Season meat generously with salt and pepper. Heat a heavy bottom pot or braiser on high. Once the pan is hot, add oil. Add the meat and sear 3 minutes per side or until brown. Remove meat set aside.
Add additional oil if needed. Add shallots, garlic, thyme, and rosemary. Sauté for 2 minutes. Add wine, water, and brown sugar. Let boil for 2 minutes then return meat to pot. Season liquid with 2 tsp salt. Cover pot and bake for 2 hours.
Prepare the potatoes. Raise oven temperature to 425°F. Place potatoes on a lined baking sheet, toss with oil, and season with salt and pepper. Place them cut side down. Bake for 25 minutes.
After the meat has cooked for 2 hours, add cooked potatoes to the pot. Make sure the meat is somewhat submerged in liquid and the potatoes are on top. Return pan to oven and cook uncovered for an additional hour, or until meat is fork tender (total cooking time is at least 3 hours, sometimes 3 ½ depending on your oven and the size of the beef).