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Turn the slow cooker to low and heat 2 tbsp of the oil in a large frying pan. Season the meat and fry for 3-4 mins in batches until browned all over, scooping out each batch with a slotted spoon and transferring the browned meat to a plate.
Tip the onion, carrot and celery into the pan and fry for 5-10 mins until soft. Add the herbs and flour and cook for another 2 mins. Pour a splash of the wine into a bowl, then add the stock cube, sugar and tomato purée and mix to form a paste. Scrape the paste into the onion mix and pour in the remaining wine. Bring the mixture to a bubble, then transfer to the slow cooker. Stir in the browned beef, topping up with a splash of water to cover the meat if needed. Simmer on low for 6-8 hrs until the meat is falling apart but still holding its shape.
About 35 mins before serving, heat the remaining oil in a pan. Fry the bacon, shallots and mushrooms for 5-8 mins until caramelised and the veg is starting to soften, then tip into the slow cooker. Simmer the stew gently on high for 30 mins. If you want a thicker gravy, use the reduce function or leave the stew uncovered. Serve with mashed potatoes or crusty bread, if you like.