The increasing use of wooden cladding in multi-storey buildings raises critical fire safety concerns, especially in ventilated façade systems where the chimney effect can accelerate vertical flame spread. This study combines theoretical analysis with three full-scale fire tests to investigate key factors influencing fire propagation, including the influence of façade design details. Results show that poorly constructed lintels and jambs significantly accelerate flame entry into ventilated cavities, while wooden fire barriers—despite being combustible—can delay flame spread if properly installed. These findings inform design recommendations and underscore the need for more robust fire safety strategies in modern timber construction.