Place the tomatoes on a baking sheet that has been lightly drizzled with olive oil. drizzle the tomatoes with olive oil and toss to coat.
sprinkle evenly with kosher salt and black pepper.
roast at 425 for 20-40 minutes or until shriveled and soft.
remove from the oven.
let cool for a few minutes and then place the tomatoes and any accumulated juices from the pan into a blender (we use blendtec) and puree until you have 2 1/2 cups. if you come up short just add tomato sauce or too much just don't use it all.
drizzle about 2 teaspoons of olive oil in a large sauce pot.
heat over medium high heat until shimmering.
add the garlic, turn down to medium and stir frequently.
allow to cook until fragrant, about 30 seconds.
add the tomato puree, juice, broth, tomato sauce brown sugar, salt and pepper.
stir and then allow to come to a boil.
boil for 10 minutes and turn down to a simmer.
add the milk and simmer for 10-15 minutes.
Stir in the butter and basil.
Meanwhile, cook the pasta per package instructions.
Ladle the soup into bowls, add a little pasta and parmesan and serve immediately.
Allow soup to cool and store in tupperware up to 4 days or in sealed storage bags in the freezer up to 2 months.