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Preheat the oven to 425 degrees F.
In a large oven safe pot, combine the tomatoes, onion, olive oil, thyme, and a pinch each of salt and pepper.
Transfer to the oven and roast for 20-30 minutes or until the tomatoes just begin to char and release their juices. Let cool slightly.
Transfer the roasted tomatoes and their juices to a blender and add the milk. Puree until smooth.
Return the soup to the pot and place over medium heat on the stove.
Stir in the pesto and season the soup with salt and pepper.
Thin with more milk if desired.
To serve, ladle the soup among bowls and top with parmesan and basil. Serve with a grilled cheese on the side.