Pat the oxtails dry with paper towels, season with salt and pepper, and dust the pieces all over with flour. In a Dutch oven set over medium-high heat, add 2 tablespoons of oil. When the oil is hot, add the oxtails, working in batches as needed to avoid crowding. Let cook, turning occasionally, until deeply seared on all sides, 15–18 minutes total.

Transfer the meat to a large platter; drain and discard any excess fat from the pan (do not wash the pan). Return the pan to the stove and add the remaining 2 tablespoons of oil. When the oil is hot, add the onion, celery, and carrots, and cook, stirring occasionally, until the vegetables are soft but not yet colored, 4–5 minutes. Add the garlic, brown sugar, jerk seasoning, ginger, bay leaf, anise, cloves, and wine and stir, scraping the bottom of the pot with a wooden spoon to deglaze. Bring to a simmer and cook until the wine has reduced slightly, 5–7 minutes. Add the stock, bring to a simmer, cover, and cook, skimming the grease and gently stirring occasionally, until the meat is very tender, 8–9 hours. Adjust the seasoning with salt and pepper to taste.

Combine durum wheat flour and semolina flour in a large bowl. Bring a small saucepan of water to a bare simmer. Add ⅔ cup hot water to flours and mix with a fork until mixture just comes together. Turn out dough onto a surface lightly dusted with durum wheat flour and knead until smooth and elastic, 8–10 minutes (alternatively, using a stand mixer fitted with a dough hook, mix on low speed, about 5 minutes). Wrap tightly in plastic wrap; let sit 1 hour at room temperature.

Do Ahead: Pasta dough can be made 1 day ahead. Wrap tightly and chill.

Remove meat from Dutch oven to a platter and allow to cool. Remove bay leaf and star anise from broth and discard.

Strain remaining vegetables from broth then finely chop vegetables. After the oxtail has cooled enough to handle de-bone and finely shred the meat. Combine shredded meat with vegetable mixture.

Roll the pasta out into strips using the machine. Thickness 5 is a good choice for most machines. You want the pasta thin enough to form around the filling but not so thin that it tears easily.

Use your ravioli cutter to determine how far apart to place the mounds of filling. Depending on the size of the cutter you will use from 1 to 3 tablespoons or filling per ravioli.

Carefully place the filling on a strip of the pasta dough then use a brush or your finger tips to lightly wet the bottom strip of dough around the mounds of filling.

Place another strip of dough on top of the filling and gently form around the filling, pressing all around to seal the two strips of dough together.

Cut the raviolis using the cutter and place the raviolis on waxed paper making sure they don’t touch each other. Set aside the scraps of dough to re-roll. Repeat this process until all of the dough or filling has been used.

I like to serve the raviolis in the hot broth but they can be served with other sauces.

If you have the time and want to make the broth into a consommé that is a delicious way to go as well.