Preheat the oven: Set your oven to 300°F (150°C).
Make the dressing: In a small bowl, mix together 3 tablespoons olive oil, 2 tablespoons sugar, grated garlic, oregano, thyme, salt, and black pepper. Stir until combined.
Prep the tomatoes: Slice the cherry tomatoes in half and arrange them cut-side up on a baking sheet in a single layer.
Season the tomatoes: Spoon a little of the dressing over each tomato half. Try to coat as evenly as possible without drenching them.
Roast low and slow: Place in the oven and roast for 1½ hours. The tomatoes should be soft, shriveled, and slightly caramelized.
Baste and serve: Just before serving, spoon the flavorful oil and juices from the tray back over the tomatoes.
