This case study analysis of three recent urban operations is intended to update the lessons learned from prior military experience. The three cases examined—Panama in 1989, Somalia in 1992-1993, and Chechnya in 1994-1995—all occurred within the last ten years and capture the range of political constraints that military forces must operate under in urban environments. The author discusses how ongoing technological, social, and political changes are increasing the significance of certain elements of urban operations. These include the presence of the media; the presence of noncombatants; rules of engagement; and information-operation tools such as psychological operations, public affairs, civil affairs, and political-military strategy.