To make the ravioli: place the flours on a clean, flat surface. Place the eggs/olive oil in a well in the middle. Whisk eggs and slowly incorporate the flour using a fork and bench scrapper. Keep mixing, and once the dough starts to form, switch to your hands and knead the dough until the dough is smooth and no longer sticky (but not stiff). Add more flour as needed to reach this feeling. The dough should spring back when pressed. Form it into a disk, cover it with a damp towel, and let it rest for 20 minutes.
To make the filling: combine the squash with the mascarpone and salt, whipping together until as smooth as possible. Transfer to a piping bag or have a spoon ready.
Divide the dough into 4 pieces. Flatten the dough with your hands, working with one piece at a time and keeping the rest covered. Coat the pasta in a bit of flour, then use your chosen machine to roll the pasta into sheets until you reach the desired thickness–I use a Marcato Atlas to a 7.
I prefer smaller, 2" ravioli, which allows me to work with one sheet and fold over. I also like to mark where the filling will go with the back of a 1" biscuit cutter. Pipe or spoon the filling into each space, fold over the dough, press down again around the filling with the back of the biscuit cutter, then cut out each square (see the video will be helpful!)
To cook the ravioli: Once your ravioli is ready, boil a pot of salted water and place a few tablespoons of chile butter in a bowl. Add the ravioli to the pot and cook until tender, 2-3 minutes for fresh, 3-4 for frozen.
Using a spider strainer or slotted spoon, immediately transfer the ravioli to the bowl with the butter. Toss until the butter has melted and coated the ravioli.
Divide the ravioli into bowls and finish with fresh basil and a sprinkle of crushed crispy shallots.