The inability of the United States to capture or kill Osama bin Laden and many of his top deputies at Tora Bora is widely recognized as one of the most significant missed opportunities of America’s struggle with al Qaeda. However, the debate over U.S. actions at Tora Bora during Operation Enduring Freedom lacks in-depth analysis, especially concerning the commonly offered solution of more U.S. troops on the ground. This paper dissects the original operation against al Qaeda forces entrenched in the mountain complex in eastern Afghanistan in late 2001 and its impact on the debate over the Afghan model of warfare. An alternative plan involving U.S. conventional forces is presented that takes into account the considerable constraints of the scenario and analyzes the key make-or-break points of the operation. Although the challenges are far greater than most critics have allowed, the revised plan would likely have offered the best chance to capture or kill Bin Laden and a significant portion of the al Qaeda leadership.