This article investigates the future of conflict in urban terrain, considering both trends in the operating environment and likely advancements in enemy capability as contributing to irregular threats. These trends are identified in theoretical terms and then examined in a hypothetical operation with explication of associated implications. Many contingencies must be considered in future analysis and capability development to create a balanced force. However, it is imperative that national security professionals consider the likelihood, and implications, of having to undertake future operations in littoral urban centers against evolved irregular threats.