Prepare the Beef

1. Preheat the Oven: Preheat your oven to 325°F (165°C).
2. Season the Beef: Season the beef chuck roast generously with salt and pepper.
3. Brown the Beef: Heat olive oil in a large Dutch oven or oven-safe pot over medium-high heat. Add the beef and brown it on all sides, about 5-7 minutes. Remove the beef and set it aside.
4. Sauté the Onion and Garlic: In the same pot, add the chopped onion and garlic. Sauté for 3-4 minutes, until the onion becomes soft and fragrant.

Create the Braising Liquid

1. Deglaze the Pot: Pour in the red wine, scraping the bottom of the pot to loosen any browned bits. Let it simmer for a minute to reduce slightly.
2. Add the Broth and Seasonings: Stir in the beef broth, tomato paste, Worcestershire sauce, bay leaf, and thyme.
3. Return the Beef: Place the browned beef back into the pot, ensuring it’s partially submerged in the liquid.

Braised Cooking

1. Cover and Cook: Cover the pot with a lid and transfer it to the preheated oven. Braise the beef for 2 to 2 ½ hours, or until the beef is fork-tender and easily pulls apart.
2. Add Cranberries: About 30 minutes before the beef is done, stir in the fresh cranberries, brown sugar, and balsamic vinegar. Cover and continue braising.

Finish the Dish

1. Remove the Beef: Once the beef is tender, remove it from the pot and place it on a cutting board. Let it rest for a few minutes before slicing or shredding.
2. Reduce the Sauce: Simmer the braising liquid on the stovetop for 10-15 minutes to thicken the sauce if needed.
3. Serve: Slice or shred the beef and serve it with the cranberry sauce poured over the top.