Preheat oven to 300°, chop all vegetables and have ready all ingredients.
On the stove top, preheat a large soup pot or dutch oven over medium high heat and add oil. Season the roast generously on all sides with salt and pepper, then coat with flour. This forms a nice crust on the roast when you sear it and thickens the sauce as it cooks.
Add beef to the hot pot, letting it sear on one side to a dark brown color, do not move it around in the pot (about 6 to 7 minutes per side). When browned, flip the beef with tongs to brown the other side. While the second side is browning, add the vegetables (not the garlic yet) to start sautéing around the beef.
Add all other ingredients including garlic, except the wine and stock.
When the second side is browned and vegetables are cooking, deglaze with the wine and mix all ingredients so beef is not stuck to the pot. Add the beef stock and stir.
Cover and transfer the entire pot to the oven. Cook for 7 to 8 hours, stirring and flipping the roast once or twice throughout the day. REMOVE the cover for the final hour of cooking to allow the sauce to thicken and reduce.
After 8 hours the meat will be extremely tender and can be shredded with tongs (Note: Oven heat and roast size can vary, make sure to check on the roast in the last 1 or 2 hours. If it has a lot of liquid, remove the cover to allow it to thicken, if you are running out of liquid, either add water or turn the oven off). The liquid will have reduced leaving tender beef in a dark sauce. Serve the beef with tongs to leave the rendered fat in the pot.
Serve with potatoes or mashed cauliflower, over grilled bread, or on sandwich buns. Leftovers can be frozen.