Preheat your oven to 400°F. In a large oven-safe dish, add cherry tomatoes and halved garlic. Drizzle with olive oil and sprinkle Italian seasoning, red pepper flakes, salt, and black pepper. Toss to coat.
Roast in the oven for 35 minutes until tomatoes are soft and blistered.
While tomatoes roast, cook pasta in salted boiling water until al dente. Reserve 1/2 cup pasta water before draining.
Once tomatoes are roasted, mash them gently with a spoon. Stir in reserved pasta water and chopped basil.
Add cooked pasta to the tomato mixture and toss to combine until evenly coated.
Serve topped with fresh basil and pesto.
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Notes
Store leftovers in an airtight container in the fridge for up to 4 days. Reheat gently, adding a splash of water or olive oil if needed.