Make the tomato confit: Preheat oven to 300 degrees. Place the tomatoes in a deep pan or dutch oven. Nestle garlic, oregano, and rosemary around tomatoes. Add chile flakes, salt, and pepper and pour olive oil over everything, covering ingredients. Place pan in oven and cook for 45 minutes until tomatoes are soft and cooked through.Make the cavatelli: Combine squash, flour, cornstarch, eggs, and seasonings together in a large mixing bowl. Knead by hand until a smooth dough is formed. Let rest for 20 minutes.Lightly dust a work surface and a tray or sheet pan with semolina and turn dough onto surface. Use a rolling pinto gently flatten the dough into an even square, about ½-inch thick. Use a paring knife to cut dough into ½-inch thin strips and dust the strips with flour. Cut each strip into ½-inch pieces, or pillows, and dust with more flour. Roll each pasta pillow against the tines of a fork to create lines on each piece of cavatelli. Place finished cavatelli on the prepared tray or sheet pan.Fill a large pot with salted water and bring to a boil. Carefully add cavatelli and cook for 4 to 5 minutes until all pieces float to the top of the water.Meanwhile, transfer tomato confit to a large sauté pan and place over medium heat. Use a slotted spoon to transfer cooked cavatelli to the tomato confit. Add ½ cup of pasta cooking liquid and continue to cook over medium heat until the sauce is reduced slightly, about 5 to 7 minutes. To serve, plate the pasta and sauce in a large serving dish and garnish with grated pecorino.