Preheat your oven to 325°F (160°C).

Heat olive oil in a large Dutch oven over medium-high heat. Season the bottom round roast with salt and pepper, then sear it in the hot oil until browned on all sides, about 4-5 minutes per side. Remove the roast and set aside.

In the same pot, add the sliced onion and cook until caramelized, about 8-10 minutes. Add the minced garlic and continue cooking for another 2 minutes until fragrant.

Pour in the Madeira wine, scraping the bottom of the pot to deglaze. Let it simmer for 3-4 minutes to reduce slightly.

Return the roast to the pot, then add the beef broth, Worcestershire sauce, and thyme sprigs. Bring the liquid to a simmer, cover the pot, and transfer it to the preheated oven.

Braise the roast in the oven for about 2.5 to 3 hours, or until the meat is tender and easily pulls apart with a fork.

While the roast is braising, prepare the rutabaga. In a large pot, cover the diced rutabaga with water and bring to a boil. Cook until tender, about 15-20 minutes. Drain and return to the pot.

Add heavy cream, chopped parsley, and tarragon to the cooked rutabaga. Mash until smooth and creamy. Season with salt and pepper to taste.

Once the roast is done, remove it from the oven and let it rest for 10-15 minutes before slicing.

Strain the braising liquid, discarding the thyme sprigs and any solids, then return the liquid to the pot and reduce it over medium heat for about 5-10 minutes to thicken slightly.

Serve the sliced roast topped with the rich Madeira glaze alongside the creamy rutabaga and herb gravy.