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Preheat oven on 450 degrees. Make roux: Heat oil in stockpot on MED-LOW. Gradually add flour while stirring with wooden spoon. Cook 75-90 min, stirring frequently at start of cook time. Stir constantly after roux starts to turn color until it's chocolate-brown. (Note: after 40 min cooking, roux should be peanut butter-color.) Roux will cook after removing from heat. Set aside.
Toss sausage with soy sauce in bowl. Roast 15-20 min on baking sheet in oven center rack, until caramelized and quite brown. Set aside.
Return roux to stovetop on MED-HIGH. Add garlic; cook 2-3 min, stirring constantly. Add tomatoes; cook, stirring, until slightly browned. Stir in thyme and 1 tsp basil. Add celery and onion; cook, stirring occasionally, about 3 min. Add chicken stock and Worcestershire sauce; bring to simmer. Add sausage; cook 10-15 min. Add peppers; cook 10 min. Add okra and chicken; season with Tabasco, salt, and remaining basil.
Make slurry: Whisk together gumbo file and water in small bowl; let stand about 1 min to thicken.
Remove gumbo from heat; fold slurry into gumbo with heat-proof rubber spatula and gentle lifting/ turning motion.
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