Start by cleaning the squid thoroughly under cool running water. Remove any remnants and pat dry.

In a skillet, heat 2 tablespoons of olive oil over medium heat. Sauté the chopped squid tentacles and garlic for about 5 minutes. Transfer to a food processor, add bread crumbs, Pecorino Romano cheese, parsley, capers, salt, and black pepper. Pulse until combined.

Carefully fill each squid tube with the prepared filling, leaving space at the top. Secure ends with toothpicks and prick the squid all over with a skewer.

In the same skillet, heat another tablespoon of olive oil and sauté minced garlic for 1 minute. Deglaze with white wine, then add canned tomatoes, black olives, and remaining seasoning. Simmer for 10 minutes.

Gently add the stuffed squid to the simmering sauce. Cover and simmer on low heat for 30 to 60 minutes, turning the squid occasionally.

Remove squid from the sauce, slice into rings, and serve with freshly cooked pasta, tossing in the sauce.