Heat 1 tablespoon oil in a dutch oven over medium-high heat. Add the sausage and sauté for 5 minutes, until browned. Remove from pot and set aside.
Add 2 tablespoons oil to the stock pot. Add bell peppers, celery, jalapeno, onion, and garlic. Sauté for 6 minutes, stirring occasionally, until the onions are softened.
Add the crushed tomatoes, chicken stock, rice, Cajun seasoning, thyme, cayenne, and bay leaf, and stir to combine. Continue cooking until the mixture reaches a simmer. Then reduce heat to medium-low, cover to simmer for about 45 to 65 minutes, or until the rice is nearly cooked through, stirring every 5 minutes or so along the way so that the rice does not burn. Add more stock or water if necessary.
While jambalaya is cooking, heat remaining oil in a small pan. Add sausage, and cook for about 5 minutes, until browned.
When rice is almost done cooking add the shrimp, okra, and sausage and stir to combine. Continue to simmer, stirring occasionally, until the shrimp are cooked through and pink. Discard bay leaf.
Season with salt and pepper. You will likely need 1 or 2 teaspoons of salt depending on how salty your stock was.
Enjoy!