Make the Roast

1. Preheat oven to 450˚F. Pat roast dry with paper towels. Tie roast with butcher twine if desired for more even cooking (I had the butcher do this for me at the meat counter). Place in an oven safe, large skillet.
2. Brush roast evenly with olive oil.
3. Mix pepper, salt, herbs, and garlic until completely combined in a small bowl. Sprinkle the mixture evenly all over the roast, patting it gently to help it stay.
4. Insert a meat thermometer through the side into the center of the roast. Place skillet on the middle rack in the preheated oven.
5. Cook for 15 minutes and then reduce the temperature to 350˚F. Cook another 45 minutes to 1 hour, until internal temperature reaches desired level of doneness: 135˚F for medium rare, 140˚F for medium.
6. Remove skillet from oven and place on the stove. Remove meat thermometer and place roast on a plate and cover with a foil tent. Let rest for 15 minutes. The roast will continue to cook internally as it rests, reaching 140˚F for medium rare, 145˚F for medium.

Make the Sauce

1. While the roast is resting, make the sauce. In the same skillet used to cook the roast, pour in one tablespoon of the wine over medium high heat. Scrape up any browned bits on the bottom of the pan.
2. Melt butter in the skillet. Add the mushrooms and sauté, stirring frequently, until mushrooms have softened and released their juices, about 8 minutes.
3. Add tomatoes, half of the herbs, and garlic. Sauté one minute, until garlic is fragrant.
4. Stir in flour, cooking until golden, about 1-2 minutes.
5. Pour remaining red wine into the pan, scraping any browned bits off the bottom of the pan.
6. Pour in chicken broth, stir to combine, and bring to a boil. Lower heat to a simmer and cook 2-3 minutes, until somewhat thickened.
7. Still on low heat, slowly pour in milk and warmed cream. Add fresh herbs and stir to combine. Bring to a simmer. Cook until sauce is somewhat thickened, about 2-3 minutes.
8. Remove from heat. Add salt and pepper to taste.

Serve the Roast

1. Plate roast and drizzle with mushroom tomato skillet sauce. Slice thinly as desired
2. Garnish with any remaining fresh herbs, ground black pepper and finishing salt. Serve and enjoy!
3. Leftovers can be kept in an airtight container for up to 3 to 4 days in the fridge. The leftovers of this roast is perfect for roast beef sandwiches!