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Preheat the oven to 375°F (190°C). Bring a large pot of well-salted water to a boil. Add the jumbo shells and 1 tbsp olive oil and cook until just shy of al dente — tender but still with a firm bite at the center, about 9 minutes (they will finish cooking in the oven). Drain, rinse briefly under cold water to stop cooking, and spread on a lightly oiled baking sheet to prevent sticking.
While the shells cook, make the marinara. Heat 2 tbsp olive oil in a large skillet or saucepan over medium heat until shimmering. Add the garlic and red pepper flakes and cook, stirring frequently, until the garlic is fragrant and just beginning to turn golden at the edges, about 2 minutes — watch closely so it doesn't burn. Pour in the crushed tomatoes, add the sugar and salt, and stir to combine. Simmer over medium-low heat, stirring occasionally, until the sauce thickens slightly and the raw tomato smell mellows, about 15 minutes. Remove from heat.
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