Prepare the Beef: Trim off any hard fat or silver skin from the 2 pounds beef chuck roast. Cut into 1 to 1½-inch cubes. Set aside.
Coat the Beef: In a large 1-gallon resealable bag, combine the 1/4 cup all-purpose flour, 1 teaspoon paprika, 1 teaspoon coarse ground black pepper, and 1 teaspoon kosher salt. Add the cubed beef, seal the bag, and shake until the beef is evenly coated.
Sear the Beef in Batches: Heat 2 tablespoons extra virgin olive oil in a large Dutch oven over medium-high heat. Once hot, add 2 tablespoons unsalted butter. When the butter melts, add half of the floured beef cubes, shaking off any loose flour first. Sear each piece on all sides, turning every 3–5 minutes, until browned. Transfer browned beef to a plate and repeat with remaining beef.
Sauté the Aromatics: Once all the beef is seared and removed from the pot, reduce heat to medium. Add 1 shallot, diced and 3 garlic cloves, minced . Cook for 3 minutes, stirring often, until fragrant and translucent.
Deglaze the Pot: Pour in 1 cup Cabernet Sauvignon and scrape up any browned bits from the bottom of the pot. Stir in 4 cups 32 ounces beef stock (I love Kitchen Basic), 2 teaspoons Worcestershire sauce, 1 tablespoon dried Italian seasoning, and remaining 1 teaspoon kosher salt.
Simmer the Beef: Return the seared beef to the pot. Stir everything together, cover with a tight-fitting lid, and bring to a boil. Once boiling, reduce heat to low and simmer for 40 minutes, covered.
Add Vegetables: While the soup simmers, chop 4 cups red potatoes and 3 cups baby carrots into bite-size pieces. After 40 minutes, add them to the pot. Stir well to coat with broth. Cover and simmer for an additional 40 to 50 minutes, or until the vegetables are fork-tender and the beef is melt-in-your-mouth tender.
Taste and Adjust: Taste the broth and adjust salt if needed. Garnish with chopped Fresh parsley, if desired. Serve hot with crusty bread or a side salad.
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Notes
Make-Ahead Tips: You can prepare the beef and broth mixture up to 1 day ahead. Store in the refrigerator and reheat gently before adding vegetables.Storage: Cool soup completely, then transfer to airtight containers. Store in the refrigerator for up to 4 days.Freezing Tips: This soup freezes beautifully. Freeze in individual portions or a large container for up to 3 months. Leave some space at the top of the container for expansion.Reheating: Reheat in a saucepan over medium-low heat, stirring occasionally until warmed through. You can also reheat individual servings in the microwave in 30-second intervals, stirring in between.Ingredient Tips: Beef: Chuck roast, chuck shoulder, chuck-eye roast, or top chuck work best. Do not use pre-cut stew meat—it's often a mix of tough cuts.Wine Substitute: If avoiding alcohol, substitute the wine with additional beef stock or grape, pomegranate, or cranberry juice.DIY Italian Seasoning: If you don’t have a premade blend, use 1 teaspoon dried basil, 1 teaspoon dried rosemary, 1/2 teaspoon dried oregano, and 1/2 teaspoon dried thyme.Stock Substitute: Substitute 4 teaspoons beef base or bouillon plus 4 cups water if needed.