The US Army has published several documents and directives that establish the overarching strategies, guidance, and an implementation plan for the rationalization and modernization of the Army’s information technology (IT) systems and applications. The guidance and implementation plan mandate a Business Case Analysis (BCA) be performed when assessing the migration of IT systems and applications to approved hosting environments, and closing or consolidating data centers. These overarching strategies, guidance, and implementation directive impact how the Army’s Integrated Training Environment (ITE) will be hosted in the future. The individual training devices and simulations that comprise the ITE have existed for some time, and some of the architectures may not support effective homestation training if they are hosted in a distant enterprise data center. This paper reports on the analysis performed to assess the main systems that comprise the ITE System of Systems (SoS), and conduct a BCA in accordance with the Army guidance. The technical assessment framework that was developed for the characterization and technical assessment of training and simulation systems is described. The paper then discusses how the framework was utilized to characterize and assess each of the systems, including critical system-of-systems aspects, and generate the technical rationale for feasible cloud migration alternatives. The approach and methodology for the BCA are described, and the calculated cost and economic viability are presented for each of the feasible migration alternatives. Sensitivity analysis results are shown illustrating the extent to which alternative rankings change as a result of varying certain factors and/or assumptions. Finally, the paper discusses how the technical assessment and BCA provide PM ITE with the information necessary to support planning, budgeting, and architectural evolution for the migration of the ITE to the cloud.