The Department of Defense (DOD) is quickly reaching an information technology (IT) crossroad; its choices will determine whether it achieves decisional superiority or becomes paralyzed and drowns in its own data. Information management technologies and practices currently used to exploit the exponentially growing volumes of data are rapidly becoming inadequate. For instance, a battalion intelligence analyst requires time-critical information spread across 200 different networks in 20 different languages. Upon uncovering a bad lot of batteries, a satellite program manager must survey 15 different contracts' as-designed and as-built lists to ensure none of the faulty batteries are used. A deployed commander cannot write his or her subordinates' promotion recommendation forms because the local area network does not host the requisite form's viewer software. A Marine platoon commander's intelligence requirements change as he moves from stateside training, to forward base operations, to patrol. These users must access and manipulate unstructured data, obtain and share contextually relevant information, and operate from and across dissimilar IT systems. Effective information management capabilities are a critical requirement, not a luxury. In their testimony to the Senate Committee on Homeland Security and Governmental Affairs, representatives of the Government Accountability Office (GAO) stated that "the ability to find, organize, use, share, appropriately dispose of, and save records-the essence of records management-is vital for the effective functioning of the federal government." Beyond meeting basic information management capabilities, the DOD requires the ability to simultaneously and remotely share maps, imagery, and video among commanders at all echelons across mounted or dismounted ground terminals and airborne and seaborne assets to support decision making. The DOD's underlying problem is the inability to collect, gather, organize, exploit, share, and store data that comes from multiple dissimilar systems, venues, and media. Dissimilarity transforms carefully structured data into unintelligible unstructured data. Structured data is organized into a format that an individual user's software can read. If that format is then unrecognizable to a different individual's software, the data, no matter how innately valuable, becomes unstructured and is rendered worthless. This is a problem when considering the approximately 281 billion exabytes of data in cyberspace as of 2006. By 2011 this number is expected to increase by a factor of 10. With a wealth of data tied to incompatible formats and buried within a multitude of evolving networks, the unifying problem becomes how the DOD can best posture itself technologically and doctrinally to harness the rapid growth of unstructured data and infrastructure to achieve mission success. Though many organizations share this problem, military requirements tend to be more challenging than commercial and civilian requirements. The combination of mission diversity, changing operational environments, and the variety of joint and coalition electronic formats and architectures available pose IT challenges more complex than those faced by shipping, health care services, manufacturing companies, and other civilian business sectors or private use. This paper goes beyond identifying singular technologies and implementation strategies to propose a comprehensive solution construct called the "Virtual Wingman." The Virtual Wingman construct demonstrates how current and nascent technologies and practices can be integrated and tailored to contextually provide the right information at the right time and in the right form. The Virtual Wingman is not a point solution. Rather, it embodies capabilities the DOD must develop and embrace to avoid decisional and operational paralysis when faced with mounting volumes of unstructured information and increasingly complex systems of systems.