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Heat a large skillet over medium heat. Add the olive oil, then add the crumbled or sliced Italian sausage. Cook until browned and fully cooked, about 5-7 minutes. Remove the sausage from the pan and set aside.
In the same pan, add the minced garlic and red pepper flakes. Sauté for about 30 seconds until fragrant, being careful not to burn the garlic.
Add the cherry tomatoes to the skillet and cook for 4-5 minutes until they begin to blister and burst, releasing their natural sweetness into the dish.
Stir in the dried oregano, dried basil, and orzo pasta. Toast the orzo for about 1-2 minutes to enhance its nutty flavor.
Pour in the chicken broth, scraping up any browned bits from the bottom of the pan. Bring to a gentle simmer and cook for about 10 minutes, stirring occasionally, until the orzo is tender and has absorbed most of the broth.
Stir in the spinach or kale, allowing it to wilt into the dish. Return the cooked sausage to the pan and mix everything together.
Sprinkle in the grated Parmesan cheese and stir until melted and creamy. Taste and adjust seasoning with salt and freshly ground black pepper.
Dish out the orzo into bowls and serve warm. Garnish with extra Parmesan and a drizzle of olive oil if desired.