The Air Force Studies Board of the National Academies of Sciences, Engineering, and Medicine hosted a three-part workshop series to examine the risks associated with the technical, programmatic, organizational, and governance challenges facing the Department of the Air Force (DAF) in its pursuit of enterprise-wide digital transformation strategies. Senior representatives from government, military, industry, and academia considered the DAF''s strategic-level decision-making process as well as how it could achieve unity of effort across all of its digital agencies. Workshop participants discussed organizational and management gaps and weaknesses, as well as technical shortfalls associated with the DAF''s digital transformation strategies - for example, the issue of cybersecurity within the context of the DAF''s proposed digital strategies. Organizational and management practices from both the public and private sectors were also discussed in light of their potential for adaptation and adoption within the DAF.

Sponsored by the U.S. Department of Defense, the three 2-day workshops of the series were held virtually on September 1-2, 2021, September 8-9, 2021, and September 23-24. Panelists at the first workshop explained and discussed the DAF''s digital transformation strategy - in particular, the proposed digital architectures and the systems, programs, organizations, and missions to be supported. The second workshop featured panels of information systems experts and managers from industry and other government agencies who discussed their experiences with digital transformations and shared their views of best practices. The third workshop focused on the potential applicability of these lessons learned to the DAF''s digital transformation strategy and architecture. This proceedings is a factual summary of what occurred during the workshop series.