/2 cup sugar in a medium mixing bowl. Mix until smooth.
Add canned pumpkin, vanilla and pumpkin pie spice. Blend until well combined.
Lay tortillas out flat on a work surface.
Spoon about 1/4 cup pumpkin filling in the center of each tortilla. Spread around covering tortilla close to the edges.
Roll each up carefully. Secure with a toothpick.
Pour enough oil into a large skillet to reach a depth of about 1/2-inch.
Place over medium heat and heat oil to 350°F.
Carefully drop 2 or 3 empanadas in oil. Fry til golden brown, turning as needed.
Remove to a paper towel-covered plate to drain.
Repeat until all empanadas are fried.
Remove toothpicks.
Pour 1/2 cup sugar and cinnamon into a shallow dish. Stir to mix well.
Then roll each empanada in mixture, turning to coat.
Serve hot, with a side of whipped cream, Cool Whip or whipped topping for dipping.