We explore the potential legal and technical risks inherent in attempts to implement digital protection. Specifically, we consider how liability might arise for those who have fiduciary responsibility for sensitive information assets, including the emerging trend toward imposing liability where digital protections are severely deficient or digital security has been breached. We also focus on obstacles created by disparities in the knowledge and expertise of professionals who are responsible for corporate assets and who risk legal liability if their efforts are insufficient or ineffective. We address these disparities to bridge the gap between executive personnel responsible for corporate governance and technical personnel responsible for corporate digital security