The Department of Defense (DoD) significantly depends on private-sector contractors to assist with mission achievement, and obligates significant taxpayer dollars each year to contract support. Because of this, proper government contract surveillance and oversight is imperative to guarantee that the government is getting what it pays for. This research examined how the DoD can leverage technology to help contracting officer representatives (CORs) and contracting officers (COs) carry out proper contract surveillance. The research included a review of related literature and interviews with CORs, COs, and the leaders of CORs to describe current challenges. The results show that contract oversight and surveillance is a high-risk area because training is inadequate, because the COR role is often assigned as a collateral duty, and because of inefficiencies with eBusiness systems. This report offers recommendations that leverage technology to address these concerns and to improve contract oversight and surveillance across the department.