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Despite more than a decade of significant government investment in network defense research and technology development, there have been relatively few successful transitions across the chasm between research and operational use. Prior work describes approaches to crossing the “valley of death” from the perspective of the government sponsor or independent tester. The researcher and developer's perspective offered in this paper adds to our understanding of the challenges faced and solutions applied to deployment of advanced technologies into operational environments. The paper describes lessons learned from recent transitions of two information assurance technologies - the VIAssist® netflow visualization tool and the MeerCAT® wireless vulnerability analysis tool - into operational use by the Department of Homeland Security (DHS) and the Department of Defense (DoD).