Despite years of awareness training and security investment, email remains one of the most effective attack vectors in cybersecurity. In this conversation, Ryan Toscano discusses why organizations continue struggling with phishing, impersonation, and social engineering at scale. The interview examines the tension between security, usability, and customer trust, the operational fatigue created by overwhelming security telemetry, and whether organizations are still treating email security too much as a technical problem instead of a human one.