The immense complexity of designing, developing, and maintaining Information Technology (IT) systems has been widely noted. One or more problems may occur with local workstations, their connection to a network, the network itself, its connection to receiving workstations, the receiving workstations, user error or misbehavior (inadvertent or intentional), and even the actions of IT technicians themselves. The range of material that IT technicians must master ranges from basic computer and network hardware, through ever-changing operating system, network, and application software, to a variety of client services, permissions, and administration. US Navy ships are increasingly dependent upon IT systems, which has created an urgent and growing need to accelerate the development of IT expertise. Tutorial instruction has been shown to both accelerate and deepen learning, but providing a single human tutor for each of the 1500-2000 sailors receiving IT “A” school certification training each year is unaffordable. Digital (computer-based) tutoring systems may offer a solution. Assessments of a DARPA Digital Tutor project have found that it can in 16 weeks produce sailors whose IT knowledge and troubleshooting capabilities substantially exceed those of other sailors receiving 35 weeks of classroom instruction and those of experienced ITs with 7-9 years of experience in the Fleet. These findings suggest both monetary and operational value in terms of cost-effectiveness and return on investment over current education and training practices in IT and related areas.