The sharing of information across government intra- and inter-agencies provides enormous benefits to Intelligence operations, but it also poses risks to Intelligence organizations’ operational capability. These benefits and risks of sharing information within Intelligence Communities introduce a paradox that disturbs decision-making abilities and affect existing and future relationships with local and national Intelligence partners. With this paradox, there exist particular forces that affect the paradox, such as organizational factors and the behavior of an information sharer, the responsible actor that decides on how, when and with whom to share the information. Combining the two can produce a positive (desired) outcome that leads to successful mission accomplishment or negative (inadvertent) outcome that leads to loss of information disclosed or intentional loss of valuable information. An inadvertent outcome could result in an impact to the national defense of the United States. Do Intelligence Analysts share information when the risks outweigh the benefits? This research examines how understanding the paradox of information sharing is a critical element in understanding the behavior of Intelligence Analysts’ decision-making in Intelligence operations.