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1
In a large pot over medium heat, add the oil. When the pan is hot, stir in flour using a hard plastic spatula to begin preparation of the roux.
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2
While preparing the roux, heat a pot of water with a teaspoon of sugar in it until it boils. Add corn and heat until bubbling again, then reduce heat to a simmer. Cover and cook for 8 minutes. Remove corn from water. When cool, cut kernels off the cob and set aside.
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3
Also while preparing the roux, heat seafood stock on low heat with shrimp shells and tails and any liquids that were retained from the oysters. Stir occasionally. Remove from heat when the roux is ready. Strain the shells and any other particles from the stock and set aside.
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4
Continue stirring and turning over the roux until the color resembles chocolate, about 30 minutes.
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5
Add the shallots, celery, and bell peppers, cooking for 5 minutes, stirring into the roux to ensure that every part is coated. Season with salt and pepper. Scrape the bottom of the pan and move the vegetables around so all of them have an equal amount of time on the bottom of the pot.
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6
Add the tomatoes, garlic, and chili peppers and cook for about 5 minutes, scraping and stirring as in the previous step.
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7
Stir in the stock, corn kernels, bay leaves, oregano, thyme, and Old Bay. Bring the liquid up to a boil, about 8 minutes. Reduce the heat to medium, and continue cooking for 15 minutes.
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8
While the stock is cooking, break the sausage into small pieces and cook in a separate pan until browned. Remove from pan and place on paper towel, but leave the rendered fat in the pan.
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9
Using the pan with the rendered fat, cook shrimp and oysters together with file powder on medium heat until cooked through, flipping over after a few minutes.
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10
Fold the shrimp, oysters, and sausage into the pot, reduce the heat and simmer for 5 minutes. Add water, increasing or decreasing to achieve desired consistency. Remove from the heat. Remove bay leaves and discard.
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11
To assemble, ladle the gumbo into a bowl with rice.
