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Preheat the oven to 350°F with a rack in the center position.
Add the bacon to a Dutch oven and cook over medium, stirring occasionally, until the bacon is just crisp, about 6 minutes.
Using a slotted spoon, transfer the bacon to a paper towel-lined plate.
Add the mushrooms and a pinch of salt and pepper to the Dutch oven. Increase heat to medium-high and cook until the mushrooms are browned, about 3 minutes.
Scrape browned bits off bottom with wooden spoon. Using a slotted spoon, transfer the mushrooms to a large bowl.
Pat the beef chuck roast pieces dry with a paper towel. Season all over with 2 teaspoons kosher salt and lots of coarsely ground pepper.
Heat the vegetable oil over medium-high. Working in batches, add beef and cook over medium-high, until browned on two sides, about 4 to 5 minutes per side.
Transfer the browned beef to the bowl with the mushrooms. Repeat with the remaining beef.
Carefully spoon off all accumulated fat from the Dutch oven.
Add the butter, garlic cloves, and the tomato paste to the Dutch oven. Cook over medium-high until the butter has melted, about 30 seconds.