Pre-heat oven to 275 degrees. Season oxtails with salt and pepper. Dust oxtails with flour. Set aside
Heat olive oil in a large dutch oven pot on medium. Add the oxtails and brown on all sides. Be careful not to overcrowd the pan. If necessary brown in batches. Remove oxtails to a paper towel laden plate.
Take the habanero and using the sharp end of a knife puncture each side of the chili creating small slits/incisions.
Saute the onions, garlic, carrots, and celery for 4-5 minutes. Stir as needed.
Add the habanero and red bell peppers, mixing them in well with the other vegetables. Add the bay leaves, half the salt, pepper, and all spice seasonings. Let cook 2-3 minutes, mixing as needed.
Add the wine to the pot and deglaze using a wooden spoon to scrape up the bits.
Add the bbq sauce, beef broth and remaining spices. Mix well, then add the oxtails and fresh thyme.
Cover with heavy lid and bake for 4 hours. Oxtails should be fork tender. Sauce should have the consistency of a thin bbq sauce.