Preheat oven to 300 degrees Fahrenheit. In a large cast iron skillet, layer the tomatoes in ⅓ cup good quality olive oil. Nestle the halve garlic head with the tomatoes, halved sides down. Season with a pinch of salt and black pepper. Add the crushed red pepper flakes and nestle in the fresh herb sprigs. Give the mixture a light toss to coat everything together in the oil and aromatics.

Roast the tomatoes low and slow for about an hour and half. The tomatoes will begin to fall apart and the garlic should be knife tender. Remove from the oven. Discard the herb sprigs. Carefully remove the garlic cloves from their skins. Using the back of a wooden spoon, give the confit a light mash and stir everything together to combine.

During the last 15 minutes of cooking, bring a large pot of salted water to boil. Add your pasta of choice. Cook the pasta until al dente. Reserve about ½ cup of pasta water once cooked and add to the tomato and garlic confit. Give the pasta a good stir. Adjust seasoning as needed and garnish with chopped fresh herbs like parsley, basil, or chives.