This study examined obstacles to knowledge transfer and the factors that promote or inhibit knowledge transfer among information technology (IT) project managers in a defense industry organization. This knowledge is often transferred among project managers in the form of “lessons learned” systems that are intended to prevent the repetition of past mistakes and leverage the best practices of those in an organization. However, research has revealed that, although well-intentioned, these systems are rarely used (Weber et al., 2005). This study investigated knowledge transfer among IT project managers using a knowledge transfer questionnaire adapted from a Sverlinger 2000 study of knowledge transfer among construction industry technical consultants. It used sections of the 2000 questionnaire that addressed obstacles to knowledge transfer and organizational conditions enabling or facilitating knowledge transfer—structure, communications, process, culture, and systems for training and learning. One hundred and eleven project managers from a defense industry IT organization were invited to complete the questionnaire; 84 were completed. The findings revealed that although the organization possessed a willing and motivated workforce, many impediments to knowledge transfer exist. Lack of time, funding, training, and incentives were found to be major obstacles to knowledge transfer. Project lessons were not available to all within the organization, efforts were wasted through reinventing the wheel, and knowledge was difficult to locate. This study’s conclusions are consistent with the findings of other knowledge management researchers. However, because the study examined only one IT organization in the one industry, the results are not generalizable. Since knowledge reuse leads to improved organizational effectiveness and improves corporate profitability, the organization should use the results of this study as a tool for making improvements to their knowledge management program.