Preheat your oven to 325°F (160°C). Pat the roast dry and season generously with kosher salt and black pepper.

Heat olive oil in a large Dutch oven over medium-high heat. Add the roast and brown for about 4–5 minutes per side until it has a deep, caramelized crust. Transfer the roast to a plate.

Lower heat to medium. Add onions, carrots, and celery to the pot. Cook until the onion softens, about 5 minutes. Add garlic and tomato paste; cook for 1–2 minutes until fragrant.

If using wine, pour it in now to deglaze the pan, scraping up browned bits.

Return the roast to the pot. Pour in beef broth until it comes about halfway up the roast. Add rosemary, thyme, and bay leaves. Bring to a simmer.

Cover the Dutch oven and transfer it to the oven. Braise for 3 to 3 1/2 hours, or until the roast is fork-tender.

Combine cranberries, brown sugar, balsamic vinegar, orange juice, Worcestershire, and a pinch of salt in a small saucepan. Bring to a simmer over medium heat and cook until cranberries burst, about 10–12 minutes.

If desired, stir in cornstarch slurry and simmer for another minute.

When the roast is ready, remove it from the oven and let it rest for 10–15 minutes. Spoon a little of the braising liquid over the roast and brush the cranberry balsamic glaze generously over it right before serving.

If desired, pop it under the broiler for 1–2 minutes for a caramelized finish.

Slice or shred the roast and serve with extra glaze and braising vegetables. Garnish with chopped parsley.