Set your oven to 375°F (190°C) to begin heating.
Place the chicken breasts between sheets of plastic wrap or parchment, then gently tap them with a meat mallet until they’re evenly flattened.
Brush the chicken with olive oil and generously season both sides with salt, pepper, thyme, garlic powder, and onion powder.
Carefully slice a horizontal pocket into the thickest part of each chicken breast without cutting all the way through.
Fill each pocket with a good spoonful of cranberry sauce and several pieces of Brie cheese, then press the edges firmly to close them.
Warm a large oven-safe skillet over medium-high heat and add a bit of olive oil.
Sear the stuffed chicken breasts in the skillet until each side turns a golden brown, about 2 to 3 minutes per side.
Transfer the skillet straight into the preheated oven and bake for 20 to 25 minutes until chicken is cooked through, reaching an internal temperature of 165°F (74°C).
Once baked, let the chicken rest on a plate for a few minutes before cutting it into slices.
Serve your cranberry and brie stuffed chicken with your favorite sides like roasted veggies or a fresh salad to complete the meal.