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Heat an oven safe cast iron pan over medium heat. Add olive oil. Once oil is hot, add the sausage meat, using the back of a spatula to break the meat into small pieces,and cook until the meat is no longer pink in colour. Use a spatula to form a well in the center of the meat, add garlic and onions. Cook until fragrant and onions are translucent in colour (about 3 minutes).
Add butternut squash, tomatoes, sage, thyme and red pepper flakes. Stir.
Reduce heat to low, add chicken broth and bring to a low boil.
Once boiling, add orzo, stir and cover. Allow orzo to simmer until fully cooked (about 10 minutes). You may need to stir periodically, scraping the bottom of the pan to ensure the orzo does not stick.
Stir in kale, 1 cup at a time until it wilts. Top with feta cheese. To melt the cheese, broil at 500F for about 5 minutes.