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Preheat oven to 180°C (160°C fan-forced).
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Heat 1 tbsp oil in a large (4 L) flameproof, ovenproof heavy-based casserole pot over high heat. Cook beef, in batches, until browned, adding a little more oil between batches if needed. Transfer beef to a bowl.
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Add bacon to pot, cook stirring for 2 mins or until browned. Add to bowl with beef. Add 1 tbsp oil. Add mushrooms and cook for 3 mins until golden. Add to bowl with beef and bacon.
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Heat remaining 1 tbsp oil in pot over medium heat. Add onion and carrot. Cook, stirring occasionally, for 6 mins, scraping the caramelised bits from the bottom of pot. Add garlic, and cook, stirring for 1 minute. Add tomato paste and cook, stirring for 1 minute. Sprinkle over flour then cook, stirring, for 2 mins.
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Place boiling water into a large heatproof jug, add red wine stockpots and stir until stockpots dissolve. Remove pot from heat. Slowly pour in the red wine stock mixture into pot, while stirring continuously, until well combined and flour dissolved. Stir in thyme, rosemary and bay leaves. Add reserved mushrooms, beef and bacon. Season with pepper. Bring to a simmer, stirring. Cover then transfer to oven and cook for 2 1/4 hours, or until beef is fall apart tender. Remove and discard bay leaf. Serve with mashed potato.