1. Prepare the Pumpkin Mixture: In a medium bowl, combine the pumpkin puree, granulated sugar, pumpkin pie spice, and vanilla extract. Stir everything together until it’s well blended and smooth. This will be the delicious filling for your donuts.

2. Unroll the Crescent Dough: Carefully open the can of crescent rolls. Unroll the dough onto a clean, lightly floured surface. Do not separate the individual triangles; instead, press the seams together firmly to form one large rectangular sheet of dough. You want to create a solid base for your donuts.

3. Fill and Roll the Dough: Spread the pumpkin mixture evenly over the entire surface of the crescent roll dough, leaving a small border around the edges. Starting from one of the longer sides, carefully roll the dough tightly into a log. Pinch the seam closed to secure the filling inside.

4. Slice the Donuts: Using a sharp knife, slice the dough log into 1-inch thick rounds. This will give you approximately 8-10 donuts, depending on how thickly you slice them. Gently reshape any that lose their round form.

5. Heat the Oil for Frying: Pour about 2-3 inches of vegetable oil into a large, heavy-bottomed pot or Dutch oven. Heat the oil over medium heat until it reaches 350 F (175 C). If you don’t have a thermometer, you can test the oil by dropping a small piece of dough in; it should sizzle and float to the top immediately.

6. Fry the Donuts: Carefully place a few donut slices into the hot oil, making sure not to overcrowd the pot. Fry for 2-3 minutes per side, or until they are golden brown and cooked through. Use a slotted spoon or tongs to flip them gently.

7. Drain and Glaze: Once golden, remove the donuts from the oil and place them on a wire rack lined with paper towels to drain any excess oil. While they are still warm, prepare the glaze. In a small bowl, whisk together the powdered sugar, milk, and ground cinnamon until smooth.

8. Finish and Serve: Dip each warm donut into the glaze, coating both sides, or drizzle the glaze over them. Place them back on the wire rack to allow the glaze to set slightly. Serve these delicious homemade pumpkin donuts warm and enjoy!