In some situations, it is difficult to image seismic data even when factors such as illumination, anisotropy, and attenuation are resolvable. An often-overlooked but dominant factor affecting imaging is the geometric complexity of subsurface reflectors. In some of these settings, we propose that geometric complexity plays a dominant role in the quality of seismic imaging. This has been documented in subsalt regions with poor image quality where 3D vertical seismic profiles (VSPs) are available. VSPs often demonstrate that there is good illumination below salt, but the complexity of the observed downgoing wave and diffractions cannot be simulated with smooth earth models. We use synthetic examples with high geometric complexity and no other complications to analyze the imaging process: a 2D sediment-salt model with rough salt-top topography, and a 1D model with complex reflectivity. In these models, it is difficult to estimate velocity, and it is challenging to image the data. These synthetic examples are useful to understand the limitations of imaging with smooth models, to create guidelines to identify geometric complexity in field data, and to develop possible mitigations to improve imaging. Further real data examples will be needed to test geometric complexity.