Place Oxtails in a Mixing Bowl and season generously with Salt and Pepper. Using your hands, rub the seasoning into the meat.
Heat a skillet on medium/high drizzling Olive Oil to coat the bottom.
Add Oxtails in and begin searing on each side for 2-3 minutes to create a light crust to keep flavors in. Transfer into Crockpot.
Add Onions, Habanero, Garlic, Brown Sugar, Soy Sauce, Browning Sauce, Dry Red Wine, Bullion, Cornstarch, Fire Roasted Tomatoes, Garlic Herb Seasoning, Onion Powder, Garlic Powder, Cumin, Thyme and a couple of generous pinches of Salt and Pepper. Using your mixing spoon, give it a good mix to incorporate flavors into meat.
Fill Crockpot with water until it reaches right over the mixture giving it an additional stir.
Cover with lid and turn on Crockpot on low to cook for 6-8 hours stirring occasionally if you are around.
When there is 2 hours or so remaining, add the diced Sweet Potatoes, Okra and Carrots and give them a stir to incorporate into Oxtail mixture. Taste the sauce to see if additional seasoning needed. Continue cooking until the meat is tender and the vegetables are cooked through. Depending on how thick you want your stew, you can create a slurry of 1:1 ratio of cornstarch and water and add to stew to thicken more if desired.
Serve over white rice or enjoy on its own.