Developing software within the DoD presents a unique set of challenges, including but not limited to budget cuts, Congressionally mandated changes, changing software requirements, and so on. It should come as no surprise, therefore, that cost estimators have faced significant challenges when estimating systems in the Defense arena. A recent initiative put forth by the DoD was to improve its estimation process by leveraging historical data collected from forensic analyses of recently completed software development efforts. This article by Taylor Putnam-Majarian and John Staiger, discusses (1) some of the challenges faced throughout this initiative, (2) the data collection process, and (3) how one can leverage data to improve cost estimates. This article was originally published in Crosstalk Magazine.