Heat oil in a large heavy skillet over medium heat. Add guanciale and sauté until crisp and golden, about 4 minutes. Add pepper flakes and black pepper; stir for 10 seconds. Add onion and garlic; cook, stirring often, until soft, about 8 minutes. Add tomatoes, reduce heat to low, and cook, stirring occasionally, until sauce thickens, 15-20 minutes.
Meanwhile, bring a large pot of water to a boil. Season with salt; add the pasta and cook, stirring occasionally, until 2 minutes before al dente. Drain, reserving 1 cup of pasta cooking water.
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