This descriptive study explores the evolution of the Iraqi insurgency in the dynamic strategic environment between 2004 and 2006. In these three years, insurgents in Iraq sought to exploit terrorism as a tactic to induce fear and advance their regional and political agenda in the volatile Iraqi province of Diyala. Their geopolitical agenda was primarily aimed towards derailing the interim political process and reconciliation efforts throughout Iraq. This article draws its analytical conclusions from quantitative data of terroristic incidents, focusing on insurgents’ tactics, targeting of victims, and areas of activity. It examines trends of insurgent activity between 2004 and 2006 as well as the evolution of their strategy against the Iraqi Government and its people.