This study deals with the evaluation of four different image-processing software modules for the generation of digital surface models from very high-resolution stereo satellite data. The analysis was done in an urban area due to the growing interest in 3-D information over built-up areas. Depending on the different geometric model approaches used by the different software packages, shifts between 3.06-3.27 m between the digital surface models (DSMs) and the reference DSM were measured. The vertical RMSE of the four tested software packages range between 2.96-14.01 m. However, the visual evaluation resulted in a different ranking and does not confirm the quantitative results entirely. The results show that, depending on the building type to be extracted, the choice of software package may vary. The challenges of automatic DSM extraction in urban areas and the performance of current software package modules to address them are discussed. Potential improvements for automatic DSM extraction in urban areas are identified.