Preheat oven to 425 degrees.
On a parchment lined, rimmed baking sheet, add the cherry tomatoes, sliced shallots, crushed garlic and fresh oregano.
Drizzle with olive oil, sprinkle with red pepper flakes, sea salt and cracked pepper. Roast for 45 minutes.
Add the crushed tomatoes, white wine vinegar and lots of cracked pepper to a Dutch oven.
Add the roasted tomato mixture and all of the roasting juices. Stir to combine.
Bring to a boil over medium heat. Reduce heat to low and simmer for several hours. Stir occasionally, using the back of your spoon to crush the tomatoes and garlic cloves. The longer it simmers, the better it gets. Serve over your favorite pasta.