Pat the Beef Chuck dry and season generously with Sea Salt and Black Pepper. Heat a few tablespoons of Extra-Virgin Olive Oil in a large Dutch oven or heavy pot over medium‑high heat and brown the beef in batches until well caramelized on all sides; remove and set aside.
Reduce the heat to medium, add another splash of Extra-Virgin Olive Oil if needed and sauté the chopped Onion until soft and translucent, then add minced Garlic and cook for 30–60 seconds until fragrant.
Pour in the Dry Red Wine to deglaze the pan, scraping up all the browned bits; let the wine reduce by about half so the alcohol cooks off.
Return the browned Beef Chuck to the pot and add the Crushed Tomatoes, a couple of spoonfuls of Tomato Paste for body, and enough Beef Stock to just cover the meat. Tuck in a Bay Leaf and add a small stick or pinch of Cinnamon and a few Allspice Berries for that classic warm note.
Bring the mixture to a gentle simmer, cover partially, and braise on low heat (or place in a 160–170°C / 325°F oven) until the beef is very tender—about 1.5–2 hours depending on the cut.
When the beef is fork‑tender, remove it from the sauce and shred or cut into bite‑sized pieces; skim any excess fat from the sauce and taste, adjusting with a little more Sea Salt and Black Pepper if needed.
Stir the shredded beef back into the sauce, then add the Orzo (Kritharaki) directly to the pot, ensuring there is enough liquid for the pasta to absorb (add a bit more Beef Stock or water if needed). Transfer everything to an oven‑safe baking dish if your pot is not ovenproof.
Cover the dish and bake in a 180°C / 350°F oven for about 20–30 minutes, or until the orzo is tender and has absorbed most of the sauce; uncover for the last 5–10 minutes to let the top thicken slightly.
Remove from the oven, grate a generous amount of Kefalotyri over the top, and return to the oven briefly to melt and lightly brown the cheese. Let rest for 5 minutes before serving so the sauce sets slightly.
