Preheat the oven to 375 degrees Fahrenheit. For the filling, mix together the squash, 1 cup sugar, cinnamon, and vanilla extract in a medium bowl until smooth. Set aside.

Lightly grease a round baking pan or Dutch oven that’s roughly 10 to 12 inches in diameter and set it aside. When you’ve opened the air-tight package of the filo, lay it flat on a clean working surface and cover it with a clean kitchen towel. Each time you grab a sheet of filo from the pile, make sure to cover the pile with the kitchen towel, otherwise it will dry out very quickly, crumble around the edges, and become impossible to work with.

On a clean flat working surface, lay out one sheet of the filo dough and lightly brush it with olive oil, brushing all the day to the edges. Lay another sheet on top of it, and lightly brush it with olive oil as well. Repeat 4 more times, so you have 6 sheets of filo dough on top of each other. Take a large spoonful of the filling and empty it about 1-inch from the edge of one of the long sides of the filo in a straight line that’s about 1-inch wide and begins and ends about 1-inch from the edge of the dough, refilling the spoon with the filling as necessary to make the complete line. Take the edge of the filo closest to the filling line and roll it over the filling, taking care to keep the filling inside. Keep rolling it until all the filo is rolled up and you have a long cylinder of stuffing. Place the cylinder in the pan, bending it as necessary to shape it to the circular edge of the pan. Brush the placed cylinder with olive oil.

Repeat this process again so you have another cylinder of stuffing wrapped in filo, and line up the end of this cylinder with the end of the last one, forming a spiral shape in the pan. Brush the placed cylinder with olive oil. Repeat until you have filled up the pan with the stuffed filo cylinders and created a spiral, which will take about 4 to 6 stuffed cylinders total.

Sprinkle the remaining 2 tablespoons of sugar over the pan. Place the pan in the oven and bake until the filo turns golden and smells very aromatic, about 35 to 45 minutes. Remove from the oven and allow to cool for 20 minutes before slicing and serving.