For the fried shallots

1. Prep shallots. In a small bowl, toss the shallot rings in the flour until coated.
2. Fry shallots. In a 10-inch skillet, heat 3 tablespoons of the olive oil over medium-high heat until shimmering. Add about half the shallot rings to the hot oil and fry until golden brown, adding more oil if necessary, 3 to 4 minutes. Stir the shallots occasionally to promote even browning. Using tongs, transfer the fried shallots to a paper-towel-lined plate and sprinkle lightly with salt. Repeat with remaining shallots. Set aside.

For the pasta

1. Cook pasta. Bring a large pot of lightly salted water to a boil and add the penne pasta. Cook the penne until just al dente, about 10 minutes, stirring occasionally.
2. Prep shrimp. While the pasta is cooking, prepare the sauce ingredients. Pat the shrimp dry with paper towel. Toss the shrimp with 1/2 teaspoon kosher salt and 1/2 teaspoon pepper until evenly coated. Set aside.
3. Prep tomatoes and garlic. Slice the sun-dried tomatoes into julienne strips and thinly slice the garlic. Set aside.
4. Drain pasta. When the pasta is done cooking, drain the pasta. Set aside.
5. Cook shrimp. Wipe out the cooking pan and add 2 tablespoons olive oil and the butter. Heat the oil and butter over medium-high heat. When the butter is melted, add half of the shrimp and cook until just cooked through, about 30 seconds per side. Transfer to a plate and repeat with the remaining shrimp.
6. Cook aromatics. Add 2 tablespoons of oil, garlic, and shallot strips to the pan and cook, stirring, until golden brown in spots, 2 to 3 minutes.
7. Add wine. Add the Madeira and cook until almost fully evaporated, about 3 minutes, scraping up any browned bits from the bottom of the pan with a spatula.
8. Finish sauce. Add the tomatoes and cook another minute. Stir in the clam juice and cream; cook until the sauce thickens, 4 to 5 minutes.
9. Toss. Add the shrimp and cook until just heated through. Season to taste with salt and pepper. Add the pasta to the sauce and toss until the sauce evenly coats the pasta.
10. Serve. Divide the pasta among four shallow bowls, garnish with the parsley and fried shallots, and serve immediately.