This paper will demonstrate the imposing challenges and technical solutions of planning, managing, and producing digital orthophotography over a central business district having very tall buildings. The discussion will illustrate proven methodology in photogrammetrically capturing digital elevation model (DEM) data and planimetric features capable of rectifying digital imagery. As evidence of its successful implementation, examples of several actual projects will be displayed using the ArcView 3D Analyst extension. This paper will also show that the resulting imagery meets National Map Accuracy Standards (NMAS) while minimizing building lean and shadows. To accomplish this, several scenarios for acquiring aerial photography will be reviewed.