Heat the ½ cup vegetable oil in a large Dutch Oven or heavy-bottomed Pot over medium heat. Once shimmering, whisk in the ½ cup all-purpose flour until smooth. Switch to a Wooden Spoon or heat-safe Spatula.

Cook the roux, stirring constantly and scraping the bottom of the Pot, for 25–35 minutes. You're aiming for a deep chocolate-brown color — like dark milk chocolate or a copper penny. Don't rush this step and don't walk away. If it smells burnt, reduce the heat.

Rinse peppers under cold water and pat dry. Slice off tops and bottoms, stand upright, and cut down along the inside to remove seeds and white ribs. Slice lengthwise into ½-inch strips; halve crosswise for shorter pieces. Keep sizes uniform so everything cooks evenly. If adding onion, slice it now. Measure out olive oil, salt, and pepper. Have everything ready before the pan goes on — sautéing moves fast.

Heat a large Skillet over medium heat. Add 1 tbsp olive oil per 2 peppers; warm 30–60 seconds until shimmering. Add pepper strips in a single layer — work in batches if crowded. Season with salt and pepper, stir to coat. Cook over medium heat, stirring every 2–3 minutes, for 6–10 minutes. At 6 minutes: slightly softened with snap. At 10 minutes: tender throughout with light color. For very soft peppers, cook 30–40 minutes over medium-low, stirring occasionally. Add garlic halfway through cooking. If browning too fast, add a splash of white wine or water and briefly cover to steam.

Add the minced 5 cloves garlic minced and cook for 1 more minute, stirring constantly, until fragrant.

Rinse peppers under cold water and pat dry. Slice off tops and bottoms, stand upright, and cut down along the inside to remove seeds and white ribs. Slice lengthwise into ½-inch strips; halve crosswise for shorter pieces. Keep sizes uniform so everything cooks evenly. If adding onion, slice it now. Measure out olive oil, salt, and pepper. Have everything ready before the pan goes on — sautéing moves fast.

Heat a large Skillet over medium heat. Add 1 tbsp olive oil per 2 peppers; warm 30–60 seconds until shimmering. Add pepper strips in a single layer — work in batches if crowded. Season with salt and pepper, stir to coat. Cook over medium heat, stirring every 2–3 minutes, for 6–10 minutes. At 6 minutes: slightly softened with snap. At 10 minutes: tender throughout with light color. For very soft peppers, cook 30–40 minutes over medium-low, stirring occasionally. Add garlic halfway through cooking. If browning too fast, add a splash of white wine or water and briefly cover to steam.

Add the 1 ½ lb boneless skinless chicken thighs cut into 1-inch pieces, all of the spice blend ingredients (2 tsp Cajun seasoning, 1 tsp smoked paprika, 1 tsp dried thyme, 1 tsp dried oregano, ½ tsp black pepper, ¼ tsp cayenne pepper add more, 2 tsp kosher salt plus more, 2 tsp Worcestershire sauce, and 2 piece bay leaves), and stir well to coat everything evenly.

Rinse peppers under cold water and pat dry. Slice off tops and bottoms, stand upright, and cut down along the inside to remove seeds and white ribs. Slice lengthwise into ½-inch strips; halve crosswise for shorter pieces. Keep sizes uniform so everything cooks evenly. If adding onion, slice it now. Measure out olive oil, salt, and pepper. Have everything ready before the pan goes on — sautéing moves fast.

Heat a large Skillet over medium heat. Add 1 tbsp olive oil per 2 peppers; warm 30–60 seconds until shimmering. Add pepper strips in a single layer — work in batches if crowded. Season with salt and pepper, stir to coat. Cook over medium heat, stirring every 2–3 minutes, for 6–10 minutes. At 6 minutes: slightly softened with snap. At 10 minutes: tender throughout with light color. For very soft peppers, cook 30–40 minutes over medium-low, stirring occasionally. Add garlic halfway through cooking. If browning too fast, add a splash of white wine or water and briefly cover to steam.

Simmer uncovered for 40–45 minutes, stirring occasionally, until the 1 ½ lb boneless skinless chicken thighs cut into 1-inch pieces are very tender and the gumbo has thickened and deepened in flavor. Skim any excess fat or foam from the surface as needed.