A majority of computer security breaches occur because internal employees of an organization subvert existing controls. While exploring the issue of violation of safeguards by trusted personnel, with specific reference to Barings Bank and the activities of Nicholas Leeson, this paper provides an understanding of related information security concerns. In a final synthesis, guidelines are provided which organizations could use to prevent computer security breaches. Businesses today are experiencing a problem with managing information security. This is so not only because of increased reliance of individuals and businesses on information and communication technologies, but also because the attempts to manage information security have been rather skewed towards implementing increasingly complex technological controls. The importance of technological controls should not be underplayed, but evidence suggests that the violation of safeguards by trusted personnel of an organization is emerging as a primary reason for information security concerns. Between 61 and 81% of computer related crimes are being carried out because of such violations (see Dhillon ; Dhillon and Backhouse  for a detailed discussion). These insiders could be dishonest or disgruntled employees who would copy, steal, or sabotage information, yet their actions may remain undetected.