Think melt-in-your-mouth pot roast: seared chuck, slow-braised in red wine and stock with plenty of aromatics. Squash goes in later so it stays tender; dried plums add gentle sweetness. Finish with a quick reduction (or slurry) for rich gravy, perfect on mashed potatoes or egg noodles.
Preheat oven to 350 degrees (or prepare slow cooker)
In a large dutch oven, heat the oil over med-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.
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.
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.
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.
Transfer the roast to a serving platter and allow to rest for 10 minutes before slicing and serving with the squash, plums and sauce.
Slow Cooker Instructions
For the 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.
Notes
Cut: Chuck roast = best tenderness. Pat dry and season generously for deeper browning.
Liquid ratio: About 1 cup wine + 2 cups stock; liquid should come ½–⅔ up the roast.
No wine? Use beef stock and 1 tablespoon balsamic vinegar (or 2 tsp red wine vinegar).
Herbs: Thyme or rosemary (use a little less rosemary; it’s stronger).
Vegetable timing: Add butternut squash for final 45–60 min; add dried plums for final 20–30 min.
Doneness cue: Roast is ready when a fork twists with little resistance (optional internal 205–210°F).
Thicken sauce: Reduce 10–15 min or whisk 1 Tbsp cornstarch + 1 Tbsp cold water per cup of juices; simmer 2–3 min.
Slow cooker: LOW 8–9 hrs (best) or HIGH 4–5 hrs; add squash last 1½–2 hrs (LOW)/1 hr (HIGH) and plums last 30–40 min.
Storage: Refrigerate 3–4 days in gravy; freeze up to 3 months. Reheat covered at 300–325°F with a splash of stock.
Equipment: 5–7 qt Dutch oven with tight-fitting lid.