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Step 1
Heat the olive oil in a large sauté pan over medium-high heat. Add the onion, garlic, rosemary, and thyme and cook about 4 minutes or until the onions are tender.
Step 2
Place the flour, salt, and pepper in a large bowl. Add the beef cubes and toss gently to coat. Add the beef to the pan and cook, turning occasionally, until the beef is browned on all sides and golden around the edges, about 5 minutes. Add the Marsala and use a wooden spoon or spatula to scrape up the browned bits from the bottom of the pan.
Step 3
Transfer the beef and pan juices to the slow cooker. Add the squash, sun-dried tomatoes, and broth and stir to combine. Cover and cook on high for 4 to 5 hours or on low for 8 hours until the beef and squash are tender. Serve with crusty bread and a sprinkle of parsley.