This will be a case study of the little known Fetterman Massacre of 1866. It will look the situation at the time, possible causes, key players, the massacre itself and the aftermath. Similarities to the counterinsurgency in Afghanistan will be noted where applicable throughout this paper. A case will be proposed that the Army was ill prepared for the Indian Wars of the latter 19th Century, just as they were initially ill prepared for an extended Afghanistan Insurgency Campaign. Connections are drawn showing that there were lessons learned in 1866 that are still appropriate today. Familiarity with them, along with other more recent examples, will better prepare the Army to fight counterinsurgencies in the future.