1. Preheat Your Oven and Prepare Baking Sheet:
* Preheat your oven to 400°F (200°C). A moderately high heat helps to caramelize the tomatoes effectively without them turning completely to mush.
* Line a large rimmed baking sheet with parchment paper for easy cleanup and to prevent sticking. If you don’t have parchment paper, you can lightly oil the baking sheet, but be aware tomatoes might stick a bit more.

2. Prepare the Roma Tomatoes:
* Wash the Roma tomatoes thoroughly under cool running water.
* Pat them completely dry with a clean kitchen towel or paper towels. Removing excess moisture helps them roast rather than steam.
* Slice the tomatoes in half lengthwise (from stem to end). If your Roma tomatoes are particularly large, you can quarter them lengthwise.
* If you prefer, you can core out the very top part where the stem was attached, though it’s not strictly necessary for Romas.

3. Season the Tomatoes:
* Place the halved or quartered Roma tomatoes in a large mixing bowl.
* Drizzle them with 3-4 tablespoons of extra virgin olive oil.
* Add the sliced or chopped garlic (if using whole cloves, just toss them in).
* Sprinkle with the dried Italian herbs (or your choice of dried herbs), coarse salt, and freshly ground black pepper. Add red pepper flakes or sugar at this stage if using.
* Gently toss everything together with your hands or a large spoon until the tomatoes are evenly coated with the oil and seasonings. Ensure the garlic is distributed amongst the tomatoes.

4. Arrange Tomatoes on the Baking Sheet:
* Carefully arrange the seasoned Roma tomatoes in a single layer on the prepared baking sheet.
* Place them cut-side up. This allows some of the moisture to evaporate and helps the cut surfaces to lightly caramelize.
* Ensure there is some space between the tomatoes. Overcrowding the pan will cause the tomatoes to steam rather than roast, and you won’t achieve that desirable caramelization. Use two baking sheets if necessary.
* If using fresh sprigs of thyme or rosemary, tuck them amongst the tomatoes on the baking sheet.

5. Roast the Tomatoes:
* Place the baking sheet in the preheated oven.
* Roast for 25-40 minutes. The exact roasting time will depend on the size of your tomatoes, their moisture content, and your oven’s specific performance.
* Check the tomatoes around the 25-minute mark. They are done when they are softened, slightly wrinkled, and have started to caramelize around the edges (showing some browned spots). The juices released should be syrupy.
* For more intense caramelization, you can roast them a bit longer, but watch carefully to prevent them from burning.

6. (Optional) Add Finishing Touches:
* If using balsamic vinegar or glaze, you can drizzle it over the tomatoes during the last 5-10 minutes of roasting or immediately after they come out of the oven.
* Once removed from the oven, if using fresh basil, tear or chiffonade the leaves and sprinkle them over the hot roasted tomatoes.

7. Cool and Serve/Store:
* Let the roasted Roma tomatoes cool on the baking sheet for a few minutes. They will be very hot.
* Serve warm or at room temperature.
* If not using immediately, allow them to cool completely before storing.