Cook the Pasta: Bring a large pot of well-salted water to a boil. Add the penne and cook until al dente according to the package directions. Drain the pasta well.
12 ounces penne pasta
Make the Parmesan Vinaigrette: While the pasta cooks, add the olive oil, grated garlic, red wine vinegar, lemon juice, Dijon mustard, dried oregano, salt, black pepper, and ½ cup Parmesan cheese to a large mixing bowl. Whisk until combined.
6 tablespoons extra-virgin olive oil, 2 garlic cloves, 3 tablespoons red wine vinegar, 3 tablespoons fresh lemon juice, 1 teaspoon Dijon mustard, 1 teaspoon dried oregano, ½ teaspoon kosher salt, ¼ teaspoon freshly ground black pepper, ½ cup freshly grated Parmesan cheese
Toss the Hot Pasta: Add the hot drained pasta directly to the Parmesan vinaigrette. Toss well with tongs so the pasta absorbs the dressing and the heat softens the sharp bite of the raw garlic.
Start the Sausage: Preheat a gas grill or grill pan to medium-low heat, about 250°F to 325°F, and lightly grease the grates. Add the chicken sausages and cook for 8 to 10 minutes, turning every few minutes, until they reach about 145°F.
4 mild Italian chicken sausages
Season the Vegetables: While the sausage starts cooking, brush the red bell pepper pieces and red onion slices with 1 tablespoon olive oil. Sprinkle them with ½ teaspoon kosher salt.
1 tablespoon extra-virgin olive oil, 1 large red bell pepper, 1 medium red onion, ½ teaspoon kosher salt
Grill the Vegetables: Turn the grill up to medium-high heat and add the peppers and onions beside the sausage. Grill the sausage until lightly charred and cooked through to 165°F, then remove it from the grill and let it rest.
Finish the Peppers and Onions: Keep grilling the vegetables until they are tender and charred in spots, about 8 to 10 minutes total, flipping halfway through. Let them cool slightly.
Slice the Sausage: Transfer the grilled chicken sausage to a cutting board and slice it diagonally into ¼-inch pieces. Add the sliced sausage to the pasta bowl.
Chop the Vegetables: Chop the grilled red pepper and onion into medium-size pieces. Add them to the pasta and toss everything together.
Finish the Pasta Salad: Add the olives, pepper drops or peppadews if using, parsley, baby arugula, and the remaining ¼ cup Parmesan cheese. Toss gently until everything is evenly coated.
½ cup pitted Castelvetrano olives, ¼ cup sweet and tangy pepper drops or peppadews, ¼ cup freshly grated Parmesan cheese, ¼ cup Italian parsley, 2 large handfuls baby arugula
Serve: Transfer the pasta salad to a serving platter and serve right away. You can also let it sit for a few minutes so the pasta, sausage, peppers, and Parmesan vinaigrette get properly acquainted.