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Bring a large pot of water to a boil. Add penne and cook according to package directions. Drain, return to the pot and cover to keep warm.
Meanwhile, heat oil in a large skillet over medium heat. Add onion and fennel and cook, stirring, until starting to soften, about 5 minutes. Add garlic, crushed red pepper, Italian seasoning, salt and pepper and cook for 1 minute more. Add tomatoes and their juice; bring to a simmer. Cook, stirring occasionally, for 10 minutes. Add shrimp and cook, stirring occasionally, until the shrimp is just cooked through, about 4 minutes.
Stir about 1/2 cup of the tomato sauce into the pasta to lightly coat it. Divide among 4 pasta bowls and top with the remaining shrimp and sauce. Serve sprinkled with chopped fennel fronds, if desired.