As deepfake technology rapidly evolves, its application in social engineering has reached a new level of sophistication. This talk will explore a real-world red team engagement where AI-driven deep fake voice cloning was leveraged to test an organization’s security controls. Through extensive research, we examined multiple deepfake methods, from video-based impersonation for video calls to voice cloning for phishing scenarios. Our findings revealed that audio deep fakes were the most effective and hardest to detect by human targets.