Preheat the oven to 200C fan / 428F.
In an oven-proof tray add in baby tomatoes, shallots, and garlic bulb. Drizzle with olive oil, ground black pepper, salt, and dried oregano. Give everything a toss, then place in the oven for 30 minutes.
10 minutes before the tomatoes have finished cooking, get your pasta on and cook according to packet instructions in salted boiling water. Don't forget to save the pasta water.
Remove the tray from the oven and transfer 80% of the tomatoes (I like to set aside a few whole roasted baby tomatoes for texture but feel free to blend everything if you fancy) and all of the shallots into a food processor. Squeeze out the garlic cloves from the bulb into the processor. Blend until smooth.
Transfer the blended roasted tomato pasta sauce into a skillet and add in chili flakes, balsamic vinegar, sugar, salt, and pepper.
Add in your cooked pasta, the rest of your whole roasted baby tomatoes, and sliced basil with 50ml pasta water. Toss to combine on low heat.
Taste and season according to your preferences. Once ready, divide between your bowls and top with grated parmesan. Enjoy!