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Since 1992, the General Accountability Office placed the DoD contract management on the high-risk list due to the workforce’s lack of training, experience, and education. Their report found that budget constraints in the mid-1990s forced the DoD to reduce the acquisition workforce. The DoD began rebuilding its acquisition workforce in 2009. The Army founded the Army Contract Command (ACC) in 2008 to address issues in the contracting workforce. The ACC developed the 51C Proficiency Guide Assessment in 2010 and replaced the training guidance in 2019 with the 51C Job Aid. The purpose of this research was to identify the training requirements in each contracting environment including home-station, short-duration deployments, and long-duration deployments. This study used 22 of the 29 contract training tasks from the Job Aid and contracting data from the ACC Business Analyst Division to analyze the differences in tasks experienced between contracting environments. We captured the differences in each environment by accounting for the frequency of tasks performed in the environment. We concluded that the tasks performed in each contracting environment with varying frequency. The tasks contracting personnel executed in home-station were significantly different than the tasks they performed in deployment. Our study suggests that Army contracting should consider developing separate training plans that address tasks required to perform in each contracting environment.