In a spacious mixing bowl, blend cream cheese, canned pumpkin, sugar, and pumpkin pie spice using a hand mixer until smooth and creamy.

Gently fold in whipped topping into the pumpkin cream cheese mixture until well combined.

Transfer the pumpkin mixture into a large Ziploc bag and refrigerate for at least 1 hour.

In a large frying pan, pour in enough oil to reach halfway up the sides and heat over medium heat.

Mix sugar and cinnamon in a shallow bowl for coating.

Cut a small corner off the Ziploc bag, lay a tortilla flat, and pipe the pumpkin mixture down the center.

Carefully roll the tortilla away from you and use a toothpick to secure if necessary.

Fry the rolled tortilla seam-side down until golden brown, about 2-3 minutes on each side.

Remove from oil and roll in the cinnamon-sugar mixture until well coated.

Slice each rollup diagonally into bite-sized pieces and serve warm.