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1
Preheat oven to 350u00b0 F (or prepare slow cooker).
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2
In a large Dutch oven, heat the oil over medium-high heat. Season the roast liberally with salt and pepper. Add the roast to the pan and sear until golden brown, approximately 6-7 minutes. Turn the roast over and repeat searing until all sides are golden brown. Remove the roast from the pot and set aside.
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3
Add the celery and onions to the pot and cook until softened. Stir in the red pepper and garlic cooking for one minute. Stir in the tomato paste and cook until it becomes a deep burgundy color. Add the red wine and vinegar to the pan to deglaze scraping the bottom of the pan with a wooden spoon to remove the brown bits. Stir in the cinnamon.
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4
If you're using slow cooker, add the beef to the slow cooker at this point and pour the onion mixture over it. Add the bay leaves, thyme, rosemary and sage to the slow cooker. Add the beef stock. Cover and cook on high for 4 hours or low for 7-8 hours. When the roast has one hour left, add the squash and plums. Cook for one more hour and then transfer to the roast to a platter to slice. Serve with the squash, plums and sauce.
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5
If you're using the oven, add the roast back to the pan. Tie the herbs together with kitchen twine and add to the pot. Add the beef stock and cover. Transfer the pot to the oven and roast for 1 hour. Check the liquid level and add 1/2 cup of stock if needed (if the roast is less than half covered, add stock). Replace the lid and cook for another hour. Add the squash and plums (and more stock if needed). Cover and continue cooking for 30 minutes. Remove the lid and cook for 30 more minutes.
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6
Transfer the roast to a serving platter and allow to rest for 10 minutes before slicing and serving with the squash, plums, and sauce.
