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Pat the chuck roast dry, add 2 tbsp olive oil (2 tsp each side) and season generously with steak seasoning.
Heat a large Dutch oven over medium-high heat with oil.
Sear the roast on all sides until deeply browned (3–4 minutes per side). Remove and set aside.
In the same pot, add onion, shallot, and celery.
Sauté 4–5 minutes until softened.
Stir in tomato paste and cook until darkened and caramelized (about 2 minutes).
Pour in the red wine, scraping up all the browned bits.
Simmer red wine to reduce about 50% (about 4-5 minutes).
Add beef stock, bouillon base, Worcestershire, pepperoncini juice, liquid smoke (if using), and brown sugar.
Stir in garlic powder, onion powder, oregano, smoked paprika, and MSG (if using).
Nestle the roast back into the pot.
Add bay leaves, herb sprigs, and the head of garlic.
Cover and transfer to a 350°F (165°C) oven. Braise for 3.5 - 4 hours, adding carrots and potatoes in the final hour.
Remove herb stems and bay leaves.
Taste and adjust salt and pepper.