Preheat the oven to 250 degrees F.
Heat the olive oil in a large dutch oven over medium high heat. Add the bacon and cook until the fat renders and the bacon is crisp, about 5 minutes. Remove the bacon with a slotted spoon and place on a large plate.
Dry the beef with paper towels and season with salt and pepper. Now add the beef to the dutch oven and sear in batches until the beef is browned all over, about 3-5 minutes. Transfer the beef to the plate with the bacon. Set Aside.
To the dutch oven with the drippings, add the onions and season with salt and pepper. Cook until soft and translucent, about 5 minutes. Add the carrots and garlic and cook 30 seconds to 1 minute, then add the cognac and raise the heat to high. Cook until reduced by half, about 5 minutes. Next, add the meat and all the juice on the plate back to the dutch oven. Add the wine, beef broth, tomato paste, thyme, and bay leaves. Bring to a simmer over high heat. Remove from the heat and stir in 1 cup of cranberries. Cover with a tight fighting lid and transfer the pot to the oven. Cook for 2 hours or until the meat is tender is shreds easily with a fork.
Remove the pot from the oven and place over medium heat on the stove. Combine the 2 tablespoons butter and the flour until a smooth paste forms. Stir the paste into the stew. Add the remaining 1 cup cranberries and cook until the stew thickens just slightly.
Meanwhile, melt the remaining 2 tablespoons of butter in a large skillet over high heat. Add the mushrooms and season with salt and pepper. Cook until the mushrooms are just browned and caramelized, about 5 minutes. Stir the mushrooms into the stew and cook another 10 minutes. Season to taste with salt and pepper.
Serve over [mashed potatoes | https://www.halfbakedharvest.com/crockpot-three-cheese-mashed-potatoes/], egg noodles or crusty bread.