Combine flour, sugar, and salt in a large mixing bowl and make a well in the center.

Add the eggs, egg yolk, softened butter, grappa, and vanilla extract into the well.

Mix with a fork until the dough starts to come together, then turn it out onto a lightly floured surface.

Knead for 8-10 minutes until the dough is smooth, firm, and no longer sticky. It should feel like firm pasta dough.

Wrap the dough tightly in plastic wrap and rest at room temperature for 30 minutes. This step is not optional - resting relaxes the gluten so rolling is manageable.

Divide the rested dough into 4 portions. Keep unused portions wrapped while you work.

Using a pasta machine, pass each portion through progressively thinner settings from 1 down to 5 or 6, dusting lightly with flour as needed. If rolling by hand, roll to approximately 1 mm thickness - you should almost see your hand through the sheet.

Using a pastry wheel (fluted or straight) or a sharp knife, cut the sheets into rectangles roughly 10 cm x 5 cm (4 x 2 inches).

Cut a 3 cm slit lengthwise down the center of each rectangle. This is traditional and helps them puff and blister evenly.

Lay the cut pieces on a lightly floured tray in a single layer while you heat the oil.

Pour oil into a deep heavy saucepan to a depth of at least 6 cm. Heat over medium-high to 175-180 C / 347-356 F. Check with a thermometer.

Working in batches of 2-3, lower chiacchiere gently into the oil using tongs or a skimmer.

Fry for 45-60 seconds per side, turning once with tongs, until pale golden with visible bubbles and blisters on the surface. They color quickly so watch them.

Lift out with a slotted spoon or spider and transfer to a wire rack. Let the oil return to temperature between batches before adding the next.

Allow all fried chiacchiere to cool completely on the rack, about 10-15 minutes.

Once cool, transfer to a serving platter in a loose pile.

Sift powdered sugar generously over the top just before serving. Add a second layer of sugar if they look pale - they should look well snowed on.