In a large Dutch oven, heat 2 tablespoons of olive oil over medium-high heat until shimmering. Season your beef chuck roast with salt, pepper, and a light dusting of all-purpose flour. Add the beef pieces and brown them for about 10-12 minutes, turning occasionally to achieve a rich, golden color.

Once the beef is perfectly browned, stir in 2 tablespoons of tomato paste. Cook for around 2 minutes, allowing the paste to darken slightly and intensify in flavor.

Pour in 1 cup of red wine or red wine vinegar, using your spoon to scrape up any remaining bits stuck to the bottom. Let the mixture simmer for about 2 minutes.

Now, add 1 diced yellow onion, 2 chopped celery stalks, and 3 minced garlic cloves to the pot. Sauté these aromatic vegetables for 3-4 minutes, or until the onion becomes translucent and tender.

Stir in 2 diced carrots, 4 diced Yukon gold potatoes, 1 diced Granny Smith apple, 2 tablespoons of Worcestershire sauce, 1 cup of apple cider, and 4 cups of beef broth. Toss in 2 bay leaves and 1 teaspoon of fresh sage.

Once boiling, reduce the heat to low and cover the pot. Let the stew simmer for at least 1 hour, stirring occasionally.

After simmering, stir in 1 cup of fresh or frozen cranberries and taste the stew. Cook for an additional 10 minutes.

Once everything is cooked to perfection, ladle the cranberry apple beef stew into bowls. Garnish with freshly chopped parsley and serve hot.