This research looks at the issue of risk tolerance, and analyzes its role in U.S. Army Special Forces (SF). More specifically, it assesses the degree to which senior members of an organization allow junior members to make autonomous decisions, and argues that the unconventional warfare (UW) mission and nature of SF call for a higher degree of risk tolerance than is seen in conventional forces. A longitudinal case study of the conflict in Afghanistan shows that in 2001 SF had a "long leash" to allow for autonomy and flexibility, which was necessary to succeed in a UW environment. However, by 2006, the leash was shortened and more control measures were implemented. While a "short leash" may be appropriate for a conventional battlefield, it adversely impacts SF effectiveness in a UW environment. The three main reasons that induce risk aversion in SF leaders are exogenous political factors, organizational considerations including chain of command, and organizational culture, which is reinforced by the current Army officer evaluation system. This analysis suggests that the deleterious impact of these factors needs to be addressed in SF.