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Adjust oven rack to center position and preheat oven to 450°F. Season chicken generously with salt and pepper. Heat 1 tablespoon oil in a large skillet over high heat until lightly smoking. Add chicken pieces skin side-down and cook, moving chicken as little as possible, until chicken skin is rendered and deep golden brown, 8 to 12 minutes, reducing heat if smoking excessively. Flip pieces as they finish and lightly brown second side, about 3 minutes longer. Transfer browned chicken pieces to a plate and set aside. Add remaining tablespoon oil to skillet and add carrots and squash. Cook, stirring, until lightly browned, about 4 minutes. Add shallots and cook, stirring, until fragrant, about 1 minute. Add cinnamon and broth. Nestle chicken pieces into pan skin side up and transfer to oven. Roast until chicken registers 165°F on an instant read thermometer, about 30 minutes. Remove from oven. Transfer chicken to a plate. Stir lemon juice and cilantro into vegetables and season to taste with salt and pepper. Return chicken to skillet and serve.
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