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Preheat oven to 350 degrees F.
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In a heavy pot or Dutch oven, cook the bacon until crisp. Remove from pan with a slotted spoon. Season the short ribs with salt and pepper and add them to the pan. Cook until well browned on both sides, and remove from the pan.
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Add the olive oil and cook the onion, shallots, and carrot until softened, scraping the browned bits from the bottom. Add the short ribs back to the pot, along with the broth. Add additional water if necessary to make sure short ribs are about 3/4 covered. Add the herbs and garlic cloves and cover.
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Put in the oven and cook for about 2 hours. Turn the heat down and cook for another 45 minutes, or until ribs are falling apart with a fork.
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Just before ribs are done, make the cauliflower. First, steam the florets and garlic cloves until very soft, either in a vegetable steamer basket or the microwave.
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Put the cauliflower and garlic in a food processor with the milk and half the butter. Puree until smooth and creamy and stir in the remaining butter and rosemary before serving.
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Serve the short ribs with the mashed cauliflower.