Preheat the oven to 300. Heat a Dutch Oven or large skillet over medium heat. Season the meat liberally with salt and pepper on all sides. Sear on all sides until evenly brown, about 5-10 minutes per side.
While the meat sears, prep the veggies. Mince the garlic. Peel the carrots and cut into large chunks. Dice the celery. Small dice one of the onions. Cut the other onion into large (about 8) chunks. Tie the stemmed herbs with food-safe twine.
Once seared, remove the meat from the dutch oven or skillet. Add in the diced onion (reserving the large chunks for later), garlic, and tomato paste, and saute until fragrant, about 5 minutes.
If using a Dutch Oven: add the wine directly into the dutch oven and use a spatula to scrape up any bits of onion stuck to the bottom. Then add the meat back in, along with the bundle of herbs, celery, carrots, and large chunks of onion. Top with beef stock as needed until about 3/4 of the meat is covered with liquid. Cover and place in the oven to cook until the meat is super tender, about 4 hours.
If using a skillet and casserole dish: splash a little bit of wine into the skillet with the cooked onions and use a spatula to scrape up the bits of onion from the pan. Then place the meat, veggies and herb bundle in the casserole dish. Add in the onions with cooked wine, followed by the rest of the wine and beef stock as needed until the meat is about 3/4 coved. Cover tightly with a lid or foil and bake until the meat is super tender, about 4 hours.