Preheat oven to 350°F (or prepare slow cooker).

Heat olive oil in a large Dutch oven over medium-high heat.

Season the chuck roast liberally with kosher salt and fresh ground pepper.

Sear the roast on all sides until golden brown, approximately 6-7 minutes per side.

Remove the roast from the pot and set aside.

Add diced celery and vidalia onions to the pot and cook until softened.

Stir in crushed red pepper and minced garlic, cooking for one minute.

Stir in tomato paste and cook until it becomes a deep burgundy color.

Deglaze the pan with red wine and cider vinegar, scraping up the brown bits.

Stir in cinnamon.

If using slow cooker, add the beef to the slow cooker and pour the onion mixture over it.

Add bay leaves, thyme, and sage to the slow cooker.

Add 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 diced butternut squash and halved dried plums.

Cook for one more hour and then transfer the roast to a platter to slice.

Serve with the squash, plums, and sauce from the slow cooker.

If using the oven, add the roast back to the Dutch oven.

Tie the herbs together with kitchen twine and add to the pot.

Add 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).

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.

Transfer the roast to a serving platter and allow to rest for 10 minutes before slicing.

Serve with the squash, plums, and sauce from the Dutch oven.