Heat the oil in a medium (5-quart) dutch oven or heavy-bottomed soup pot over medium-high heat. Sear the oxtails in two batches, taking care not to crowd the pan, browning them on all sides. Transfer browned oxtails to a plate and set aside.

Add the onions, carrots, and salt to the dutch oven and turn the heat down to medium. Cover the pot, allowing the vegetables to sweat until the onions are softened and translucent, about 10 minutes.

Uncover the pot, then stir in the Jerk Seasoning and Habanero Garlic Pepper, sautéing until aromatic, about one minute. Add the tomatoes and sauté for another two minutes.

Add the oxtails back to the pot, then pour in the red wine and beef broth. Stir to combine, bring up to a simmer, then turn heat down to low. Cover and let simmer until oxtails are very tender but not falling apart, about three and a half to four hours.

If you are making the stew in advance, chill it in the refrigerator until solid, then skim off the layer of fat on top. Rewarm the stew over low heat, then serve over mashed potatoes, rice, or noodles.