This chapter provides a managerially oriented analysis of the risk factors involved as Information Technology becomes a more integral part of jobs on both an operational and managerial level. The chapter will summarize the human side risks of IT-enabled jobs, especially in organizations that have used IT to restructure more traditional jobs. Topics will include the following categories of risk. First, the risks of using IT to create combined “case manager” jobs, recommended by reengineering advocates (Davenport & Nohria, 1994) will be examined. Employees in these positions must assume greater accountability for their work and often find their jobs more stressful and demanding than their predecessors. Another problem with combined jobs is the loss of separation of duties that arises when jobs are combined. Secondly, the risks of using IT to reduce the numbers of levels of management will be examined. Reengineering advocates call for organizations to eliminate levels of middle management and create flatter, more efficient structures. As a result, managers in reengineered organizations are also likely to suffer from the information overload, rising job demands, and stress that operational level employees do. Internal control theory also expresses concern about the potential for managerial fraud and warns organizations to be on the lookout for “pressures and opportunities” that would drive an individual in a position of trust to do serious damage (Cushing & Romney, 1999).