This paper discusses the reliability of scanning tunneling microscopy (STM) images of mesoscopically rough surfaces. The specific structure of these images represents a convolution between the real surface topography and the shape of the tip. In order to interpret these images quantitatively, the line scans of steep and high steps can be used to obtain an image of the tip itself. This image shows tip radii ranging typically from 5 to 15 nm and cone angles of about 30° over a length of 80 nm, and can in turn be used to recognize the limits of STM resolution on a rough surface: High‐resolution transmission electron microscopy cross‐section images of Au island films on a Au‐Nb double layer are convoluted with the experimentally observed tip shape; the resulting line scans correspond very well with STM graphs of the same samples. Finally an overall criterion for the resolution of the STM on such surfaces is proposed.