In a large bowl, mix together potatoes, oil, garlic, rosemary, salt, and pepper. Spread out in a large baking pan and cover with foil. Cook for 20 minutes. Remove from oven and stir potatoes. Return to oven, uncovered, and roast for another 10 minutes or until golden brown.
Place roasted potatoes in a large pot with crushed tomatoes and broth. Use an immersion blender to puree soup (or put ingredients in a blender and then return to the pot.)
Slowly mix in the milk and heat the soup until warm. Ladle into bowls and sprinkle each with 1 tablespoon of Parmesan cheese.
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