1. Heat the olive oil in a large pot over medium heat. Add the Italian sausage, breaking it up with a wooden spoon as it cooks. Cook for about 6-8 minutes until browned and cooked through. Drain excess fat if necessary.
2. Add the chopped onion to the pot and sauté for 3-4 minutes until softened and translucent. Stir in the minced garlic and cook for another 1 minute until fragrant.
3. Pour in the chicken broth and diced tomatoes with their juice. Stir in the dried oregano and red pepper flakes, if using. Bring the soup to a gentle boil, then reduce the heat and simmer for 10 minutes to allow the flavors to meld.
4. Add the chopped kale to the pot and simmer for 5 minutes, or until the kale is tender but still vibrant green.
5. Gently stir in the ravioli and cook according to package instructions, usually about 3-5 minutes. Keep an eye on the ravioli to ensure they don’t overcook and fall apart.
6. Season the soup with salt and freshly ground black pepper to taste. If you like, sprinkle freshly grated Parmesan cheese on top before serving for an extra layer of richness.

One little trick I’ve learned is to always taste and adjust the seasoning at the end. Sometimes the sausage brings enough saltiness, but occasionally I need to add a pinch more. Also, be gentle when stirring the ravioli in—they’re delicate and shouldn’t be rushed or stirred too vigorously.