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1
Preheat oven to 250u00b0F. Pour half of the extra virgin olive oil into a large glass or ceramic baking dish. Place tomatoes in dish cut side up.
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2
Pour remaining oil over tomatoes. Season with salt and pepper and sprinkle with sugar. Bake 1 hour. Using tongs, turn tomatoes over. Bake 1 hour longer. Turn tomatoes over again. Bake until deep red and very tender, 15-45 minutes longer, depending on ripeness of tomatoes.
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3
Transfer tomatoes and 1/4 cup of the oil to a large bowl, reserving the remaining oil for another use. Sprinkle garlic and parsley over tomatoes and let steep until tomatoes are room temperature. (Can be done and refrigerated up to five days ahead. Bring up to room temperature before using.)
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4
While the tomatoes are resting at room temperature, place yellow and green squash slices in a large mixing bowl. Add canola oil, salt, and freshly ground black pepper, and toss to coat.
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5
Heat a large saute or grill pan over medium heat until hot but not smoking. Working in batches, arrange squash slices in pan in a single layer and cook for two minutes on each side or until well-browned. Remove and transfer to the bowl containing the tomatoes, coating the slices in oil. Repeat with remaining squash.
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6
Bring a large pot of salted water to the boil and cook pasta until al dente. Drain and immediately toss with tomato, squash and olive oil mixture. If it seems a little dry, add some of the reserved oil until pasta is uniformly glossy. Serve hot or cooled to room temperature.
