The authors describe an approach for leveraging machine learning to support assessment of military operations. They demonstrate how machine learning can be used to rapidly and systematically extract assessment-relevant insights from unstructured text available in intelligence reporting, operational reporting, and traditional and social media. These data, already collected by operational-level headquarters, are often the best available source of information about the local population and enemy and partner forces but are rarely included in assessment because they are not structured in a way that is easily amenable to analysis. The machine learning approach described in this report helps overcome this challenge. The approach described in this report, which the authors illustrate using the recently concluded campaign against the Lord's Resistance Army, enables assessment teams to provide commanders with near-real-time insights about a campaign that are objective and statistically relevant. This machine learning approach may be particularly beneficial in campaigns with limited or no assessment-specific data, common in campaigns with limited resources or in denied areas. This application of machine learning should be feasible for most assessment teams and can be implemented with publicly and freely available machine learning tools pre-authorized for use on U.S. Department of Defense systems.