Information Technology is as vital and ubiquitous in the national economy as it is in military operations. A 16-week Digital Tutor for the Navy Information Systems Technicians (IT) rating was produced for DARPA as a way to accelerate the development of expertise in IT and related areas. Graduates from the DARPA Tutor program were found by independent, third-party assessment to exceed significantly (p < 0.01) and practically (effect sizes ranging as high as 3.00 standard deviations) the knowledge and practical troubleshooting skills of IT graduates with 35 weeks of classroom training and sailors averaging over 9 years of IT experience in the Fleet. The Tutor was revised and extended to 18 weeks in order to include preparation for higher-level IT certifications and topics relevant to civilian employment. Ninety-seven veterans have completed the newer 18-week version. Eighty-three of these veterans were unemployed after an average 5 years of separation from active duty. There were no academic dropouts from the course. Nearly all who sought employment after finishing the course have found jobs averaging $65,000 per year. This paper briefly reviews learning and economic findings from the Navy assessments, and provides up-to-date information on learning, quality of life, and economic findings from the veterans' project, including returns to government investment at various scales of implementation. It also provides an overview of strategies underlying intelligent tutoring systems, those used to develop the Digital Tutor, and practical tactics the Tutor applies to accelerate acquisition of technical expertise. This paper is important to the community because it addresses an important topic (Information Technology); the promise of the Tutor's technology; the perennial military need to accelerate development of technical expertise; the magnitude of the assessment findings; and the responsibility to prepare people likely to be separated from the military in the near future.