In a large pot, heat 2 tablespoons of olive oil over medium-high heat. Add the beef chuck in batches, searing chunks until well-browned on all sides, about 5-7 minutes per batch.

In the same pot, add another tablespoon of olive oil if needed, then toss in sliced onions and minced garlic. Sauté for about 5 minutes until the onions are soft and translucent.

Pour in 1 cup of red wine, using a wooden spoon to scrape up the flavorful bits stuck to the bottom. Bring the mixture to a simmer for 3-4 minutes.

Stir in crushed tomatoes, a cinnamon stick, bay leaves, and dried oregano. Mix well and let the sauce simmer for just a couple of minutes.

Return the browned beef to the pot along with any juices. Add 2 tablespoons of red wine vinegar and 1 tablespoon of honey. Cover and reduce heat to low, simmering gently for 1.5 to 2 hours.

After slow-cooking, taste and adjust seasoning as needed. Remove the cinnamon stick and bay leaves.

Ladle out the stewed beef stifado into bowls and garnish with freshly chopped parsley. Serve hot alongside crusty bread, rice, or mashed potatoes.