An exploratory study was conducted to evaluate construction of synthetic imagery, presented in a binocular, stereoscopic, see-through head-mounted display (HMD) for depicting obstacles commonly encountered in helicopter operations. In Phase 1, participants examined still images to identify obstacles from graphics depicting two levels of ground-plane representation and three levels of object complexity (depth). They then rated the depictions and responded to perspective-view still images of an obstacle field, indicating which areas corresponded with obstruction-free locations. Context played a major role in identifying obstructions, and presence of guy-wire references was important, both for identification of towers and of areas in the forward view that would be free from obstructions. Preliminary flight-simulator trials indicate pilots having experience with power-line flying interpret the representations literally and not schematically or generically.