Boil the pasta water. Fill a large stockpot about half full of water (roughly 3 quarts), add 2 tablespoons fine sea salt, and bring the water to a rapid boil.

Cut the guanciale. Slice the guanciale into ¼-inch-thick slices. Then cut each slice into roughly ½ x 1-inch pieces. (Tip: Freeze guanciale for 10 mins to make cutting easier).

Cook the guanciale. Heat a large sauté pan over medium-low heat. Add guanciale and cook, stirring, until golden brown and crispy, about 10 mins. Transfer guanciale to a plate. Save ¼ cup of the rendered fat; discard the rest.

Start the sauce. Add white wine to the saucepan, scraping up browned bits. Roughly crush drained tomatoes, add to pan with red pepper flakes, cooked guanciale, and reserved fat. Simmer gently while pasta cooks, adding pasta water if dry.

Cook the pasta. Add pasta to boiling water. Cook until about 2 minutes shy of al dente (still has a slight crunch).

Emulsify. Transfer pasta directly to the sauce using a spider strainer or tongs. Save remaining pasta water. Toss pasta continuously in sauce for 2-3 mins, adding pasta water as needed to create a glossy, emulsified sauce.

Finish & serve. Turn off heat. Gradually add grated Pecorino Romano, tossing until melted and sauce is glossy. Add more pasta water if needed to reach desired consistency. Serve immediately, garnished with extra cheese and black pepper.