Heat olive oil in a large pot or deep skillet over medium heat.
Add the Italian sausage, breaking it up with a spoon, and cook until browned and cooked through, about 5-7 minutes.
Add the diced onion and cook until softened, about 3 minutes.
Stir in the minced garlic and red pepper flakes and cook for 1 minute until fragrant.
Add the diced tomatoes, chicken broth, uncooked penne pasta, dried oregano, and dried basil. Stir well to combine.
Bring the mixture to a boil, then reduce heat to medium-low and simmer uncovered, stirring occasionally, until the pasta is tender and most of the liquid is absorbed, about 12-15 minutes.
Stir in the chopped kale and cook for an additional 3-4 minutes until the kale is wilted and tender.
Season with salt and freshly ground black pepper to taste.
Serve hot, topped with grated Parmesan cheese.