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1. Preheat oven to 425°.
2. Halve half of tomatoes. Arrange cut tomatoes, whole tomatoes, and shallots on a jelly-roll pan coated with cooking spray. Drizzle with 1 tablespoon oil; toss. Bake at 425° for 35 minutes.
3. Add 2 tablespoons oil, vinegar, salt, and pepper to pan. Bake 10 minutes.
4. Cook ravioli according to package directions, omitting salt and fat. Drain ravioli, reserving 1/4 cup cooking liquid. Add ravioli to tomatoes; toss. Add cooking liquid, if needed. Garnish with chopped basil.
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