Heat 2 tablespoons of olive oil in a heavy pan. Add the onion and garlic and gently soften over a low heat for about 10 minutes, taking care not to brown. Add the anchovies, chilli and a pinch of salt and continue stirring while the anchovies melt (1-2 minutes).
Add the cuttlefish, tomato and wine. Half cover the pan and cook very gently until the cuttlefish is tender, about 4 minutes.
Share the cuttlefish across 4 plates, add a grind of pepper, season with salt, squeeze the lemon over the top, drizzle with olive oil, sprinkle with parsley and serve immediately.