Season and Sear: Season the beef roast generously with salt and pepper. Heat olive oil in a large Dutch oven or heavy-bottomed pot over medium-high heat. Sear the roast on all sides until browned, about 4-5 minutes per side. Remove the roast and set aside.
Sauté Vegetables: In the same pot, add the chopped onion, garlic, carrots, and celery. Sauté for 5 minutes, stirring occasionally, until the vegetables begin to soften.
Deglaze and Simmer: Add the red wine (if using) and stir to deglaze the pot, scraping up any browned bits from the bottom. Then add the diced tomatoes, beef broth, tomato paste, thyme, rosemary, and bay leaf. Stir well.
Cook the Roast: Return the roast to the pot and cover. Reduce the heat to low and simmer for 3-4 hours, or until the roast is fork-tender and fully cooked. Alternatively, you can cook the roast in a preheated oven at 325°F (163°C) for the same amount of time.
Optional Gravy: Once the roast is done, remove it from the pot. If you’d like a thicker gravy, mix the cornstarch with water and stir it into the pot. Bring to a simmer and cook for 2-3 minutes until thickened.
For the Mashed Potatoes:
Cook the Potatoes: In a large pot, cover the cubed potatoes with water and bring to a boil. Cook for 15-20 minutes, or until the potatoes are tender when pierced with a fork.
Mash the Potatoes: Drain the potatoes and return them to the pot. Add butter, heavy cream (or milk), salt, and pepper. Mash until smooth and creamy.
Serve: Garnish the mashed potatoes with fresh parsley, if desired.
Serving and Storage Tips:

Pot Roast over Mashed Potatoes
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