The tragic events of 9/11 highlighted failures in communication and cooperation in the U.S. intelligence community. Agencies within the community failed to “connect the dots” in the intelligence they had, which was cited by the 9/11 Commission Report as a reason for the terrorist attacks being allowed to happen. Since then, the U.S. intelligence community has made organizational and operational reforms towards intelligence sharing. As part of this reform, the Director of National Intelligence has introduced web-based social computing technology to be used by all members of the intelligence community. This paper argues that while this technology has been adopted into the intelligence environment, it has reached a “plateau” in its use, and that intelligence failures continue to persist in the U.S. post-9/11 world. It identifies and analyzes the challenge of implementing social computing and Web 2.0 technology into the U.S. intelligence community, as well as account for possible deficiencies in the community that might be contributing to these intelligence failures. Finally, the definition of “success” in intelligence analysis and social computing is explored, and critique against information sharing is put forth.