Private sector U.S. defense contractors failing to meet contract objectives experience lower profitability, pay costly penalties, and risk survivability. Using the theory of contracts, the purpose of this multiple case study was to the explore strategies that some leaders of U.S. defense contracting businesses use to meet all the contract terms with the U.S. Department of Defense. Data were collected from 5 leaders of private sector defense contracting companies in northwest Florida through face-to-face, semistructured interviews and through a review of operations manuals, quality assurance policy manuals, and archived U.S. Department of Defense contracts. During data analysis using Yin's 5-step process of compiling, disassembling, reassembling, interpreting, and concluding the data, 4 themes on strategies emerged: (a) communication strategy for successful completion of contracts, (b) technology strategy to monitor contract compliance, (c) training strategy for program managers, and (d) subcontractor selection strategy. The findings indicated that communication among all contract parties was an essential component of each of the 4 themes. Computerizing the contracting workflow to monitor compliance efforts, training program managers for effective oversight of contract compliance, and selecting subcontractors were vital elements of the strategies private sector defense contractors used to meet all the terms and conditions of U.S. Department of Defense contracts. The implications for positive social change include the potential for private sector defense contractors to improve the strength of the defense of the northwest Florida community, lower unemployment, and provide a safer environment for humanity.