Preheat your oven to 325°F. While the oven heats, pat the beef chuck roast completely dry with paper towels, then season it generously on all sides with the kosher salt and black pepper.
Heat the olive oil in a large, heavy-bottomed Dutch oven over medium-high heat. Carefully place the seasoned roast in the hot oil and sear for 4-5 minutes per side, until a dark brown crust forms on all surfaces.
While the meat sears, prepare the cranberry balsamic glaze by whisking together the fresh cranberries, balsamic vinegar, packed brown sugar, beef broth, and minced garlic in a medium bowl.
Once the roast is seared, carefully pour the prepared glaze over and around the meat in the Dutch oven, then add the fresh rosemary sprig.
Cover the Dutch oven with its lid and transfer it to the preheated oven. Roast for 2 1/2 to 3 hours, or until the meat is extremely tender and easily pulls apart when pierced with a fork.
Carefully remove the roast from the oven and transfer the meat to a cutting board. Let it rest for 10-15 minutes before slicing or shredding against the grain. While the meat rests, use a spoon to skim any excess fat from the surface of the cooking liquid in the pot.
For a thicker sauce, simmer the liquid on the stovetop over medium heat for 5-7 minutes until it reduces slightly.
Serve the sliced or shredded roast beef drizzled generously with the reduced cranberry balsamic pan sauce.