This paper presents the perspective of the Structural Mechanics program of the Air Force Office of Scientific Research on the damage assessment of structures. It is found that damage assessment of structures plays a very important role in assuring the safety and operational readiness of Air Force fleet. The current fleet has many aging aircraft, which poses a considerable challenge for the operators and maintainers. The nondestructive evaluation technology is rather mature and able to detect damage with considerable reliability during the periodic maintenance inspections. The emerging structural health monitoring methodology has great potential, because it will use on-board damage detection sensors and systems, will be able to offer on-demand structural health bulletins. Considerable fundamental and applied research is still needed to enable the development, implementation, and dissemination of structural health monitoring technology.