This workshop dives into real-world social engineering attacks and corporate espionage incidents, examining how they unfolded, what failures enabled them, and the human and organizational factors at play. The session will begin with detailed case studies from recent history, followed by structured thought experiments to explore root causes, attacker motivations, and mitigation strategies. The workshop will also include facilitated discussion with participants to analyze scenarios, share experiences, and collaboratively identify practical defenses against social engineering and insider threats.