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Salt the chuck roast a day before if possible, or at least one hour prior to cooking. (1 tsp Kosher salt per lb meat)
Pat chuck roast dry. Add oil to pot, heated to just shy of smoking. Sear on all sides until deeply browned and crusty. Remove and set aside.
Lower heat, saute onions a few minutes until edges brown. Stir in paprika, black pepper, chili flakes, tomato paste. Cook 1 minute.
Pour in balsamic vinegar, coffee, 2 cups stock. Scrape up browned bits in the pot. Add dates, garlic, coconut aminos, vanilla, bay leaves, orange peel. Bring liquid up to a boil.
Return chuck roast to pot. Braising liquid should come at least ¾ of the way to the top, but not submerge. Add additional stock or water if needed.
Cover pot, leaving lid slightly ajar. Transfer to oven and cook at 275°F for 3-4 hours. The size of roast will determine total cooking time. Flip halfway through cook time. (Internal temp should finish at 200-210F; meat should be fork tender but hold together enough to slice.)
Remove pot roast. Strain sauce, reserve the roasted garlic.Return sauce to pot, skim the fat. Mash the roasted garlic cloves into the sauce. Simmer the sauce to reduce to desired consistency. Slice pot roast and return to pot.