Season chicken with salt and pepper.

Heat 2 tablespoons oil in a heavy cast iron skillet. Sear chicken on both sides until golden, about 3-4 minutes each side. Remove from skillet and set aside.

Add remaining oil to the pan. Sauté the onion until transparent, about 3-4 minutes. Add in garlic and cook until fragrant, about 30 seconds. Add the peppers, carrot, mushrooms and herbs; cook for 5 minutes until vegetables begin to soften.

Pour in the wine, scraping up browned bits from the bottom of the skillet. Cook until wine is reduced, about 2 minutes.

Add crushed tomatoes, tomato paste, Roma tomatoes and chill flakes. Season with salt and pepper to your tastes. Return chicken pieces to the skillet and continue to cook over stove top OR in the oven following the instructions below.

FOR STOVE TOP:
Mix all of the ingredients together; cover with lid, reduce heat to low and allow to simmer (while stirring occasionally) for 40 minutes or until the meat is falling off the bone. Add in the olives, allow to simmer for a further 10 minutes. Garnish with parsley and serve immediately.

FOR THE OVEN:
Transfer the covered skillet to a preheated oven at 375°F (190°C) and cook for 50 minutes. Remove the lid, add in the olives and cook for an additional 20 minutes until the chicken is tender and falling off the bone, and the sauce has reduced.

If the sauce is too thin for your liking, add 2 tablespoons of extra tomato paste while it's simmering to thicken.

TO MAKE AHEAD: This chicken cacciatore can be made up to 1 day ahead, cooled, covered and refrigerated. Rewarm over low-medium heat.

TO FREEZE: Transfer the cooled cacciatore into an air tight container and transfer to the freezer. The day of serving, thaw it out in the morning and bring to room temperature. Transfer to a skillet / pan and reheat over low-medium heat until warmed through.